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N-メチルアセトアミド

N-Methylacetamide

HCID 6582
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
79-16-3
標準SMILES
CNC(C)=O
InChIKey
OHLUUHNLEMFGTQ-UHFFFAOYSA-N
分子式
C3H7NO
平均分子量
73.09 g/mol
単同位体質量
73.05276385

概要

N-methylacetamide is a monocarboxylic acid amide that is the N-methyl derivative of acetamide. It has a role as a metabolite. It is a member of acetamides and a monocarboxylic acid amide. It is functionally related to an acetamide.

名称と識別子

優先名称
N-Methylacetamide
IUPAC
N-methylacetamide
現地名
N-メチルアセトアミド
英語名
N-Methylacetamide
分子式
C3H7NO
分子量
73.09

名称と別名

N-METHYLACETAMIDE79-16-3MethylacetamideAcetamide, N-methyl-MonomethylacetamideMethyl acetamideN-Methyl acetamideAcetamide, methyl-N-MonomethylacetamideAcetic acid, amide, N-methylDTXSID0047167NSC-747
名称をさらに表示
N-メチルアセトアミド1-(メチルイミノ)エタノールメチルアセチルアミンアセチルメチルアミンN-メチルアセトアミド(NMA)N-アセチル-N-メチルアミンN‐メチルアセトアミドNMACH3CONHCH3dpgsN-MethylacetaMACETMETHYLAMIDEmethyl-acetamid
V0T777481MDTXCID8027167CHEBI:87321RefChem:163783201-182-6AcetylmethylamineN-Acetyl-N-methylamineX 44

データベース識別子

CAS
79-16-3
PubChem CID
6582
DTXSID
DTXSID0047167
ChEMBL
CHEMBL11544
ChEBI
CHEBI:87321
UNII
V0T777481M
EC Number
201-182-6
Nikkaji
J1.964J、J2.141.814E

物性

構造計算による物性補完中

XLogP
-1.1
極性表面積
29.1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
5
形式電荷
0
複雑度
42.2

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 件

log Kow = -1.05

-1.05

Density0.9371 @ 25 °C/4 °C
Viscosity3.65 centipose (30 °C); 3.23 centipose (35 °C); 3.012 centipose (40 °C)
Color/FormNEEDLES
Solubility · 3 件

SOL IN CHLOROFORM

Soluble in alcohol, ether, acetone, benzene

In water, 1X10+6 mg/l @ 20 °C

Flash Point108 °C
Boiling Point205 °C
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point28 °C
Vapor Pressure

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H360D ***: May damage the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Danger

H360 (97.5%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Acetamide, N-methyl-

Hazard Traits - Reproductive Toxicity

REACH registered substance: N-methylacetamide (EC: 201-182-6)

Substance: N-methylacetamide

Methylacetamide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Acetamide, N-methyl-: Human health tier II assessment
Hazards Summary · 1 件

Mice that died 24-48 hours following administration exhibited toxic hepatitis, necrosis of pancreas, and testicular atrophy; Causes hyperglycemia in rats; A diabetogen in experimental animals that produces an insulin-resistant state (rather than insulin deficiency); Teratogenic effects and embryotoxicity observed in rats and rabbits (dermal, gavage, and intraperitoneal routes); [HSDB] Causes changes in renal tubules, changes in bone marrow, and weight loss in 90-day constant feeding study of rats (90 gm/kg); [RTECS] An irritant; [Alfa Aesar MSDS]

Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Hazard Classes and Categories · 5 件

Repr. 1B (97.5%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 2

Reproductive toxicity - Category 1B

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

MONOMETHYLACETAMIDE IS A METABOLITE OF DIMETHYLACETAMIDE & APPEARS IN MEASURABLE AMOUNTS IN URINE AFTER SINGLE EXPOSURE TO A TLV (THRESHOLD LIMIT VALUE) DOSE OF DIMETHYLACETAMIDE.

In a recent comparative toxicity & metab study of 4 formamides & on N-methylacetamide, the sole metabolite of N-methylacetamide in the urine of mice was identified as N-(hydroxymethyl)acetamide. There was no evidence of induction of hepatic drug metabolizing enzymes in rats following treatment with N-methylacetamide. N-Methylacetamide influenced neither the sleeping time induced by hexobarbital nor the metabolism of hexobarbital or aniline.

