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아세트아닐리드

Acetanilide

HCID 904
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
103-84-4
표준 SMILES
CC(=O)Nc1ccccc1
InChIKey
FZERHIULMFGESH-UHFFFAOYSA-N
분자식
C8H9NO
평균 분자량
135.16 g/mol
단동위원소 질량
135.06841391

개요

Acetanilide is a white to gray solid. (NTP, 1992)

이름 및 식별자

우선 이름
Acetanilide
IUPAC
N-phenylacetamide
현지명
아세트아닐리드
영어명
Acetanilide
분자식
C8H9NO
분자량
135.16

이름 및 동의어

acetanilideN-Phenylacetamide103-84-4AntifebrinN-AcetylanilineAcetanilidAcetamidobenzeneAcetanilAcetylanilinePhenalgeneAcetamide, N-phenyl-Acetylaminobenzene
이름 더 보기
아세트아닐리드N-페닐ACETICACIDANILIDE아세트산아닐리드아세트아닐아세트아미도벤젠아세틸아미노벤젠안티페브린페날긴페날진아세트아닐라이드N-아세틸아닐린N-페닐아세트아마이드아세토아닐리드아세트 산 아닐리드아세틸 아미노벤젠아세틸아닐린Acetanilide (Acetylaniline)Acetylanilide
Acetic acid anilideAcetoanilidePhenalginAniline, N-acetyl-USAF EK-3Benzenamine, N-acetyl-AcetanilidumAntifebrinum

데이터베이스 식별자

CAS
103-84-4、55576-55-1
PubChem CID
904
DTXSID
DTXSID2022543
ChEMBL
CHEMBL269644
ChEBI
CHEBI:28884
UNII
SP86R356CC
EC Number
203-150-7、695-031-5
Nikkaji
J4.023A

물성

구조 계산 물성

XLogP
1.2
극성 표면적
29.1 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
10
형식 전하
0
복잡도
116

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
DrugsDEA NFLIS-Drug Category -> Analgesics
CosmeticsStabilizing
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Acetanilide) -> IFRA transparency List
LogP · 3건

Log Kow= 1.16

1.16

1.14

OdorODORLESS
TasteSLIGHTLY BURNING
Density · 3건

1.219 at 59 °F (NTP, 1992) - Denser than water; will sink

1.2190 @ 15 °C

1.21 @ 20°C

Color/Form · 4건

ORTHORHOMBIC PLATES OR SCALES FROM WATER

WHITE SHINING CRYSTALLINE SCALES

White, shining crystalline leaflets or white crystalline powder.

Colorless, glossy, crystalline material.

Solubility

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1686) of reports.

Warning

H302 (99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1686 reports by companies from 15 notifications to the ECHA C&L Inventory.

Warning

유해성 정보

Regulatory Information · 2건

Chemical: Acetamide, N-phenyl-

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

Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include contact dermatitis and eczematous skin eruptions; anemia and cyanosis.
Hazards Summary · 1건

Heavy or repeated exposure may produce methemoglobinemia, CNS depression, circulatory collapse, and contact dermatitis in humans; Causes methemoglobinemia in high-dose animal studies; Mutagenic in micronucleus assay with mice; Emergency treatment: Phenacetin; Phenacetin was used as a pain-relieving drug, but has not been available in the US since 1983. Can cause methemoglobinemia after ingestion >1 gram/day; Phenacetin can cause renal papillary necrosis following ingestion of large doses for years; [HSDB] An irritant; May cause contact dermatitis, eczematous skin eruptions, anemia, and cyanosis; [CAMEO] An allergen; May cause eczematous dermatitis, methemoglobinemia, and cyanosis; [EPA OHM/TADS] Causes acute tubular necrosis and methemoglobinemia in oral toxic-dose exposures in humans; [RTECS] An irritant; May cause serious eye injury; Harmful if swallowed; [Aldrich MSDS]

Reactive GroupAmides and Imides

화학 및 산업

약리 정보

Biological Half-LifeT/2 OF ACETANILID MEASURED IN POPULATIONS OF YOUNG (AGED 20-35 YR) & ELDERLY (AGED OVER 65 YR) PEOPLE (TOTAL= 93). T/2 WERE SIGNIFICANTLY LONGER IN THE ELDERLY.
Metabolism/Metabolites · 6건

.../RESEARCHERS/ FOUND THAT STARVATION DECREASED RATE OF METABOLISM OF...ACETANILIDE. ...STARVATION REDUCED OXIDATIVE PATHWAYS OF MALE RATS...

