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カルバミン酸メチル

Methyl Carbamate

HCID 11722
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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
598-55-0
標準SMILES
COC(N)=O
InChIKey
GTCAXTIRRLKXRU-UHFFFAOYSA-N
分子式
C2H5NO2
平均分子量
75.07 g/mol
単同位体質量
75.0320284

概要

Methyl Carbamate can cause cancer according to The National Toxicology Program.

名称と識別子

優先名称
Methyl Carbamate
IUPAC
methyl carbamate
現地名
カルバミン酸メチル
英語名
Methyl carbamate
分子式
C2H5NO2
分子量
75.07

名称と別名

METHYL CARBAMATE598-55-0UrethylaneMethylcarbamateMethylurethanMethylurethaneCarbamic acid, methyl esterMethylkarbamatCarbamic acid methyl esterNCI-C55594Methylester kyseliny karbaminoveDTXSID8020834
名称をさらに表示
カルバミン酸メチルウレチランメチル=カルバマートカルバミド酸メチルメチルカルバミン酸塩カルバミン酸メチル, 99%MCMMECBCWS5MCMTC(?)-GCp55-gammap85-alphaurethylan
9WFX634X2TDTXCID60834NSC-3054CHEBI:76606RefChem:157812209-939-2CCRIS 885methylcarbamat

データベース識別子

CAS
598-55-0
PubChem CID
11722
DTXSID
DTXSID8020834
ChEMBL
CHEMBL1085707
ChEBI
CHEBI:76606
UNII
9WFX634X2T
EC Number
209-939-2
Nikkaji
J1.651I

物性

構造計算による物性補完中

XLogP
-0.7
極性表面積
52.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
5
形式電荷
0
複雑度
42.9

実験および物理化学的性質

Chemical ClassesOther Classes -> Carbamic Acid Esters
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

log Kow = -0.66

-0.64

Density · 2 件

1.1361 at 133 °F (NTP, 1992) - Denser than water; will sink

1.1361 g/cu cm at 56 °C

Color/Form · 2 件

WHITE CRYSTALS

NEEDLES

Solubility · 4 件

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)

SOL IN WATER: 217 PARTS IN 100 @ 11 °C

SOL IN ETHANOL: 73 PARTS IN 100 @ 15 °C; SOL IN ETHER

In water, 6.91X10+5 mg/l at 15.5 °C

Boiling Point · 2 件

351 °F at 760 mmHg (NTP, 1992)

177 °C

DecompositionWhen heated to decomposition it emits toxic fumes of NOx.
Melting Point · 2 件

129 °F (NTP, 1992)

52-54 °C

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 · 5 件

This chemical does not meet GHS hazard criteria for 0.1% (1 of 758) of reports.

Warning

H315 (65.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 758 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 5 件

Chemical: Carbamic acid, methyl ester

Hazard Traits - Carcinogenicity

Carbamic acid, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbamic acid, methyl ester 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)

REACH registered substance: Methyl carbamate (EC: 209-939-2)

Carbamic acid, methyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Overexposure to this compound may cause narcosis.
Hazards SummaryHigh levels of exposure may lead to narcosis; [CAMEO] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline]
Reactive GroupCarbamates

化学と産業

薬理情報

Absorption, Distribution and Excretion · 2 件

RATS INJECTED IP WITH METHYL CARBAMATE...EXCRETED...CARBAMATE...IN URINE...

DNA BINDING OF...(14)C-METHYL CARBAMATE LABELED IN METHYL GROUP HAS BEEN INVESTIGATED IN MOUSE LIVER & KIDNEY. ... INCORP OF (3)H-METHYL CARBAMATE INTO LIVER-CELL RNA HAS BEEN EXAMINED IN MICE...

用途と製造

Uses · 4 件

Used to make dimethylol methyl carbamate-based resins and pharmaceuticals; Also used in the textile industry as a fabric finish for polyester/cotton blends; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

USED IN EUROPE AS PHARMACEUTICAL INTERMEDIATE

An intermediate in the manufacture of dimethylol methyl carbamate-based resins, which are used in the textile industry as durable-press fabric finishes for polyester/cotton blends.

