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Acetanilide

HCID 904
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Basic information

CAS
103-84-4
Standard SMILES
CC(=O)Nc1ccccc1
InChIKey
FZERHIULMFGESH-UHFFFAOYSA-N
Molecular formula
C8H9NO
Average molar mass
135.16 g/mol
Monoisotopic mass
135.06841391

Overview

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

Names & identifiers

Preferred name
Acetanilide
IUPAC
N-phenylacetamide
English name
Acetanilide
Molecular formula
C8H9NO
Molecular weight
135.16

Names & synonyms

acetanilideN-Phenylacetamide103-84-4AntifebrinN-AcetylanilineAcetanilidAcetamidobenzeneAcetanilAcetylanilinePhenalgeneAcetamide, N-phenyl-Acetylaminobenzene
Show more names
Acetanilide (Acetylaniline)Acetylanilide
Acetic acid anilideAcetoanilidePhenalginAniline, N-acetyl-USAF EK-3Benzenamine, N-acetyl-AcetanilidumAntifebrinum

Database identifiers

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

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
29.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
116

Experimental & physicochemical properties

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 · 3 items

Log Kow= 1.16

1.16

1.14

OdorODORLESS
TasteSLIGHTLY BURNING
Density · 3 items

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

1.2190 @ 15 °C

1.21 @ 20°C

Color/Form · 4 items

ORTHORHOMBIC PLATES OR SCALES FROM WATER

WHITE SHINING CRYSTALLINE SCALES

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 2 items

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 · 1 item

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]

Chemistry & industry

Pharmacology

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 · 6 items

.../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 · 5 items

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

Uses & manufacturing

Uses · 6 items

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]

Related reactions

196 records
New reaction record
HRID 35392 reaction equation
HRID 35392As reactantuspto-grants-1988_08
HRID 46430 reaction equation
HRID 46430As productuspto-grants-1979_11
HRID 54916 reaction equation
HRID 54916As reactantuspto-grants-1997_04
HRID 65164 reaction equation
HRID 65164As productuspto-grants-1986_09
HRID 89356 reaction equation
HRID 89356As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 95811 reaction equation
HRID 95811As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 97217 reaction equation
HRID 97217As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 105249 reaction equation
HRID 105249As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Page 1 of 25

Compound notes

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White, shining crystalline leaflets or white crystalline powder.

Colorless, glossy, crystalline material.

Solubility · 6 items

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 · 3 items

345 °F (NTP, 1992)

169 °C

337 °F; 169 °C (OPEN CUP)

Physicochemical properties

Melting point
113 · 113-115 °C(lit.)
Boiling point
304 °C · 304 °C(lit.)
Density
1 · 1,121 g/cm3
bulk density
370 kg/m3 · 370kg/m3
vapor density
4.65 · 4.65 (vs air)
vapor pressure
1 mm · 1 mm Hg ( 114 °C)
refractive index
1.57 · 1.5700 (estimate)
Flash point
173 °C · 173 °C
storage temp.
30 °C · Store below +30°C.
solubility
Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether.
form
Powder
pka
0.5 · 0.5(at 25℃)
color
Off-white to beige to grayish-blue
PH
5 · 5-7 (10g/l, H2O, 25℃)
Water Solubility
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℃)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
Cosmetics Ingredients Functions
FRAGRANCEPERFUMING
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
CAS DataBase Reference
103 · 103-84-4(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
86 R356CC · SP86R356CC
NIST Chemistry Reference
Acetamide, N-phenyl-(103-84-4)
EPA Substance Registry System
Acetanilide (103-84-4)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Danger
Hazard statements
302 · H302-H315-H319-H361-H370-H372-H336-H402
Precautionary statements
501 · P501-P273-P260-P270-P202-P201-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22-36/37/38
Safety Statements
22 · 22-26-36
WGK Germany
1 · 1
RTECS
7350000 · AD7350000
Autoignition Temperature
540 °C · 540 °C
TSCA
TSCA listed
HS Code
29242995 · 29242995
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Hazardous Substances Data
103 · 103-84-4(Hazardous Substances Data)
Toxicity
50 intragastric · LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
Reactive Group
Amides and Imides
Reactivity Profile · 1 item

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 · 3 items

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 · 2 items

Acute Tox. 4 (99.9%)

Acute toxicity (Oral) - Category 4

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

Safety & protection

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

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 item

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 · 2 items

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) · 3 items

2.4 [mg/m3]

26 [mg/m3]

160 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Interactions · 5 items

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 · 3 items

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 · 1 item

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 · 5 items

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 · 1 item

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 · 1 item

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 · 1 item

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 · 1 item

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 · 5 items

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 · 1 item

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.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
AD7350000
hs_code
29242995
Toxicity
LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
risk_code
22-36/37/38
Signal word
Danger
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn
safety_code
22-26-36
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H361-H370-H372-H336-H402
Hazard Classifications
Acute Tox. 4 Oral
Autoignition Temperature
540 °C
Precautionary statements
P501-P273-P260-P270-P202-P201-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405
Hazardous Substances Data
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 · 3 items

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 · 3 items

Fragrance Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Cosmetics -> Stabilizing

General Manufacturing Information · 4 items

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.

Applications · 3 items

HistoryThe 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.

UsesAcetanilide is used as an intermediate in the synthesis of rubber accelerator, dyes and camphor. It is also used in the synthesis of penicillin and other pharmaceutical products. It is involved in the preparation of 4-acetamidobenzenesulfonyl chloride, which is an intermediate during the synthesis of sulfa drugs. Further, it is employed as a experimental photographic developer. In addition to this, it is used to stabilize cellulose ester varnishes.

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

Preparation methods · 1 item

PreparationAcetanilide 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).

Upstream & downstream products

Upstream raw materials

2-BenzoylacetanilideDistillatorAnilineAcetic acidBenzoic acid, 2-(acetylamino)-4-methyl- (9CI)

Downstream products

SulfasalazineSulfaquinoxalineDisperse Blue 301AsulamDoxycycline hydrochloride3-EthoxyanilineMethyl 4-(4-(bis(2-hydroxyethyl)amino)phenyl)butyrateSulfanilamide2-[(4-Aminophenyl)sulfonyl]ethyl hydrogen sulfateFast Yellow G4'-Aminoacetanilide4-Aminoacetophenone4-Amino-3-nitrophenol4-(4-Aminophenyl)butyric acidMethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butyrate9,9-Bis(4-aminophenyl)fluorene2-Morpholin-4-yl-1,3-thiazol-4(5H)-one4-(4-Iodo-phenyl)-4-oxo-butyric acidMethoxymethyldiphenylamine
Additional notes · 1 item

DefinitionChEBI: 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.