Dimethylacetamide 分子结构式
HCID31374

Dimethylacetamide

N,N-dimethylacetamide

C4H9NO87.12 g/molCAS 127-19-5

IDENTITY

结构与身份

标准SMILES
CC(=O)N(C)C
InChIKey
FXHOOIRPVKKKFG-UHFFFAOYSA-N
分子式
C4H9NO
平均分子量
87.12 g/mol
单同位素质量
87.06841391

IDENTITY

标识信息

中文名
N,N-二甲基乙酰胺
英文名
N,N-Dimethylacetamide
分子式
C4H9NO
分子量
87.12

ALIASES

名称与别名

乙酰二甲胺二甲基醯胺二甲替乙酰胺二甲基乙酰胺HPLC级N气相顶空级NN-乙酰二甲胺N-二甲基乙酰胺N,N-二甲基乙酰N,N-二甲基乙酰胺DMACDMADimethyl acetamideN,N-Dimethylacetamide, 99%, pureC4H9NOdimethylacetamidCH3CON(CH3)2Acetic acid dimethylacetamideN,N-Dimethylethanamidedimethylacetoneamide

PROPERTIES

物理化学性质

熔点
-20 °C · -20 °C (lit.)
沸点
164.5 · 164.5-166 °C (lit.)
密度
0.937 g/mL · 0.937 g/mL at 25 °C (lit.)
蒸气密度
3.89 · 3.89 (vs air)
蒸气压
40 mm · 40 mm Hg ( 19.4 °C)
折射率
20 · n20/D 1.439(lit.)
闪点
158 °F · 158 °F
储存条件
30 °C · Store below +30°C.
溶解度
1000 g/l · >1000g/l soluble
形态
Liquid
酸度系数(pKa)
-0.41 · -0.41±0.70(Predicted)
颜色
Colorless to yellowish
PH值
4 · 4 (200g/l, H2O, 20℃)
气味 (Odor)
Faint ammonia odor
酸碱指示剂变色ph值范围
4 at · 4 at 200 g/l at 20 °C
相对极性
6.3 · 6.3
外观
Solid Powder
嗅觉阈值(Odor Threshold)
0.76 ppm · 0.76ppm
爆炸极限值(explosive limit)
1.7 · 1.7-11.5%(V)
水溶解性
miscible
热导率
0.168 W/ · 0.168 W/(m·K) at 25 ℃
比热容
2.02 J/ · Cp(liquid): 2.02 J/(g·K), at 25℃
最大波长(λmax)
270 nm · λ: 270 nm Amax: 1.00λ: 280 nm Amax: 0.30λ: 290 nm Amax: 0.15λ: 310 nm Amax: 0.05λ: 320 nm Amax: 0.03λ: 360-400 nm Amax: 0.01
Merck
14 · 14,3227
BRN
1737614 · 1737614
Henry's Law Constant
6.1 · 6.1×101 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
暴露限值
10 ppm · ACGIH:TLV-TWA 10 ppm (36 mg/m3)OSHA:PEL-TWA 10 ppm (35 mg/m3)NIOSH:REL-TWA 10 ppm
介电常数
37.8 · 37.8(25℃)
稳定性
Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
InChIKey
FXHOOIRPVKKKFG-UHFFFAOYSA-N
SMILES
CN(C)C(C)=O
LogP
-0.77 at · -0.77 at 25℃
表面张力
37.13 mN/m · 37.13mN/m at 293.15K
CAS 数据库
127 · 127-19-5(CAS DataBase Reference)
NIST化学物质信息
Acetamide, N,N-dimethyl-(127-19-5)
(IARC)致癌物分类
2 B · 2B (Vol. 123) 2020
EPA化学物质信息
Dimethylacetamide (127-19-5)

SAFETY

安全数据

F
3-10
wgk
WGK 2
tsca
TSCA listed
毒性
LD50 orally in rats: 5.4 ml/kg (Bartsch)
RTECS号
AB7700000
存储类别
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
安全说明
16-24-53-45-36-28-26
海关编码
29241900
自燃温度
914 °F
危险品标志
T
危险性类别
Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Irrit. 2Repr. 1B
危险类别码
11-20/22-61-20/21-36
毒害物质数据
127-19-5(Hazardous Substances Data)
职业暴露等级
A
职业暴露限值
TWA: 10 ppm (35 mg/m3) [skin]
立即威胁生命和健康浓度
300 ppm