U.S. Production · 2 件

2023: 1,000,000 - <5,000,000 lb

(1975) PROBABLY GREATER THAN 9.1X10+5 GRAMS

Consumption PatternsPROBABLY 100% AS A CHEM INT FOR DIMETHYLOL METHYL CARBAMATE-BASED RESINS AS A DURABLE-PRESS FABRIC FINISH (1976)
Industry UsesAdhesion/cohesion promoter
Methods of Manufacturing · 2 件

FROM SILVER OR MERCURICYANATE WITH H2S & METHANOL: BIRKENBACH, KOLB, BER 68, 901 (1953). FROM UREA & METHANOL: GERMAN PATENT 753,127 (1940 TO IG FARBENIND).

IT CAN...BE PREPD BY REACTION OF AMMONIA WITH METHYL CHLOROFORMATE ... & THIS METHOD IS BELIEVED TO HAVE BEEN USED COMMERCIALLY.

General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing

Carbamic acid, methyl ester: ACTIVE

応用分野

関連反応

67 件
反応記録を作成
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HRID 84453 の反応式
HRID 84453反応物としてuspto-grants-2014_09
HRID 119374 の反応式
HRID 119374反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 202182 の反応式
HRID 202182反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 306493 の反応式
HRID 306493反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 417406 の反応式
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1 / 9 ページ

化合物ノート

読み込み中…

このページの内容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
その他の操作
ノートを作成反応を作成見積依頼を出す
Vapor Pressure
0.56 [mmHg]
Food Contact SubstancesFCS -> FDA Cumulative Estimated Daily Intake (CEDI)
Refractive IndexINDEX OF REFRACTION: 1.4125 @ 56 °C/D

物理化学的性質

融点
56 · 56-58 °C (lit.)
沸点
176 · 176-177 °C (lit.)
比重(密度)
1 · 1,14 g/cm3
屈折率
1.4125 · 1.4125
闪点
93 °C · 93 °C
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
700 g/L · 700g/L(20℃)
酸解離定数(Pka)
13.37 · 13.37±0.50(Predicted)
外見
結晶の付着
色
白い
PH
6 · 6-8 (50g/l, H2O, 20℃)
水溶解度
700 g/L · 700g/L(20℃)
Merck
14 · 14,6036
Specific Activity
11.2 · 11.2-16.8nmol/min·mg
BRN
635779 · 635779
Henry's Law Constant
2.5 · 2.5×102 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)
InChIKey
GTCAXTIRRLKXRU-UHFFFAOYSA-N
SMILES
COC(N)=O
CAS データベース
598 · 598-55-0(CAS DataBase Reference)
NISTの化学物質情報
Carbamic acid, methyl ester(598-55-0)
EPAの化学物質情報
Methyl carbamate (598-55-0)

化学的性質

化学的特性Methyl carbamate is a white, adhesive crystal. It is highly soluble in water, as well as in ethanol, acetone, and other organic solvents.

Special ReportsDHHS/NTP; Toxicology & Carcinogenesis Studies of Methyl Carbamate in F344/N Rats and B6C3F1 Mice Technical Report Series No. 328 (1987) NIH Publication No. 88-2584
Reactivity Profile · 1 件

METHYL CARBAMATE is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesSkin Irrit. 2 (65.4%)
Hazardous Reactivities and Incompatibilities · 1 件

This intermediate /N-carbomethoxymethylimino phosphoryl chloride/ (or its ethyl homolog), produced during prepn of phosphoryl dichloride isocyanate from interaction of phosphorus pentachloride & methyl (or ethyl) carbamate, is unstable. Its decomposition to the required product may be violent or explosive unless moderated by the presence of a halogenated solvent.

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

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.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

