Acetanilide

135.16

135.16

606468

203-150-7

SP86R356CC

757879|7636

DTXSID2022543

ORTHORHOMBIC PLATES OR SCALES FROM WATER|WHITE SHINING CRYSTALLINE SCALES|White, shining crystalline leaflets or white crystalline powder.|Colorless, glossy, crystalline material.

29242995

29.1

1.16

Off-white to beige to grayish-blue Powder

1.2190 g/cm³ @ Temp: 15 °C

114.3 °C

304 °C @ Press: 760 Torr

173 °C

1.5700 (estimate)

H2O: 5 g/L (25 ºC)

Store below +30°C.

1 mm Hg ( 114 °C)

4.65 (vs air)

Oral-Rat LD50: 800  mg/kg; Oral-Mouse LD50: 1210 mg/kg

Combustible in case of fire, high temperature and strong oxidant; burning and decomposition release toxic nitrogen oxide fumes

ODORLESS

SLIGHTLY BURNING

KB: 1X10-13 AT 28 °C|pKa = 0.50 at 25 °C (conjugate acid)

124.17 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|125 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

IT FORMS EUTECTIC MIXTURE WITH PHENOL, RESORCINOL, & THYMOL|VAPOR PRESSURE: 1 MM HG @ 114.0 °C

This compound is sensitive to prolonged exposure to air (NTP, 1992). Water insoluble.

Amides and Imides

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).

1004 °F (NTP, 1992)|985 + or - 10 °F.

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

1

22-36/37/38

22-26-36

AD7350000

Xn

Complete packaging, light loading and unloading; warehouse ventilated, away from open flame, high temperature, and stored separately from oxidant

Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.

P301 + P312 + P330

H302

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.

SEE ANILINE...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.

This chemical is combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 1620 companies from 11 notifications to the ECHA C&L Inventory.|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P281, P301+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P330, P337+P313, P403+P233, P405, and P501

Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

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)

| 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.

Acetanilide 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).

moderately toxic

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.

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).

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 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.

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).

26.92 L/kg|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).

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).

DRINKING WATER: Acetanilide was quantitatively detected in drinking water in Cincinnati, OH on Jan. 14, 1980(1).

...REACTION OF WORKERS WHO FILL BAGS OF ACETANILIDE. AFTER DUTY HR MOST...COMPLAINED OF CHEST PAIN, GIDDINESS, EPIGASTRIC PAIN & HIGHLY COLORED URINE. ...OCCASIONALLY THERE WAS TINGE OF CYANOSIS. HEMOGLOBIN VALUES...WERE BETWEEN 70 & 85%.|SYMPTOMS OF OCCUPATIONALLY CAUSED ACETANILIDE POISONING ARE PRESENTED WITH PARTICULAR EMPHASIS ON CYANOSIS, GIDDINESS & DELAYED ABSORPTION. TREATMENT AND PREVENTATIVE MEASURES ARE ALSO DESCRIBED.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 9000 workers (6100 of these are female) are potentially exposed to acetanilide in the US(1). Limited monitoring data indicate that non-occupational exposure can occur from the ingestion of contaminated drinking water. The most probable human exposure would be occupational exposure, which may occur through dermal contact at workplaces where acetanilide is produced or used(SRC).

IT IS PARTICULARLY EFFECTIVE AS AN ANALGESIC IN PAIN OF THE NEURALGIC TYPE...|MEDICATION (VET): ANALGESIC, ANTIPYRETIC AGENT

.../ACETANILID IS/ ESPECIALLY DANGEROUS IN ANEMIA, AFTER HEMORRHAGE AND DURING MENSTRUATION.|...ITS USE AS AN ANALGESIC /IS CONDEMNED/ BECAUSE SAFER & EQUALLY EFFECTIVE DRUGS ARE AVAILABLE.|...NECROSIS OF RENAL PAPILLAE & TERMINAL TUBULES HAS BEEN ASSOCIATED WITH EXCESSIVE DOSES OF DRUG MIXTURES CONTAINING ACETOPHENETIDIN WITH...ACETANILID...|...ACETANILID.../PRODUCES/ HEMOLYTIC ANEMIA IN INDIVIDUALS WITH GENETIC DEFICIENCY OF ERYTHROCYTIC GLUCOSE-6-PHOSPHATE DEHYDROGENASE. DARK SKINNED RACES HAVE HIGHER INCIDENCE THAN LIGHT SKINNED BUT DISEASE HAS NOT BEEN NOTED IN NORTH AMERICAN INDIANS OR ESKIMOS.|For more Drug Warnings (Complete) data for ACETANILIDE (6 total), please visit the HSDB record page.

/BETWEEN 4 & 5/: 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOONFUL & 1 OZ FOR A 70 KG PERSON (150 LB). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB).

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.

.../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.

T/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.

SYMPTOMS: Symptoms of exposure to this compound may include contact dermatitis and eczematous skin eruptions; anemia and cyanosis. ACUTE/CHRONIC HAZARDS: This compound is an irritant. It emits toxic fumes when heated to decomposition. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

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.

acetanilid

GRADES: TECHNICAL; CP.

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.

EXAMPLES ARE GIVEN OF SEPARATION OF COMBINATIONS OF ANALGESICS BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY.|METHOD OF DETERMINATION OF ACETANILIDE IN MIXED PHARMACEUTICAL PREPN.|AOAC Method Numbers 916.02 - 916.07. Acetanilid....in Drugs.|Microchemical Tests. AOAC Method Number 962.21. Barbituates in Drugs.

ACETANILIDE DETERMINED IN BLOOD BY GC; LOWER LIMIT OF DETECTION WAS 60 NG IN 100 MU L.|A GS-MS METHOD FOR ANALYSIS OF ACETANILIDE IN PLASMA OR URINE USING D-LABELED ANALOGS IS DESCRIBED.

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan|Cosmetics -> Stabilizing