PRICE

试剂价格

A10924 · 2500ml
N,N-二甲基乙酰胺(DMAC )N,N-Dimethylacetamide1110元
044913 · 1L
N,N-二甲基乙酰胺N,N-Dimethylacetamide, anhydrous, 99.8%1891元

REFERENCE

应用领域

概述N,N-二甲基乙酰胺又称乙酰基二甲胺、乙酰二甲胺,简称DMAC,是一种非质子高极性溶剂,有微氨气味,溶解力很强,可溶解的物质范围很广,能与水、芳香族化合物、酯、酮、醇、醚、苯和三氯甲烷等任意混溶,且能使化合物分子活化,因此广泛用作溶剂及催化剂。在溶剂方面作为高沸点、高闪点、热稳定性高、化学性稳定的溶剂,可用于聚丙烯腈的抽丝溶剂、合成树脂及天然树脂、甲酸乙烯酯、乙烯基吡啶等共聚物及芳烃羧酸的溶剂;在催化剂方面可用于尿素加热制氰尿酸、卤代烷与金属氰化物反应制腈、乙炔钠与卤代烷反应制烷基炔、有机卤化物与氰酸盐反应制异氰酸酯等过程。N,N-二甲基乙酰胺还可用作电解溶剂及摄影用成色剂的溶剂、脱油漆剂、有机合成原料、农药及医药原料。从C8馏分中分离苯乙烯的萃取蒸馏溶剂等。

用途用作合成纤维的原料及有机合成的优良极性溶剂

用途用于有机合成,也用作溶剂、催化剂和去漆剂

用途DMAC主要用作合成纤维(丙烯腈)和聚氨酯纺丝及合成聚酰胺树脂的溶剂,也用于从C8馏分分离苯乙稀的萃取蒸馏溶剂,并广泛用于高分子薄膜、涂料和医药等方面。目前在医药和农药上大量用来合成抗菌素和农药杀虫剂。还可用作反应的催化剂、电解溶剂、油漆清除剂以及多种结晶性的溶剂加合物和络合物。

用途用于药物合成的反应溶剂,合成纤维纺丝与合成树脂的溶剂,感光化学品发色剂的溶剂,涂料等的溶剂。催化剂。

REFERENCE

化学性质

化学性质无色透明液体。 能与水、醇、醚、酯、苯、三氯甲烷和芳香化合物等有机溶剂任意混合。

REFERENCE

制备方法

生产方法1.乙酐法二甲胺与醋酐在0-20℃时进行酰化反应,然后用液碱低温中和除去醋酸,分离出醋酸钠,中和液再进行碱洗,精馏,取沸程164-166.5℃馏分为成品。原料消耗定额:乙酐(95%)1150kg/t、二甲胺(40%)1898kg/t。2.乙酰氯法由二甲胺与乙酰氯反应,也可制备得到二甲基乙酰胺。该工艺与国内现行乙酐法工艺相比,生产成本降低,经济效益有所提高。3.醋酸法抚顺市化工设备研究院采用醋酸与二甲胺合成法,取得了良好成果。该工艺特点是采用先进的催化反应精馏技术,使反应强化,能耗降低,分离效果和产品收率大大提高,工艺过程简化。该工艺与醋酐法合成二甲基乙酰胺工艺相比,生产成本降低,经济效益有所提高。中国目前多用。4.羰基合成法国外研究将三甲胺和一氧化碳进行羰基化合成,生成N,N-二甲基乙酰胺的方法。反应中用铁、钴、镍的碘化物或溴化物作催化剂。

REFERENCE

毒性防护

急性毒性口服- 大鼠 LD50: 4300 毫克/ 公斤; 口服- 小鼠 LD50: 4620 毫克/ 公斤

刺激数据皮肤- 兔子 10 毫克/ 24小时 轻度; 眼- 兔子 100 毫克 轻度

职业标准TLV-TWA 10 PPM (35 毫克/ 立方米); STEL 15 PPM (50 毫克/ 立方米)