STRAIN DIFFERENCES /WITHIN THE SAME SPECIES/ WERE...NOTED IN ACETANILIDE...METABOLISM.

HEPATIC MICROSOMES FROM RABBITS WITH OBSTRUCTIVE JAUNDICE SHOW IMPAIRED METABOLISM OF ACETANILIDE...

2 NEW URINARY METABOLITES OF ACETANILIDE IN RATS THAT HAVE BEEN IDENTIFIED AS N-ACETYL-S-(5-ACETAMIDO-2-HYDROXYPHENYL)CYSTEINE & N-ACETYL-S-(3-ACETAMIDOPHENYL)CYSTEINE MAY HAVE BEEN FORMED VIA AN INTERMEDIATE EPOXIDE.

For more Metabolism/Metabolites (Complete) data for ACETANILIDE (20 total), please visit the HSDB record page.

Acetanilide has known human metabolites that include N-Hydroxy-N-phenylacetamide and acetaminophen.

Absorption, Distribution and Excretion · 5건

IT IS READILY EXCRETED IN THE URINE AS SULFATE OR GLUCURONATE CONJUGATE OF THE PHENOL /N-ACETYL-P-AMINOPHENOL/.

36% OF ACETANILIDE DISSOLVED IN 0.1 N HCL (PKA 0.3) WAS ABSORBED FROM RAT STOMACH IN ONE HOUR. /FROM TABLE/

...GREATER THAN 99.9% OF ACETANILIDE REMAINS UN-IONIZED @ BODY PH, FACILITATING ABSORPTION FROM BLOOD TO CEREBROSPINAL FLUID. THE BLOOD-CEREBROSPINAL FLUID PERMEABILITY COEFFICIENT IS 0.039/MIN. /FROM TABLE/

.../ACETANILID IS/ READILY ABSORBED FROM GASTROINTESTINAL TRACT.

For more Absorption, Distribution and Excretion (Complete) data for ACETANILIDE (14 total), please visit the HSDB record page.

Cellular LocationsMembrane

용도 및 제조

Uses · 6건

Used in the manufacture of camphor, penicillin, sulfa drugs, and dyes; Also used as a stabilizer for hydrogen peroxide, an additive to cellulose ester varnishes, a rubber accelerator, an antiseptic, a plasticizer, and a veterinary analgesic and antipyretic agent; [HSDB]

관련 반응

196건
반응 기록 만들기
HRID 35392 반응식
HRID 35392반응물로uspto-grants-1988_08
HRID 46430 반응식
HRID 46430생성물로uspto-grants-1979_11
HRID 54916 반응식
HRID 54916반응물로uspto-grants-1997_04
HRID 65164 반응식
HRID 65164생성물로uspto-grants-1986_09
HRID 89356 반응식
HRID 89356생성물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 95811 반응식
HRID 95811생성물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 97217 반응식
HRID 97217반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 105249 반응식
HRID 105249반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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새 노트새 반응견적 요청하기
· 6건

less than 1 mg/mL at 72 °F (NTP, 1992)

1 G SOL IN 185 ML WATER, 3.4 ML ALC, 20 ML BOILING WATER, 3 ML METHANOL, 4 ML ACETONE, 0.6 ML BOILING ALCOHOL, IN 3.7 ML CHLOROFORM, 5 ML GLYCEROL, 8 ML DIOXANE, 47 ML BENZENE, 18 ML ETHER; VERY SPARINGLY SOL IN PETROLEUM ETHER; CHLORAL HYDRATE INCREASES SOLUBILITY IN WATER

SOL IN TOLUENE; VERY SOL IN HOT TOLUENE, IN CARBON TETRACHLORIDE

Water solubility= 6.93X10+3 mg/l at 25 °C

Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether.

