Acetanilide

Log Kow= 1.16

1.16

1.14

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

1.2190 @ 15 °C

1.21 @ 20°C

ORTHORHOMBIC PLATES OR SCALES FROM WATER

WHITE SHINING CRYSTALLINE SCALES

White, shining crystalline leaflets or white crystalline powder.

Colorless, glossy, crystalline material.

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

345 °F (NTP, 1992)

169 °C

337 °F; 169 °C (OPEN CUP)

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

Chemical: Acetamide, N-phenyl-

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

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]

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).

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.

Acute Tox. 4 (99.9%)

Acute toxicity (Oral) - Category 4

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.

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.

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.

2.4 [mg/m3]

26 [mg/m3]

160 [mg/m3]

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)

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.

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).

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).

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.

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).

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).

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).

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).

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.

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.

.../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.

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.

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]

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

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.

Fragrance Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Cosmetics -> Stabilizing

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.