REFERENCE

包装储运

爆炸物危险特性与空气混合可爆

可燃性危险特性遇明火、高温、强氧化剂可燃; 燃烧排放有毒氮氧化物烟雾

储运特性包装完整、轻装轻卸; 库房通风、远离明火、高温、与氧化剂、酸分开存放

灭火剂泡沫、干粉、二氧化碳

UPSTREAM / DOWNSTREAM

上下游产品信息

上游原料

一氧化碳化工机械三水合醋酸钠乙酰氯碘海醇水解物三甲胺醋酸溴化物二甲胺

下游产品

1,2-二氯丙烷杀虫单4-乙酰基-2-硝基噻吩2-甲基-7-氮杂吲哚头孢噻肟钠2-(1-羟基氨基乙基)-苯并噻吩2-乙酰基苯并噻吩3-(苯并呋喃-2-基)-3-羰基丙腈氟西汀1-萘磺酰氯5-乙酰吲哚复合聚苯乙烯高效防腐涂料培高利特1,3-二氯丙烯杀虫环草酸盐头孢哌酮6-溴乙基-喋啶-2,4-二胺1-(3-氨基-2-硫乙基)乙烷-1-酮4-羟基吲哚4'-苯氧基苯乙酮二苯基乙炔苯乙双胍1-氯-2-丙醇氟灭酸头孢地尼2-乙酰基吡咯头孢甲肟2-甲基-4-甲胺基-6-甲氧基均三嗪(±)顺式二氯菊酸4-氟苯胺主链型液晶聚硅氧烷聚氨酯2-乙酰基苯并呋喃色酮-3-甲醛1-甲基-1H-咪唑-5-甲酸6-氨基-3-甲基嘌呤

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COMPUTED

结构计算性质

XLogP
-0.8
极性表面积
20.3 Ų
氢键供体
0
氢键受体
1
可旋转键
0
重原子
6
形式电荷
0
复杂度
58

PROPERTIES

实验与物化性质

LogP

log Kow= -0.77

-0.77

Odor

AMINE

Weak, ammonia- or fish-like odor

Density

0.943 at 68 °F (USCG, 1999) - Less dense than water; will float

0.937 (USCG, 1999) - Less dense than water; will float

0.9366 @ 25 °C/4 °C

Relative density (water = 1): 0.94

0.94

0.943 @ 20°C

Viscosity

0.92 cP @ 25 °C

Color/Form

Liquid

OILY

Colorless liquid

Solubility

greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)

SOL IN BENZENE

Soluble in alcohol, acetone, ether

Miscible with most org solvents

MISCIBLE WITH AROMATIC CMPD, ESTERS, KETONES, ETHERS

Miscible in water.

Flash Point

151 °F (NTP, 1992)

145 °F (USCG, 1999)

70 °C

70 °C (OPEN CUP)

63 °C c.c.

158 °F (open cup)

Boiling Point

329 to 331 °F at 760 mmHg (NTP, 1992)

331 °F at 760 mmHg (USCG, 1999)

163-165 °C

165 °C

329 °F

165 °C @760 [mm Hg]

Decomposition

ON DECOMPOSITION CAN EMIT FUMES HIGHLY IRRITATING TO EYES, MUCOUS MEMBRANES.

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

Melting Point

-4 °F (NTP, 1992)

-4 °F (USCG, 1999)

-18.59 °C

-20 °C

-4 °F

-20 °C

Vapor Density

3.01 (Air= 1)

Relative vapor density (air = 1): 3.01

Odor Threshold

Odor Threshold Low: 21.0 [ppm];Odor Threshold High: 47.0 [ppm];Odor threshold from "Quick Guide: The Electronic NIOSH Pocket Guide to Chemical Hazards"

ODOR THRESHOLD FOR 50% RESPONSE IS 21.4 PPM; FOR 100% RESPONSE, 46.8 PPM.

Odor low: 163.8 mg/cu m; Odor high: 163.8 mg/cu m

GHS

GHS分类

GHS Classification

Danger

H312: Harmful in contact with skin [Warning Acute toxicity, dermal];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H360D ***: May damage the unborn child [Danger Reproductive toxicity]

P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

HAZARDS

危害信息

Regulatory Information

Chemical: Acetamide, N,N-dimethyl-

Hazard Traits - Carcinogenicity; Developmental Toxicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; Prop 65;Report - regardless of intended function of ingredient in the product

Acetamide, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetamide, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15266

Restricted substance: N,N-dimethylacetamide (DMAC);EC: 204-826-4;Restriction condition document: PDF link

Substance: N,N-dimethylacetamide;EC: 204-826-4;Date of inclusion: >19-Dec-2011;Reason for inclusion: Toxic for reproduction (Article 57c)

