N-(4-Chlorophenyl)acetamide

Log Kow = 2.12

1.87

PRACTICALLY INSOL IN /COLD/ WATER; READILY SOL IN ALC, ETHER; READILY SOL IN CARBON DISULFIDE; SLIGHTLY SOL IN CARBON TETRACHLORIDE, BENZENE

SOL IN HOT WATER

Warning

H315 (98%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Causes Heinz body formation, hemolysis, and spleen enlargement in rats; Exhibits nephrotoxic and hepatotoxic potential in intraperitoneal studies of rats; [HSDB] Causes decreased body temperature in intraperitoneal lethal-dose studies of rats; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS] See Acetanilide.

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.

TERRESTRIAL FATE: An estimated Koc of 340(1,SRC) based on an experimental log Kow(2) suggests that p-chloroacetanilide will have moderate mobility in soil(3,SRC); leaching of this compound may be possible(SRC). Incomplete information is available regarding the biodegradation potential of p-chloroacetanilide; however, p-chloroacetanilide was partially biodegraded (from 30-75% of the theoretical methane production) under anaerobic conditions using a secondary digester sludge inoculum over 8 weeks(4). p-Chloroacetanilide will not volatilize from moist soil surfaces based on an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole(5,SRC).

AQUATIC FATE: Incomplete information is available regarding the biodegradation potential of p-chloroacetanilide; however, p-chloroacetanilide was partially biodegraded (from 30-75% of the theoretical methane production) under anaerobic conditions over an 8 week period using a secondary digester sludge inoculum(1). An estimated BCF value of 24(3,SRC), based on an experimental log Kow(2), indicates that p-chloroacetanilide will not bioconcentrate in aquatic organisms(SRC). p-Chloroacetanilide is not expected to volatilize from water surfaces based on a Henry's Law constant of 4.6X10-9 atm-cu m/mole(4,SRC).

ATMOSPHERIC FATE: Based on an estimated vapor pressure of 8.33X10-6 mm Hg at 25 °C(1,SRC), p-chloroacetanilide will exist in both the vapor phase and particulate phase in the ambient atmosphere(2,SRC). p-Chloroacetanilide will degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 4 days(3,SRC). Particulate-phase p-chloroacetanilide may be removed physically from air by wet and dry deposition(SRC).

Based on an experimental log Kow of 2.12(1), the Koc of p-chloroacetanilide is estimated as approximately 340 using a regression-derived equation(2,SRC). According to a suggested classification scheme, this estimated Koc value suggests that p-chloroacetanilide has moderate mobility in soil(3,SRC).

A BCF of 24 was calculated for p-chloroacetanilide, using an experimental log Kow of 2.12(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that p-chloroacetanilide will not bioconcentrate in aquatic organisms(2,SRC).

P-CHLOROACETANILIDE, CONTAMINANT OF PHENACETIN, CAUSED HEINZ BODY FORMATION, HEMOLYSIS, & SPLEEN ENLARGEMENT IN RATS (PHENACETIN HAS BEEN IMPLICATED IN THESE). PARA-PHENETIDINE, A PHENACETIN MINOR METABOLITE, PROBABLY SHARES RESPONSIBILITY FOR THE HEMOLYTIC PROCESS.