毒性情報

Interactions · 1 件

Male CF-1 mice were treated with urethane (0, 0.5, 1.0, 1.5, and 2 g/kg; ip) and 18 hr later hepatic metallothionein concentrations were determined with the cadmium hemoglobin radioassay. Urethane (1 g/kg and higher) significantly increase hepatic metallothionein levels, resulting in a 14 fold increase after 2 g/kg. Time course experiments indicated that metallothionein levels were increased significantly at 6 hr after administration of urethane (1.5 g/kg) and reached a maximum between 12 and 24 hr. Gel filtration, anion exchange chromatography, and UV spectral analysis were used to characterize the protein induced by urethane. Pretreatment with actinomycin-D prevented induction of metallothionein by urethane. Administration of equimolar dosages (20 mmol/kg) of urethane, N-hydroxyurethane, and methyl carbamate indicated that urethane and N-hydroxyurethane induce metallothionein but that methyl carbamate does not. Metallothionein induction was also not observed with (pentobarbital and phenobarbital). Urethane induces hepatic metallothionein but this effect is not related to its anesthetic action, nor is it a common property of all carbamates.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a measured log Kow of -0.66(2) and a recommended regression-derived equation(3), indicates that methyl carbamate is expected to have very high mobility in soil(SRC). However, methyl carbamate was determined to adsorb onto the clay mineral montmorillonite(4). Volatilization of methyl carbamate will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Hydrolysis of methyl carbamate in moist soils may be catalyzed by adsorption to Na+, Mg2+, Al3+, and Cu2+ montmorillonites(4,SRC). Biodegradation of methyl carbamate in soil may be important(SRC), based on its biodegradation in river and seawater(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a measured log Kow of -0.66(2) and a recommended regression-derived equation(3), indicates that methyl carbamate is not expected to adsorb to suspended solids and sediment in water(SRC). Methyl carbamate is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 0.19(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Methyl carbamate was degraded 19 and 18% in river and seawater, respectively, over a three day period(6). Purely aliphatic carbamates are expected to be resistant to hydrolysis under environmental conditions(7); hydrolysis half-lives of 3300 and 330 years at pH values of 7 and 8, respectively, were estimated for methyl carbamate(8,SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl carbamate, which has an estimated vapor pressure of 0.56 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl carbamate 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 about 4.8 days(3,SRC).

Food Survey Values · 1 件

Methyl carbamate was detected in trace amounts in red and white wines, sherry, whisky, and Armagnac(1). Methyl carbamate was detected in fruit brandy from France and Austria at an average concentration of 28 and 9 ug/kg, respectively(1). Methyl carbamate was detected in various breads, light toast, and dark toast at an average concentration of 3.0, 2.2, and 2.7 ug/kg, respectively(1). Trace levels, 1 to 4 ug/kg, of methyl carbamate were detected in various yogurt samples(1). Soy sauce samples contained minute amounts, 0.1 to 1.1 ug/kg, of methyl carbamate(1).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=598-55-0]

Soil Adsorption/Mobility · 1 件

The Koc of methyl carbamate is estimated as approximately 10(SRC), using a measured log Kow of -0.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that methyl carbamate is expected to have very high mobility in soil(SRC). Methyl carbamate adsorbs on Na+, Mg2+, Al3+, and Cu2+ montmorillonites which catalyze the hydrolysis of methyl carbamate when equilibrated at room temperature and 100% relative humidity(4).

Natural Pollution SourcesMETHYL CARBAMATE HAS BEEN ISOLATED FROM 4 SALSOLA SPECIES...
Artificial Pollution SourcesMethyl carbamate's production and use as an intermediate in the manufacture of dimethylol methyl carbamate-based resins(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationMethyl carbamate, present at a concentration of 100 ppm, was degraded 19 and 18% after three days cultivation in water from the Mino River and Akashi Beach, Japan, respectively(1).
Carcinogen Classification · 6 件

Methyl carbamate

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 12: (1976) Some Carbamates, Thiocarbamates and Carbazides

1987

1987

Methyl Carbamate

Environmental Bioconcentration · 1 件

An estimated BCF value of 0.19 was calculated for methyl carbamate(SRC), using a measured log Kow of -0.66(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for methyl carbamate is estimated as 4.0X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that methyl carbamate will be essentially nonvolatile from water surfaces(2,SRC). Methyl carbamate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC).

安全データ

wgk
3
tsca
TSCA listed
rtecs
FC2450000
hs_code
29241900
risk_code
36-40-61
hazard_code
Xn,T
safety_code
26-36/37-36-22-45-53
Hazard Classifications
Carc. 2Eye Irrit. 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
598-55-0(Hazardous Substances Data)
· 3 件

用途有機合成原料。

使用Methyl carbamate was used in the synthesis of protected aminocyclopropanes.

一般的な説明Methyl carbamate appears as white to Almost white powder to crystal. It an intermediate in the manufacture of dimethylol methyl carbamate-based resins, which are used in the textile industry as durable-press fabric finishes for polyester/cotton blends.

調製方法

純化方法Crystallise the carbamate from *benzene or distil it. [Beilstein 3 H 21.]

上流・下流製品情報

上流原料

尿素メチルクロロホルマートアンモニア

下流製品

METHYL PENT-4-YN-2-YLCARBAMATEアシュラムセフォニシドグリメピリドピコリン酸 メチル2-ブロモ-1-(3-ブロモフェニル)エタノンメタノール

補足説明

定義ChEBI: Methyl carbamate is a carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.