Other Safety Information

IMAP assessments - Acetamide, N,N-dimethyl-: Human health tier II assessment;IMAP assessments - Acetamide, N,N-dimethyl-: Environment tier I assessment

DOT Label

Combustible Liquid

Poison

Fire Hazards

This chemical is combustible. (NTP, 1992)

Special Hazards of Combustion Products: Emits carbon oxides, nitrogen oxides, and dimethylamine when heated to decomposition.;Behavior in Fire: Sealed closed containers may rupture from pressure from heat of fire. (USCG, 1999)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 63 °C explosive vapour/air mixtures may be formed.

Fire Potential

Combustible when exposed to heat or flame.

Health Hazards

Liquid causes mild irritation of eyes and skin. Ingestion causes depression, lethargy, confusion and disorientation, visual and auditory hallucinations, perceptual distortions, delusions, emotional detachment, and affective blunting. (USCG, 1999)

Inhalation may cause nasal and respiratory irritation. May cause systemic poisoning. Ingestion may cause abdominal spasms, vomiting, sweating, weakness, and headache. Large doses may cause lethargy, disorientation, redness, dermatitis, and sensitization. (USCG, 1999)

Hazards Summary

Toxic hepatitis has been reported in workers after inhalation and dermal exposure. DMAC is fetotoxic and teratogenic when administered at high doses to rabbits and rats. NOAEL = 25 ppm for hepatic and renal toxicity in rats and mice. Humans exposed to high doses may experience mental confusion. [ACGIH] A skin and eye irritant; Inhalation of high concentrations may cause liver and CNS effects; [ICSC] In a study of 440 new elastone fiber workers, 28 cases with elevated liver enzymes were detected in a 31 month period from 2002 to 2004. Using the BEI of 30 mg/g creatinine as a cutoff, the incidence of hepatic injury was about 7 times greater in the high exposure group. [Reference #1]

Reactive Group

Amides and Imides

Amides and Imides;Water and Aqueous Solutions

EC Classification

Note: E; Symbol: T; R: 61-20/21; S: 53-45

Special Reports

CENT CHEM HAZARD ASSESSMENT, SYRACUSE; INFORMATION PROFILES ON POTENTIAL OCCUPATIONAL HAZARDS. VOLUME I. SINGLE CHEMICALS. N,N-DIMETHYL ACETAMIDE; REPORT; ORDER NUMBER PB81-148009, 14 PP (1979). REVIEW OF KNOWN & SUSPECTED HEALTH EFFECTS, EXTENTS OF WORKER EXPOSURE, & INDUSTRIAL IMPORTANCE.

TSCA Requirements

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N,N-Dimethylacetamide is included on this list.

OSHA Standards

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 10 ppm (35 mg/cu m). Skin Designation.

SAFETY

安全与防护

Fire Fighting

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Fire Extinguishing Agents Not to Be Used: Do not use halogenated extinguishing media or water.;Fire Extinguishing Agents: Dry chemical, alcohol foam, carbon dioxide (USCG, 1999)

Use powder, alcohol-resistant foam, water spray, carbon dioxide.

First Aid Measures

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Seek medical attention if you feel unwell.

First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Call for medical aid.;EYES: Flush with plenty of water for 15 min., lifting lids occasionally.;SKIN: Flush with plenty of water for 15 min. Remove contaminated clothing and shoes.;INGESTION: Induce vomiting. (USCG, 1999)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water flush immediately - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe Storage

Ventilation along the floor. Separated from strong oxidants.

Exposure Control and Personal Protection

Biological Exposure Indices (BEI) [ACGIH] - M-Methylacetamide in urine = 30 mg/g creatinine; end of shift at end of workweek;

5.0 [ppm]

Fire Fighting Procedures

EXTINGUISH WITH WATER, DRY CHEMICALS, ALCOHOL FOAM OR CARBON DIOXIDE

Storage Conditions

MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ... .

Cleanup Methods

1. Ventilate the area of spill or leak. 2. For small quantities, absorb on paper towels. Evaporate in safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn paper in suitable location away from combustible materials.

Nonfire Spill Response

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.;LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

1. By absorbing it in vermiculite, dry sand, earth or a similar material and disposing in sealed containers in secured sanitary landfill. 2. By atomizing in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.