Absorption, Distribution and Excretion · 1 件

The determination of urinary N-monomethylacetamide (MMAC) in the end of shift urine sample was used to /evaluate/ worker exposure to dimethylacetamide (DMAC). Five workers were observed and followed for 4 consecutive weeks. Airborne DMAC appeared to account for the greatest amount of urinary MMAC detected, and at the exposure concn encountered ().5 to 2 ppm), a relationship of 10 ppm urinary MMAC for each 1 ppm DMAC inhaled was observed. ... It was concluded that changes in DMAC exposures can be quantitatively reflected by urinary MMAC.

用途と製造

Uses · 5 件

Used as a solvent, in electrochemistry, and as a pesticide registered with the EPA; [HSDB]

Farming (Pesticides) [Category: Industry]

For N-Methylacetamide (USEPA/OPP Pesticide Code: 067301) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Solvent

Electrochemistry

U.S. Production(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS
Methods of ManufacturingAcetic acid + methylamine (amide formation)

関連反応

85 件
反応記録を作成
HRID 6083 の反応式
HRID 6083反応物としてuspto-grants-1993_09
HRID 65470 の反応式
HRID 65470反応物としてuspto-grants-1986_09
HRID 129893 の反応式
HRID 129893反応物としてuspto-grants-1995_11
HRID 145338 の反応式
HRID 145338反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 186566 の反応式
HRID 186566反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 197852 の反応式
HRID 197852反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 207460 の反応式
HRID 207460反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 220601 の反応式
HRID 220601反応物としてuspto-grants-2012_06
1 / 11 ページ

化合物ノート

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· 2 件

0.44 [mmHg]

0.44 mm Hg at 23 °C.

物理化学的性質

融点
26 · 26-28 °C (lit.)
沸点
204 · 204-206 °C (lit.)
比重(密度)
0.957 g/mL · 0.957 g/mL at 25 °C (lit.)
蒸気圧
12 · 12-3680Pa at 15-113℃
屈折率
20 · n20/D 1.433(lit.)
闪点
227 °F · 227 °F
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
エタノール、エーテル、アセトン、水、クロロホルム、ベンゼンと混和
酸解離定数(Pka)
16.61 · 16.61±0.46(Predicted)
外見
個体
色
無色 低融点
PH
7 · 7 (H2O)
爆発限界(explosive limit)
3.2 · 3.2-18.1%(V)
水溶解度
溶ける
BRN
1071255 · 1071255
Henry's Law Constant
2.1 · 2.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
Dielectric constant
178.9 · 178.90000000000001
安定性
安定。可燃性。強力な酸化剤とは相容れない。
InChI
1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)
InChIKey
OHLUUHNLEMFGTQ-UHFFFAOYSA-N
SMILES
CNC(C)=O
LogP
-1.05 · -1.05--0.7 at 25℃
表面張力
34.13 mN/m · 34.13mN/m at 293.15K
CAS データベース
79 · 79-16-3(CAS DataBase Reference)
NISTの化学物質情報
Acetamide, N-methyl-(79-16-3)
EPAの化学物質情報
N-Methylacetamide (79-16-3)

化学的性質

化学的特性colourless liquid or solid. Soluble in water, ethanol, benzene, ether, chloroform, insoluble in petroleum ether.

Repr. 1B

Critical Temperature and PressureCritical temperature: 417 °C

安全と保護具

Disposal Methods · 1 件

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.

毒性情報

Interactions · 1 件

SIMULTANEOUS TREATMENT OF PREGNANT RATS WITH SODIUM NITRITE IN DRINKING WATER & N-METHYLACETAMIDE PRODUCED GREATER TERATOGENIC EFFECTS THAN TREATMENT WITH N-METHYLACETAMIDE ALONE. THUS, ENDOGENOUS NITRATION OF CMPD MAY BE TERATOGENIC FACTOR.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a log Kow of -1.05(2) and a regression-derived equation(3), indicates that N-methylacetamide is expected to have very high mobility in soil(SRC). Volatilization of N-methylacetamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.23X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.44 mm Hg(4), and water solubility, 1.0X10+6 mg/l(5). N-Methylacetamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.44 mm Hg(4). N-Methylacetamide (at 100 ppm), exposed to an activated sludge inoculum for two weeks under aerobic conditions, was categorized as biodegradable(6) and is expected to biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from an measured log Kow of -1.05(2) and a regression-derived equation(3), indicates that N-methylacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.23X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.44 mm Hg(4), and water solubility, 1.0X10+6 mg/l(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). N-Methylacetamide (at 100 ppm), exposed to an activated sludge inoculum for two weeks under aerobic conditions, was categorized as biodegradable(8), and is expected to biodegrade in water(SRC). N-Methylacetamide (at 50 ppm carbon), under anaerobic conditions, was not biodegraded over a 4 week period using a 10% activated sludge inoculum(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-methylacetamide, which has a vapor pressure of 0.44 mm Hg at 23 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase N-methylacetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.1 days(SRC), calculated from its rate constant of 5.2X10-12 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Soil Adsorption/Mobility · 1 件

The Koc of N-methylacetamide is estimated as 6(SRC), using a log Kow of -1.05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N-methylacetamide is expected to have very high mobility in soil(SRC).