A major metabolic pathway for the chloroanilines is via acetylation of the amino group to form chloroacetanilides. ... This study was to examine the hepato- and nephrotoxic potential of the three monochloroacetanilides to determine if N-acetylation is an important biotransformation step for activation or detoxification of the chloroanilines in organ-directed toxicity. In one set of experiments male Fischer 344 rats (4 rats/group) were injected intraperitoneally (ip) with a Chloroacetanilide (CAA) (0.5, 1.0 or 1.5 mmol/kg) or vehicle and renal function monitored for 24 or 48 hr. Liver function and tissue morphology also were determined at 24 or 48 hr. None of the chloroacetanilide were marked nephrotoxicants at doses of 0.5 or 1.0 mmol/kg. However 4-chloroacetanilides (1:5 mmol/kg) induced an increase in blood urea nitrogen concentration and kidney weight at 24 hr and 3-chloroacenilide (1.5 mmol/kg) was lethal within 24 hr. The decreasing order of in vivo nephrotoxic potential was found to be 4-chloroacetanilide 3-chloroacetanilide > 2-chloroacetanilide. Based on the elevation of ALT/GPT activity at 48 hr the order of hepatotoxic potential was found to be 4-chloroacaetanilide > 3-chloroacatanilide, 2-chloroacetanilide. In a second set of experiments, the in vitro effect of the chloroacetanilides on organic ion transport by renal cortical slices was examined. Both 3- and 4-chloroacetanilide decreased organic ion accumulation at bath concentrations of 10-5 M or greater, while 2-chloroacatanilide had no effect at concentrations up to 10-3 M. ... The order of nephrotoxic and hepatotoxic potential among the chloroacetanilide isomers is different than among the chloroanilines and the chloroacetanilides were generally less potent as hepatotoxicants or nephrotoxicants than the corresponding chloroaniline.

The rate constant for the vapor-phase reaction of p-chloroacetanilide with photochemically produced hydroxyl radicals has been estimated as 3.9X10-12 cu cm/molecule-sec at 25 °C(1,SRC). This value corresponds to an atmospheric half-life for p-chloroacetanilide of about 4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals/cu cm (1,SRC).

p-Chloroacetanilide may be found in the environment as a metabolite of 4-chloroaniline. If released to the atmosphere, p-chloroacetanilide will exist in both the vapor phase and the particulate phase. In the vapor phase, p-chloroacetanilide will react with hydroxyl radicals with an estimated half-life of 4 days. Particulate phase p-chloroacetanilide may be removed from the atmosphere by wet and dry deposition. Based on an estimated Koc of 340, p-chloroacetanilide should be moderately mobile in soil; some leaching may be possible. Insufficient information is available for the determination of p-chloroacetanilide's biodegradability; however, p-chloroacetanilide was partially biodegraded (from 30-75% of the theoretical methane production) under anaerobic conditions using a secondary digester sludge inoculum over 8 weeks. p-Chloroacetanilide is not expected to volatilize from water surfaces or to bioconcentrate in aquatic organisms. (SRC)

YIELDS 2-ACETAMIDO-5-CHLOROPHENOL; 4-ACETAMIDO-2-CHLOROPHENOL; 5-ACETAMIDO-2-CHLOROPHENOL; & P-ACETAMIDOPHENOL IN RATS. /FROM TABLE/

P-CHLOROACETANILIDE GIVES P-CHLOROANILINE IN CHICK & RAT. /FROM TABLE/

OXIDATION OF 4-CHLOROACETANILIDE TO N-HYDROXY-4-CHLOROACETANILIDE IS CATALYZED BY HAMSTER-LIVER MICROSOMES. THE ENZYME, A TYPICAL MONO-OXYGENASE, IS INDUCED BY 3-METHYLCHOLANTHRENE, BUT NOT BY PHENOBARBITAL. PRESENCE OF 0.1 MOLAR SODIUM FLUORIDE ENHANCES RATE OF REACTION.

4-CHLOROACETANILIDE WAS OXIDIZED TO 4-CHLOROGLYCOLANILIDE & 4-CHLOROOXANILIC ACID IN RABBIT (18% & 20% OF THE DOSE, RESPECTIVELY, IN 24 HR URINE), BUT ONLY TO 4-CHLOROGLYCOLANILIDE (11%) IN PIG.

For more Metabolism/Metabolites (Complete) data for P-CHLOROACETANILIDE (17 total), please visit the HSDB record page.

A soil bacteria metabolite of 4-chloroaniline and contaminant of phenacetin; Used as research chemical; Not commercially produced in the US; [HSDB]

RESEARCH CHEMICAL

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

REACTION OF P-CHLOROANILINE AND ACETIC ANHYDRIDE

Preparation of m-, o-, and p-isomers.