Spillage Disposal

Personal protection: chemical protection suit. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed or replaced.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

TOXICITY

毒理信息

Body Burden

N,N-dimethylacetamide was qualitatively found in 8 of 12 breath samples of subjects monitored in Bayonne and Elizabeth, NJ, and Research Triangle Park, NC, 1980(1).

Interactions

DAILY INJECTIONS OF PROGESTERONE (5 MG/HAMSTER/DAY, FOR 4 DAYS) BLOCKED ANTIFERTILITY EFFECT OF DMA (ADMIN @ NIDATION) AS DID INJECTIONS OF A LUTEOTROPIC COMPLEX (1 MG/HAMSTER/DAY PROLACTIN PLUS 5.1 IU/HAMSTER/DAY OF PREGNANT MARE SERUM GONADOTROPIN, FOR 4 DAYS.

DIMETHYLACETAMIDE LOWERED THE YIELDS AND/OR INCIDENCES OF TOTAL TUMORS, BENIGN PLAQUES, BENIGN HYPERKERATOTIC LESIONS AND ADVANCED TUMORS PROMOTED BY RETINYL ACETATE OR CROTON OIL AFTER INITIATION BY 7,12-DIMETHYLBENZ(A)ANTHRACENE.

SINGLE EXPT WITH 45 MG/KG RAT OF PYRIMETHAMINE ISETHIONATE IN 6% DIMETHYLACETAMIDE, 6% DIMETHYL SULFOXIDE OR 95% ETHANOL SHOWED THAT TERATOGENIC EFFECT WAS CUMULATIVE IN DIMETHYL SULFOXIDE OR ETHANOL BUT AFTER ADMIN IN DMA RESPONSE-DOSE RELATION FOLLOWED A PARABOLIC CURVE.

PCC4azal embryonal carcinoma tumors were grown in strain 129 mice by sc transplantation. When palpable, the tumors were treated with a combination of retinoic acid and dimethylacetamide. In vitro, this embryonal carcinoma cell line shows minimal spontaneous differentiation and is exquistely sensitive to retinoic acid and/or dimethylacetamide induction of differentiation. Ten daily 20 ul intratumor injections of a solution of 10 mg retinoic acid per ml of dimethylacetamide resulted in nearly complete induction of morphological differentiation mainly into neuropithelial and glandular derivatives. Control tumors showed minor spontaneous differentiation. Differentiation was associated with decreased tumor growth rate, decreased mitotic index, decreased extent of necrosis, and increased survival time of the hosts. In 4 of 18 cases, long-term survival of the hosts was effected by a complete differentiation of the malignant embryonal carcinoma tumors into benign teratomas. Retinoic acid: dimethylacetamide was also effective in inducing differentiation with the same dosage and schedule when admin systemically, ie, ip or sc.

Target Organs

Skin, liver, central nervous system

Ecotoxicity Values

LC50 Pimephales promelas (fathead minnow) 1.50 g/l/96 hr (confidence limit 1.21- 1.86 g/l), flow-through bioassay with measured concentrations, 23.1 °C, dissolved oxygen 6.6 mg/l, hardness 45.0 mg/l calcium carbonate, alkalinity 43.5 mg/l calcium carbonate, and pH 7.7.

Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that N,N-dimethylacetamide is expected to have very high mobility in soil(SRC). Volatilization of N,N-dimethylacetamide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.31X10-8 atm-cu m/mole(4). The potential for volatilization of N,N-dimethylacetamide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2 mm Hg(5). N,N-Dimethylacetamide is expected to be biodegradable in soil based on aqueous screening tests(6,7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that N,N- dimethylacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.31X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). N,N-Dimethylacetamide, present at 100 mg/l reached 28% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(7). N,N-Dimethylacetamide, present at 30 mg/l, reached 80% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/l and the Japanese MITI test(7). In other studies, N,N-dimethylacetamide, present at 400 mg/l, reached 96% of its theoretical TOC in 5 days using industrial activated sludge(8). These results from laboratory studies suggest that N,N-dimethylacetamide will biodegrade in the aquatic environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-dimethylacetamide, which has a vapor pressure of 2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase N,N-dimethylacetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is 28 hours(SRC), calculated from its rate constant of 1.36X10-11 cu cm/molecule-sec at 25 °C(3).

Adverse Effects

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.;Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.;IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.;ACGIH Carcinogen - Confirmed Animal.