Human Toxicity Excerpts · 1 件

/Liver toxicity was assessed in/ workers /exposed/ to N,N-dimethylacetamide (DMAC) in an acrylic fiber manufacturing facility. /Measurements were made/ over a 1 yr study period. ... Evidence of liver toxicity was assessed by serum clinical chemistry tests (serum levels of total bilirubin, aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, & gamma-glutamyl transpeptidase) at least once during the study period for all 127 male workers in the two study departments & for 217 male in plant controls with no previous or current exposure to DMAC. If a worker's biomonitoring results exceeded one of two trigger values established for the study (60 mg N-methylacetamide/g creatinine or 136 mg DMAC equivalent/g creatinine), addnl serum clinical chemistry tests were conducted at weekly intervals for 3 wk. DMAC exposed workers were classified as either high exposure, if 1 or more biomonitoring result exceeded one of the trigger values, or unspecified exposure if none of them did. Control group employees were classified as no exposure. Mean DMAC in air levels for the high & unspecified exposure groups appeared to differ (geometric mean DMAC in air levels of 1.9 & 1.3 ppm 12 hr time weighted avg, respectively). No significant DMAC exposure related trends in hepatic serum clinical chemistry results were detected. Neither transient incr in serum analyte levels after a high biomonitoring result (one that exceeded a trigger value) nor an elevated mean level over the study period when compared with in plant controls were observed. These results /indicate/ that brief threshold limit value level exposures & chronic low level exposure (maximum likelihood estimate of the arithmetic mean for DMAC in air for the high exposure group over the study period was 3.0 ppm 12 hr time weighted avg) do not cause hepatotoxic clinical chemistry responses. /N,N-dimethylacetamide/

Artificial Pollution SourcesN-Methylacetamide's production and use as a solvent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

AEROBIC: N-Methylacetamide (at 100 ppm), exposed to an activated sludge inoculum for two weeks under aerobic conditions, was categorized as biodegradable(1). ANAEROBIC: N-Methylacetamide (at 50 ppm carbon), under anaerobic conditions, was not biodegraded over a 4 week period using a 10% activated sludge inoculum(2).

Environmental Bioconcentration · 1 件

An estimated BCF of 2 was calculated for N-methylacetamide(SRC), using a log Kow of -1.05(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for N-methylacetamide is estimated as 4.23X10-8 atm-cu m/mole(SRC) based upon its vapor pressure, 0.44 mm Hg(1), and water solubility, 1.0X10+6 mg/l(2). This Henry's Law constant indicates that N-methylacetamide is expected to be essentially nonvolatile from water surfaces(3). N-Methylacetamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.44 mm Hg(1).

Non-Human Toxicity Excerpts · 5 件

6 AMIDE-TYPE SOLVENTS INCLUDING N-METHYLACETAMIDE WERE APPLIED TO SKIN OF PREGNANT RATS DURING PERIOD OF FETAL ORGANOGENESIS. SLIGHT TERATOGENIC EFFECTS WERE DEMONSTRATED & SLIGHT EMBRYO MORTALITY WAS FOUND WITH N-METHYLACETAMIDE.

WHEN AQUEOUS SOLN OF ACETAMIDES & FORMAMIDES WERE ADMIN BY STOMACH TUBE TO PREGNANT RABBITS FROM 6TH TO 18TH DAY PAST INSEMINATION. BOTH THE ADULT RABBITS AND THE FETUSES WERE EXAMINED FOR EMBRYOTOXIC OR TERATOGENIC EFFECTS. THIS INCLUDED BODY WEIGHT AND WEIGHT GAIN, CONCEPTION RATE, MALFORMATION OF FETUSES, AND THE NUMBERS OF LIVING AND DEAD EMBRYOS PER RABBIT. FOR THE ACETAMIDE DERIVATIVES, THE MONOMETHYL DERIVATIVE HAD THE GREATEST TERATOGENIC EFFECT.

ANIMALS WHICH DIED 24-48 HR AFTER ADMIN OF N-METHYLACETAMIDE HAD TOXIC HEPATITIS, NECROSIS OF PANCREAS & SPLEEN LYMPHOCYTES, & TESTICULAR ATROPHY IN MICE.