6.39 mg/mL at 25 °C

Flash Point · 3건

345 °F (NTP, 1992)

169 °C

337 °F; 169 °C (OPEN CUP)

물리화학적 성질

녹는점
113 · 113-115 °C(lit.)
끓는 점
304 °C · 304 °C(lit.)
밀도
1 · 1,121 g/cm3
증기 밀도
4.65 · 4.65 (vs air)
증기압
1 mm · 1 mm Hg ( 114 °C)
굴절률
1.57 · 1.5700 (estimate)
인화점
173 °C · 173 °C
저장 조건
30 °C · Store below +30°C.
용해도
물에 약간 용해됨; 에탄올과 아세톤에 매우 잘 녹습니다. 에틸 에테르에 용해됩니다.
물리적 상태
가루
산도 계수 (pKa)
0.5 · 0.5(at 25℃)
색상
미색에서 베이지색, 회청색까지
수소이온지수(pH)
5 · 5-7 (10g/l, H2O, 25℃)
수용성
5 g/L · 5 g/L (25 ºC)
Merck
14 · 14,50
BRN
606468 · 606468
Henry's Law Constant
4.7 · 4.7×102 mol/(m3Pa) at 25℃, Yaws (2003)
Dielectric constant
2.9 · 2.9(22.0℃)
안정성
안정적인. 타기 쉬운. 강한 산화제, 부식제, 알칼리와 호환되지 않습니다.
화장품 원료 기능
향기향수
InChI
1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
InChIKey
FZERHIULMFGESH-UHFFFAOYSA-N
SMILES
CC(=O)Nc1ccccc1
LogP
1.16 · 1.160
NIST
Acetamide, N-phenyl-(103-84-4)
EPA
Acetanilide (103-84-4)
화학적 성질 · 1건

Acetanilide, also known as Nphenylacetamide, acetanil, or acetanilide is a white to gray solid with molecular formula CH3CONHC6H5. It is an odorless colorless, glossy, crystalline powder or flakes. Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties and was quickly introduced into medical practice (Weast, 1981; Gnanasambandan et al., 2014). Later, it was established that in the human body it is mostly metabolized to paracetamol, this compound being responsible for the analgesic and antipyretic properties of acetanilide (Bertolini et al., 2006; Gnanasambandan et al., 2014). In addition, it was discovered that it has unacceptable toxic effects, so that acetanilide is no longer used as a drug. Acetanilide is mainly used as an intermediates in the synthesis of pharmaceuticals and dyes, as an additive for hydrogen peroxide and cellulose ester varnishes, and as a plasticizer in polymer industry as well as accelerator in the rubber industry.

Reactivity Profile · 1건

ACETANILIDE is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Air and Water ReactionsThis compound is sensitive to prolonged exposure to air (NTP, 1992). Water insoluble.
NFPA Hazard Classification · 3건

3 - Materials that, under emergency conditions, can cause serious or permanent injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and Categories · 2건

Acute Tox. 4 (99.9%)

Acute toxicity (Oral) - Category 4

Hazardous Reactivities and IncompatibilitiesSEE ANILINE...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.

안전 및 보호

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

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 · 1건

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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 · 2건

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.

Incineration: Incineration at 1000 °C followed by treatment of the off-gas has been recommended. Landfill burial has also been suggested. But, in light of the generation of more toxic, persistent products, this mode of disposal does not seem desirable.

Protective Action Criteria (PAC) · 3건

2.4 [mg/m3]

26 [mg/m3]

160 [mg/m3]

Personal Protective Equipment (PPE) · 1건

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

독성 정보

Interactions · 5건

THIRTY-MOLAR EXCESS OF ACETANILIDE REDUCED CARCINOGENICITY OF N-2-FLUORENYLACETAMIDE ON LIVER & SEVERAL OTHER TARGET ORGANS IN SEVERAL SPECIES.

/ACETANILID/ WILL...POTENTIATE ANALGESIC EFFECTS OF OPIATES.

ENHANCING EFFECT OF METAPYRONE UPON THE P-HYDROXYLATION OF ACETANILIDE HAS BEEN CONFIRMED.

ACUTE EFFECT OF ORAL ADMIN OF BENZENE ON LIVER MICROSOMAL DRUG ENZYMES AND LIPID PEROXIDATION WAS INVESTIGATED IN RATS. INCR IN HYDROXYLATION OF ACETANILIDE WAS OBSERVED.