Exposure Routes

The substance can be absorbed into the body by inhalation and through the skin.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms

Headache. Nausea.

MAY BE ABSORBED! Redness. Further see Inhalation.

Abdominal cramps. Diarrhoea. Further see Inhalation.

irritation skin; jaundice, liver damage; depression, drowsiness, hallucinations, delusions

Medical Surveillance

The determination of urinary N-monomethylacetamide in the end of shift urine sample was used to monitor exposure to dimethylacetamide. Five workers were observed followed for 4 consecutive weeks. Airborne dimethylacetamide appeared to account for the greatest amount of urinary N-monomethylacetamide detected and, at the exposure concentrations encountered (0.5 to 2 ppm), a relationship of 10 ppm urinary N-monomethylacetamide inhaled was observed. Interindividual variation was small and no evidence of build-up in N-monomethylacetamide urinary levels was seen in these subjects. Mean airborne dimethylacetamide concentrations were somewhat higher by the end of the week, but magnitude was such that the differences were not statistically significant. It is concluded that changes in dimethylacetamide exposures can be quantitatively reflected by urinary N-monomethylacetamide.

A study of occupational exposure to dimethylactamide was conducted using both biological and environmental monitoring techniques. Personal and area air samples were analyzed for dimethylacetamide at a facililty manufacturing prefabricated synthetic products. Spot urine samples were collected from eight exposed and four unexposed workers for 5 consecutive work days and on the following Monday. These were analyzed for N-methylacetamide, a dimethylacetamide metabolite. Area air dimethylacetamide concentrations were generally constant, ranging from 11.81 to 17.24 ppm with a mean of 14.74 ppm. Personal dimethylacetamide concentrations showed a wide variability. The concentrations were distributed log normally with arithmetic and geometric means of 14.0 and 6.0 ppm, respectively. Urinary N-methylacetamide concentrations were not correlated with personal air dimethylacetamide concentrations. Six of the exposed workers excreted about 18% of the inhaled dimethylacetamide dose, calculated as the 8 hr time weighted average exposure, as N-methylacetamide. The other two exposed workers excreted about 30 percent of the inhaled dose as N-methylacetamide. Urinary N-methylacetamide concentrations the Monday following exposure were negligible or had returned to their preexposure values. Based on these results the half life for urinary excretion of N-methylacetamide was calculated to be 16 hours. The authors conclude that for dimethylacetamide and similar substances that are easily absorbed through the skin, biological monitoring is superior to airborne exposure monitoring for determining total uptake and evaluating potential health risks.

the assessment of dimethylacetamide exposure can be accomplished through measurement of either dimethylacetamide, N-methylacetamide (NMAC), or acetamide. Urinary levels of NMAC have been shown to correlate with airborne exposure levels of dimethylacetamide. However, no information was located which showed a correlation between urinary NMAC levels & the onset of adverse health effects. Urine Reference Ranges: Normal- None detected; Exposed- BEI (sampling time is end of shift at the end of workweek, measured as N-methylacetamide): 30 mg/g creatinine; Toxic- Not established.

Liver Function Tests: Biochemical tests - Enzymes that reflect cholestasis: alkaline phosphatase (AP), 5'-nucleotidase (5'-NT) & leucine aminopeptidase (LAP); Enzymes that detect direct hepatic damage: aspartate aminotransferase (AST), alanine aminotransferase (ALT) & gammma glutamyl Transpeptidase (GGTP); Clearance tests - indocyanine green, antipyrine test and serum bile acids.

Soil Adsorption/Mobility

The Koc of N,N-dimethylacetamide is estimated as 9(SRC), using a measured log Kow of -0.77(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N,N-dimethylacetamide is expected to have very high mobility in soil(SRC).

Atmospheric Concentrations

SOURCE DOMINATED: N,N-Dimethylacetamide was detected in 6 of 6 air samples in 1982 within a mile radius of a hazardous liquid waste impoundment, location not given, at concns ranging from 9.6 ng/cu m to 11 ng/cu m(1).

Human Toxicity Excerpts

CERTAIN N-SUBSTITUTED AMIDES ... DIMETHYL ACETAMIDE, MAY PRODUCE CHRONIC LIVER OR RENAL DAMAGE.

JAUNDICE HAS BEEN OBSERVED ... IN WORKERS EXPOSED REPEATEDLY AT ... 20-25 PPM ... SKIN PENETRATION UNDOUBTEDLY CONTRIBUTED TO THIS EFFECT.