SC INJECTIONS OF N-MONOMETHYLACETAMIDE 10 ML OF A 12% SOLN/KG/DAY FOR 4 DAYS INTO NORMAL & ADRENALECTOMIZED RATS PRODUCED HYPERGLYCEMIA DUE TO REDUCED EFFECTIVENESS OF ENDOGENOUS INSULIN.

For more Non-Human Toxicity Excerpts (Complete) data for N-METHYLACETAMIDE (13 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of N-methylacetamide with photochemically-produced hydroxyl radicals is 5.20X10-12 cu cm/molecule-sec at 27 °C(1). This corresponds to an atmospheric half-life of about 3.1 days(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). N-Methylacetamide is not expected to undergo hydrolysis in the environment due to the slow rate of reaction for amide functional groups nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

Probable Routes of Human Exposure · 1 件

NIOSH (NOES Survey 1981-1983) has statistically estimated that 851 workers (187 of these are female) are potentially exposed to N-methylacetamide in the US(1). Occupational exposure to N-methylacetamide may occur through inhalation and dermal contact with this compound at workplaces where N-methylacetamide is produced or used(SRC).

安全データ

wgk
2
tsca
TSCA listed
rtecs
AC5960000
毒性
LD50 oral in rat: 5gm/kg
hs_code
29241900
risk_code
61
化審法
(2)-3072
hazard_code
T
safety_code
53-45
Hazard Classifications
Repr. 1B
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
79-16-3(Hazardous Substances Data)
Formulations/Preparations
USEPA/OPP Pesticide Code 067301; Trade Names: Coop turbex; Turbex, Onyxide.
General Manufacturing Information · 2 件

Acetamide, N-methyl-: ACTIVE

DIMETHYL SULFOXIDE, N-METHYL ACETAMIDE & PYRIDINE N-OXIDE WERE MOST EFFECTIVE AGENTS TESTED FOR INDUCING DIFFERENTIATION OF MURINE ERYTHROLEUKEMIA CELLS IN VITRO.

応用分野

用途医薬中間体

使用N-Methylacetamide is used as a chemical intermediate in the production of life science, agrochemicals, electronic materials and construction materials. It is also used as a solvent, in electrochemistry.

調製方法 · 2 件

Af-Methylacetamide has been prepared by reaction of methylamine with hot acetic acid (D'Alelio and Reid, 1937) and with acetic anhydride (Mauger and Soper, 1946). Other methods include heating iV,N-dimethylurea with acetic acid (US Patent, 1936) and reduction/hydrogenation of N-(hydroxymethyl)acetamide (US Patent, 1944).

純化方法Fractionally distil it under vacuum, then fractionally crystallise it twice from its melt. Likely impurities include acetic acid, methyl amine and H2O. For a detailed purification procedure, see Knecht and Kolthoff, Inorg Chem 1 195 1962. Although N-methylacetamide is commercially available it is often extensively contaminated with acetic acid, methylamine, water and an unidentified impurity. The recommended procedure is to synthesise it in the laboratory by direct reaction. The gaseous amine is passed into hot glacial acetic acid, to give a partially aqueous solution of methylammonium acetate which is heated to ca 130o to expel water. Chemical methods of purification such as extraction by pet ether, treatment with H2SO4, K2CO3 or CaO can be used but are more laborious. Tests for purity include the Karl Fischer titration for water; this can be applied directly. Acetic acid and methylamine can be detected polarographically. In addition to the above, purification of N-methylacetamide can be achieved by fractional freezing, including zone melting, repeated many times, or by vacuum distillation under reduced pressures. For details of zone melting techniques, see Knecht in Recommended Methods for Purification of Solvents and Tests for Impurities, Coetzee Ed. Pergamon Press 1982.[Beilstein 4 IV 176.]

上流・下流製品情報

上流原料

N,N-ジメチルアセトアミド

下流製品

チロフィバン1,4-ジシアノナフタレン7-ヒドロキシ-3-(フェニル)-4H-1-ベンゾピラン-4-オンN-(5-ブロモピリミジン-2-イル)-N-メチルアセトアミド2,3-Dimethyl-3H-quinazolin-4-oneAcetamide, N-methyl-N-2-pyridinyl-

補足説明

定義ChEBI: N-methylacetamide is a monocarboxylic acid amide that is the N-methyl derivative of acetamide. It has a role as a metabolite. It is a member of acetamides and a monocarboxylic acid amide. It is functionally related to an acetamide.