For more Interactions (Complete) data for ACETANILIDE (11 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), a measured Koc value of 27(2,SRC), indicates that acetanilide will have very high mobility in soil(SRC). Volatilization of acetanilide from moist soil surfaces is not expected to be important(SRC) given an estimated Henry's Law constant of 6.2X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of acetanilide from dry soil surfaces may not exist(SRC) based on the extrapolated vapor pressure of 1.2X10-3 mm Hg(4,SRC). Limited data suggest that acetanilide may undergo microbial degradation in soil.

AQUATIC FATE: Based on a recommended classification scheme(1), a measured Koc value of 27(2,SRC),indicates that acetanilide is not expected to adsorb to suspended solids and sediment in water(SRC). Acetanilide is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 6.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(5), an estimated BCF value of 4.5(1,SRC), from an experimental log Kow(4,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Acetanilide should biodegrade rapidly in aquatic systems. Hydrolysis of acetanilide is not expected to be an environmentally important removal process in aquatic systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetanilide, which has an extrapolated vapor pressure of 1.2X10-3 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Vapor-phase acetanilide 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 1.3 days(3,SRC).

Adverse EffectsNephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.
Effluent ConcentrationsAcetanilide was detected in one wastewater sample from an undisclosed specialty chemicals manufacturing plant at a level of 0.2 ppm between Nov. 6, 1975 and Sept. 6, 1976(1).
Soil Adsorption/Mobility · 1건

The Koc of acetanilide is estimated as approximately 38(SRC), using an experimental log Kow of 1.16(1,SRC) and a regression-derived equation(2,SRC). A Koc of 27 was experimentally determined for acetanilide, using silt loam and sandy loam, with % organic matter ranging from 1.09-5.92 (Kom was converted to Koc by multiplying by 1.724), and pH ranging from 5.9-7.5(4). According to a recommended classification scheme(3), the estimated and measured Koc values suggest that acetanilide has very high mobility in soil(SRC).

Human Toxicity Excerpts · 5건

IT IS WELL KNOWN TO PRODUCE CYANOSIS IN SOME HUMANS WHEN TAKEN REPEATEDLY, POSSIBLY DUE TO FORMATION OF SULFHEMOGLOBIN. LARGE DOSES IN ACUTE POISONING PRODUCE METHEMOGLOBIN...

.../"COAL TAR ANALGETICS" INCL ACETANILID/ ARE DEPRESSANTS OF CNS. SYMPTOMS OF NAUSEA & VOMITING, VERTIGO & RINGING IN EARS...OCCUR WITH LARGE DOSES OR IN... SENSITIVE INDIVIDUALS WITH THERAPEUTIC DOSES. SWEATING MAY BE PROFUSE. LARGE DOSES LEAD TO MENTAL CONFUSION, MUSCULAR INCOORDINATION & COMA.

CIRCULATORY COLLAPSE, WITH COLD EXTREMITIES, PALENESS...FEEBLE RAPID PULSE & DYSPNEA, & COMA, WITH FIXED, SEMI-DILATED PUPILS, IS CHARACTERISTIC FINDING IN ACUTE ACETANILID POISONING.

IT MAY...CAUSE CONTACT DERMATITIS & INHALATION OR INGESTION MAY CAUSE AN ECZEMATOUS ERUPTION OF THE SKIN.

For more Human Toxicity Excerpts (Complete) data for ACETANILIDE (9 total), please visit the HSDB record page.

Artificial Pollution Sources · 1건

Acetanilide's production and use as an intermediate in drug and dye manufacture(1), a stabilizer for hydrogen peroxide(1) and cellulose esters(2), a plasticizer(2), and a rubber accelerator(3) may result in its release to the environment through various waste streams(SRC). Acetanilide has been found to be a thermal decomposition product of epoxy powder paint(4).

Environmental Biodegradation · 1건

Several tests indicate that acetanilide biodegrades rapidly under aerobic conditions(1-3). One screening test, based on COD measurements, using an activated sludge seed and an initial chemical concentration of 200 ppm, reported a 94% COD removal after 5 days(1). A screening test using an acclimated riverwater seed, based on BOD measurements, reported an 80% BODT after 8 days(2). A grab sample test from the Nile River, using an initial chemical concentration of 6-7 ppm, reported 100% degradation after 43 days incubation(3).