... GIVEN TO HUMANS IN DAILY DOSES OF 400 MG/KG FOR 3 OR MORE DAYS ... DEPRESSION, LETHARGY, CONFUSION & DISORIENTATION ENSUED. IN SOME ... VISUAL & AUDITORY HALLUCINATIONS, PERCEPTUAL DISTORTIONS, DELUSIONS, EMOTIONAL DETACHMENT & AFFECTIVE BLUNTING ... .

DIZZINESS, SLEEPINESS, & WEAKNESS RESULTED FROM DMA CONCN OF 109.5-337 MG/CU M IN AIR OF METAL SURFACE FINISHING PROCESSES.

For more Human Toxicity Excerpts (Complete) data for N,N-DIMETHYLACETAMIDE (17 total), please visit the HSDB record page.

REGULATORY

法规信息

Regulatory Information

Chemical: Acetamide, N,N-dimethyl-

Hazard Traits - Carcinogenicity; Developmental Toxicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; Prop 65;Report - regardless of intended function of ingredient in the product

Acetamide, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetamide, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15266

Restricted substance: N,N-dimethylacetamide (DMAC);EC: 204-826-4;Restriction condition document: PDF link

Substance: N,N-dimethylacetamide;EC: 204-826-4;Date of inclusion: >19-Dec-2011;Reason for inclusion: Toxic for reproduction (Article 57c)

TSCA Requirements

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N,N-Dimethylacetamide is included on this list.

PHARMACOLOGY

药理信息

Metabolism/Metabolites

N-DEMETHYLATION OF ... DIMETHYLACETAMIDE OCCURRED IN RAT, RESPECTIVE MONOMETHYLAMIDES APPEARING IN URINE ... IN THE CASE OF DIMETHYLACETAMIDE WAS DIDEMETHYLATED PRODUCT, ACETAMIDE, ALSO FOUND.

ANALYSIS OF HUMAN URINE AFTER OCCUPATIONAL EXPOSURE TO DIMETHYLACETAMIDE SHOWS N-METHYLACETAMINE. /FROM TABLE/

Gas chromatographic analysis of the urine of rats which had received dimethylacetamide by the subcutaneous route indicated the presence of N-methyl-acetamide and acetamide. Both metabolites were also found ... in incubation mixtures of dimethylacetamide with rat liver homogenate. N-Methylacetamide was detected in the urine of human volunteers who had inhaled dimethylacetamide or absorbed dimethylacetamide vapor through the skin. Measurement of the amount of the metabolite N-methylacetamide excreted by individuals exposed to dimethylacetamide vapors with or without face masks which allowed the inhalation of air free of dimethylacetamide indicated that more dimethylacetamide was absorbed through the lung than through the skin. ... Only 2-10% of the amount of dimethylacetamide inhaled was recovered in the urine in the form of N-methylacetamide. It has been suggested that the major urinary metabolite of the analogous dimethylformamide is N-(hydroxymethyl)-N-methylformamide and not N-methylformamide, since the carbinolamide decomposes on the gas chromatography column (to N-methylformamide) but is relatively stable in aqueous solution. In analogy, it would be logical to assume that the N-methylacetamide found in the urine after exposure to dimethylacetamide really arose from chemical breakdown of N-(hydroxymethyl)-N-methylacetamide during the analytical process.

N,N-dimethylacetamide is metabolized by demethylation first to monomethyl derivatives and then to the parent acetamide.

MeSH Pharmacological Classification

Substances that provide protection against the harmful effects of freezing temperatures.

Absorption, Distribution and Excretion

/N,N-DIMETHYLACETAMIDE/ ... READILY ABSORBED THROUGH SKIN ... .

N,N-dimethylacetamide is rapidly absorbed through biological membranes.

No correlation between personal airborne exposure and excretion of mono-methylacetamide in urine was detected during a full workshift (5 days). Most (n = 6) workers studied (n = 8) excreted about 13% of the calculated inhaled dose as metabolite in urine.

