N-메틸아세트아마이드

N-메틸아세트아마이드 · 메틸아세타마이드 · NMA · Methylacetamide · CH3CONHCH3 · dpgs · X 44 · N-MethylacetaM

식별자 및 물리적 특성

CAS No.	79-16-3
분자식	C3H7NO
평균 분자량	73.09 g/mol
단동위원소 질량	73.05276384 g/mol
SMILES	CNC(C)=O
InChIKey	OHLUUHNLEMFGTQ-UHFFFAOYSA-N
PubChem CID	6582
ChEMBL	CHEMBL11544
ChEBI	CHEBI:87321
EC No.	201-182-6
DTXSID	DTXSID0047167
현지명	N-메틸아세트아마이드

화학 및 물리적 성질

XLogP	-1.1
극성 표면적	29.1
수소 결합 공여자 수	1
수소 결합 수용자 수	1
회전 가능 결합 수	0
무거운 원자 수	5
형식 전하	0
복잡도	42.2
물질 분류	Nitrogen Compounds -> Other Nitrogen Compounds
SpringerMaterials Properties	15N nuclear magnetic resonance spectrum
LogP(분배 계수)	log Kow = -1.05
밀도	0.9371 @ 25 °C/4 °C0.957 g/mL at 25 °C (lit.)
Viscosity	3.65 centipose (30 °C)3.23 centipose (35 °C)3.012 centipose (40 °C)
Color/Form	NEEDLES
용해도	SOL IN CHLOROFORMSoluble in alcohol, ether, acetone, benzeneIn water, 1X10+6 mg/l @ 20 °C에탄올, 에테르, 아세톤, 물, 클로로포름, 벤젠과 혼합 가능
인화점	108 °C227 °F
끓는 점	205 °C204-206 °C (lit.)
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
녹는점	28 °C26-28 °C (lit.)
증기압	0.44 [mmHg]0.44 mm Hg at 23 °C.12-3680Pa at 15-113℃
굴절률	n20/D 1.433(lit.)
저장 조건	Inert atmosphere,Room Temperature
pKa(산도 계수)	16.61±0.46(Predicted)
물리적 상태	고체
색상	무색
pH	7 (H2O)
폭발한계	3.2-18.1%(V)
용해도	녹는
BRN	1071255
헨리 상수	2.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
유전율	178.90000000000001
안정성	안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
InChI	1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)
InChIKey	OHLUUHNLEMFGTQ-UHFFFAOYSA-N
SMILES	CNC(C)=O
LogP(분배 계수)	-1.05--0.7 at 25℃
표면장력	34.13mN/m at 293.15K
NIST	Acetamide, N-methyl-(79-16-3)
EPA	N-Methylacetamide (79-16-3)

화학적 성질

colourless liquid or solid. Soluble in water, ethanol, benzene, ether, chloroform, insoluble in petroleum ether.

안전 및 규제

GHS 분류	DangerH360D ***: May damage the unborn child [Danger Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)H360 (97.5%): May damage fertility or the unborn child [Danger Reproductive toxicity]
규제 정보	Chemical: Acetamide, N-methyl-Hazard Traits - Reproductive ToxicityStatus: Active Update: 02-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/26228Substance: N-methylacetamideMethylacetamide: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보	IMAP assessments - Acetamide, N-methyl-: Human health tier II assessment
유해성 요약	Mice that died 24-48 hours following administration exhibited toxic hepatitis, necrosis of pancreas, and testicular atrophyCauses hyperglycemia in ratsA 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 Products	When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Hazard Classes and Categories	Repr. 1B (97.5%)Reproductive toxicity - category 1BReproductive toxicity - Category 2
Critical Temperature and Pressure	Critical temperature: 417 °C
처리 방법	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.
상호 작용	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.
환경 거동	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).
유해 작용	Occupational 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	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	/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 Sources	N-Methylacetamide's production and use as a solvent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation	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	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	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	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	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	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).
수질 위해 등급(WGK)	2
TSCA 등재 상태	TSCA listed
RTECS 번호	AC5960000
독성	LD50 oral in rat: 5gm/kg
관세 코드	29241900
위험 문구(R)	61
위험 표시	T
안전 문구(S)	53-45
기존화학 물질	KE-23402
위험 등급	Repr. 1B
저장 분류	6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터	79-16-3(Hazardous Substances Data)
중점관리물질 필터링	별표2-17

용도

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.

제조 및 합성 방법

생산 방법

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).