Environmental Bioconcentration · 1건

An estimated BCF value of 4.5 was calculated for acetanilide(SRC), using an experimental log Kow of 1.16(1,SRC) 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 · 1건

The Henry's Law constant for acetanilide is estimated as 6.2X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that acetanilide will be essentially nonvolatile from water surfaces(2,SRC). Acetanilide's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may not occur(SRC). The potential for volatilization of acetanilide from dry soil surfaces may not exist(SRC) based on the extrapolated vapor pressure of 1.2X10-3 mm Hg(3,SRC).

Non-Human Toxicity Excerpts · 5건

ACUTE TOXICITY...IS VERY LOW--RATS & MONKEYS TOLERATING DOSES OF 200-400 MG/KG ORALLY PER DAY FOR MANY WEEKS. WITH VERY LARGE DOSES...METHEMOGLOBIN & SOME HYPERPLASIA OF BONE MARROW CAN BE PRODUCED.

IN MOUSE, RAT, GUINEA PIG, AND RABBIT LIVER MICROSOMES GLUTATHIONE DEPLETION WAS NOT OBSERVED WITH ACETANILIDE.

At a single dose of 200 mg/kg by gavage, acetanilide oxidized hemoglobin to methemoglobin in dogs. /From table/

If a value of 100 is assigned to the sensitivity of the cat /with respect to methemoglobin formation/, then the sensitivities of other species are as follows for acetanilide: man, 56; dog, 29; rat, 5; rabbit, 0; and monkey, 0.

For more Non-Human Toxicity Excerpts (Complete) data for ACETANILIDE (6 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of acetanilide with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the aqueous-phase reaction with photochemically-produced hydroxyl radicals has been determined to be 5.2X10+9 L/mol-sec at pH 9(2). This corresponds to as aqueous half-life of approximately 154 days at an aqueous hydroxyl radical concentration of 1.0X10-17 mol/l(2). Acetanilide is not expected to undergo hydrolysis or direct photolysis in the environment due to the lack of functional groups to hydrolyze or absorb UV light.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
AD7350000
독성
LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
HS 번호
29242995
risk_code
22-36/37/38
hazard_code
Xn
safety_code
22-26-36
기존화학 물질
KE-28264
자연 발화 온도
540 °C
Hazard Classifications
Acute Tox. 4 Oral
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
103-84-4(Hazardous Substances Data)

Painting (Pigments, Binders, and Biocides) [Category: Paint]

MFR OF MEDICINALS, DYES; STABILIZER FOR HYDROGEN PEROXIDE; AS ADDN TO CELLULOSE ESTER VARNISHES

RUBBER ACCELERATOR

MFR OF INTERMEDIATES; IN SYNTHETIC CAMPHOR; PRECURSOR IN PENICILLIN MFR

Intermediate for sulfa drugs; hydrogen peroxide stabilizer; azo dye manufacture

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production(1986) No Data
Methods of Manufacturing · 3건

USUALLY PREPARED FROM ANILINE & ACETIC ACIDS: AI VOGEL, PRACTICAL ORGANIC CHEMISTRY, (LONDON, 3RD ED 1959), PAGE 577. FROM ANILINE & ACETYL CHLORIDE: GATTERMANN-WIELAND, PRAXIS DES ORGANISCHEN CHEMIKERS, (BERLIN, 40TH ED, 1961) PAGE 114.

FROM ANILINE, ACETONE & KETENE: HURD, ORG SYN, COLL VOL I, (NEW YORK, 2ND ED, 1941) PAGE 332.

Heating aniline with acetic anhydride.

Formulations/PreparationsGRADES: TECHNICAL; CP.
Use Classification · 3건

Fragrance Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Cosmetics -> Stabilizing

General Manufacturing Information · 4건

Acetamide, N-phenyl-: ACTIVE

INCOMPATIBILITIES: ...FERRIC SALTS (RED COLOR OR PRECIPITATE).

INCOMPATIBILITIES: ETHYL NITRATE, AMYL NITRITE, ACID SOLN OF NITRILES, ALKALIES (ANILINE LIBERATED), ALKALI BROMIDE & IODIDES IN AQ SOLN (INSOL COMPD FORMED); CHLORAL HYDRATE, PHENOL, RESORCINOL, THYMOL (THESE PRODUCE LIQ OR SOFT MASS ON TRITURATION)...