DMAC is readily absorbed in man after oral, dermal, or inhalation exposure. ... About 2% of a dose of dimethylacetamide is recovered in the urine as MMAC /N-methylacetamide/ after inhalation; 10% is recovered after inhalation plus skin exposure. Exposure to 10 ppm of DMAC results in complete excretion of MMAC with in 30 hr. Maximal concns of 45 & 100 ppm (mg/L) of MMAC in the urine are found in subjects exposed both by inhalation & skin. In workers continuously exposed to DMAC vapor (inhalation plus skin) & subjected to DMAC airborne levels of 6-22 ppm ..., about 13.5% of the estimated dose is excreted as MMAC in the urine. Some workers may excrete about 30% of a dose as MMAC.

For more Absorption, Distribution and Excretion (Complete) data for N,N-DIMETHYLACETAMIDE (7 total), please visit the HSDB record page.

USES

用途与制造

Uses

Used as a solvent for many organic reactions, resins, polymers, crystallization, and purification. [ACGIH] Used as a solvent in plastics, resins, and gums; Also used as a catalyst and paint remover; [Hawley] Used in synthetic fiber and resin industries; Used as a solvent in elastane fiber factories; [Reference #1]

Semiconductor Manufacturing [Category: Industry];Plastic Composites Manufacturing [Category: Industry]

Solvent in industrial applications

Solvent for plastics, resins, gums, and electrolytes; catalyst; paint remover; high-purity solvent for crystallization and purification

N,N-Dimethylacetamide is used to dissolve polyacrylonitrile, polyvinyl chloride, polyamides, polyimides, cellulose derivatives, styrenes, and linear polyesters; manufacturing of films and fibers; booster solvent in coatings and adhesives formulations.

Electrolytic solvent; formation of dimethylacetamide complexes; chemical reaction medium and catalyst

U.S. Production

2023: 25,000,000 - <40,000,000 lb;2022: 70,000,000 - <85,000,000 lb;2021: 70,000,000 - <85,000,000 lb;2020: 55,000,000 - <70,000,000 lb

(1972) GREATER THAN 4.54X10+5 GRAMS

Consumer Uses

Semiconductor and photovoltaic agent;Solvent;Intermediate;Not Known or Reasonably Ascertainable

Industry Uses

Not Known or Reasonably Ascertainable;Soil amendments (fertilizers);Laboratory chemicals;Intermediate;Binder;Solvent;Fuel agents;Semiconductor and photovoltaic agent

Methods of Manufacturing

From tris(dimethylamido)phosphate and acetic anhydride. From acetic anhydride and dimethylformamide.

By reaction of acetic acid and dimethylamine.

Reaction of methyl acetate and dimethylamine; reaction of dimethylamine with the azotrope of methyl acetate and methanol.

Reaction of N,N-dimethylamine and acetic anhydride.

Formulations/Preparations

Grades: ... high purity certified.

General Manufacturing Information

Pharmaceutical and Medicine Manufacturing;Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing;Plastics Product Manufacturing;Electrical Equipment, Appliance, and Component Manufacturing;Agriculture, Forestry, Fishing and Hunting;Wholesale and Retail Trade;Plastics Material and Resin Manufacturing;All Other Chemical Product and Preparation Manufacturing;Miscellaneous Manufacturing;Organic Fiber Manufacturing;All Other Basic Organic Chemical Manufacturing;Textiles, apparel, and leather manufacturing;Services

Acetamide, N,N-dimethyl-: ACTIVE

COMPOUNDS THAT HAVE BEEN SUGGESTED AS SOLVENTS OR SUSPENDING AGENTS IN TESTS OF DERMAL TOXICITY ... /INCLUDE/ DIMETHYLACETAMID.

TESTED AS DRUG VEHICLE & AS ANTITUMOR AGENT

SOLVENT FOR STABILIZATION OF PROSTAGLANDINS IN SOLUTION

ALIASES

名称与别名

共 136 条
N,N-DIMETHYLACETAMIDE127-19-5DimethylacetamideAcetamide, N,N-dimethyl-AcetdimethylamideDMAcDimethyl acetamideN,N-Dimethyl acetamideDimethylamide acetateN,N-DimethylethanamideDimethylacetone amideAcetic acid, dimethylamideAcetyldimethylamineNSC 3138Acetic acid dimethylamideCBC 510337DTXSID5020499SK 7176Dimethylamid kyseliny octoveU-5954

REACTIONS

相关反应

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HRID 7 反应方程式

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HRID 8 反应方程式

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HRID 21 反应方程式

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HRID 63 反应方程式

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HRID 79 反应方程式

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HRID 80 反应方程式

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