ACETANILID IS PARENT MEMBER OF /SO-CALLED COAL TAR ANALGESICS, PHENACETIN & ITS...METABOLITE ACETAMINOPHEN/... IT WAS INTRODUCED INTO MEDICINE IN 1886 UNDER NAME OF ANTIFEBRIN.../AFTER DISCOVERY OF/ ITS ANTIPYRETIC ACTION. ... PROVED TO BE EXCESSIVELY TOXIC, &...REPORTS OF POISONING...PROMPTED SEARCH FOR LESS TOXIC COMPD.

응용 분야 · 2건

역사The department of internal medicine at the University of Strassburg in the 1880s was noted for its investigations into intestinal worms. Adolf Kussmaul, the director, asked two young assistants, Arnold Cahn and Paul Hepp, to treat patients with naphthalene as it had been used elsewhere as an internal antiseptic. The young doctors were disappointed with the initial results, but Hepp persevered with the naphthalene treatment in a patient suffering from a variety of complaints besides worms. Surprisingly, the fever chart revealed a pronounced antipyretic effect from this treatment. This had not been observed before, but further investigation revealed that Hepp had wrongly been supplied by Kopp’s Pharmacy in Strassburg with acetanilide instead of naphthalene! Cahn and Hepp lost no time in publishing a report on their discovery of a new antipyretic. For many years after its discovery in 1886, Acetanilide was used as an alternative to aspirin (i.e. acetyl salicylate) - an analgesic (painkiller) and antipyretic (fever reducing) drug to relieve e.g. headache, menstrual pain, and rheumatic pain. Under the name “Acetanilide” it formerly appeared in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that Acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately causing damage to the liver and kidneys. Thus, Acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen (i.e. paracetamol), which is a metabolite of Acetanilide and whose use Axelrod and Brodie suggested in the same study.

일반 설명Acetanilide is a white to gray solid. (NTP, 1992)

제조 방법 · 1건

Acetanilide is prepared from aniline by acetylating it with acetic anhydride in presence of glacial acetic acid. Aniline reacts with acetic anhydride to form Acetanilide by nucleophilic substitution reaction and the reaction is called acetylation.In a 100 ml round bottom flask fitted with a reflux condensor place 5ml of aniline and 10 ml of 1:1 acetic acid and acetic anhydride mixture (5ml acetic acid and 5 ml acetic anhydride). Heat the mixture gently under reflux for 15-20 minutes on oil bath and then pour the contents while still hot with stirring into a 200ml beaker containing 100ml ice cold water. Stir the mixture vigorously to hydrolyse the excess acetic anhydride. After all the acetanilide has precipitated, collct it on buchner funnel and wash with cold water. Recrystallise the crude product from boiling water. If the product is excessively coloured add a pinch of animal charcoal to hot water and filter hot through glass wool/ cotton plug. Pure colourless crystals of acetanilide melts at 114°C (5-5.5g).

상·하류 제품 정보

상류 원료

2-벤조일아세트아닐리드Distillator아닐린아세트산(빙초산)벤조산,2-(아세틸아미노)-4-메틸-(9CI)

하류 제품

설파살라진설파퀴녹살린Disperse Blue 301AsulamDoxycycline hydrochloride3-에톡시아닐린메틸4-(4-(BIS(2-HYDROXYETHYL)AMINO)페닐)부티레이트설파닐아미드2-(4-아미노페닐술포닐)에틸 황산염료 옐로우 1p-아미노아세트아닐리드p-아미노아세트페논4-아미노-3-나이트로페놀4-(4-Aminophenyl)butyric acid메틸4-(4-(BIS(2-클로로에틸)아미노)페닐)부티레이트4,4′-(9-플루오레닐아이딘)다이아닐린2-Morpholin-4-yl-1,3-thiazol-4(5H)-one4-(4-Iodo-phenyl)-4-oxo-butyric acid2-메틸-4-메톡시디페닐아민
추가 설명 · 1건

정의ChEBI: Acetanilide is a member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group. It has a role as an analgesic. It is a member of acetamides and an anilide. It is functionally related to an acetic acid.