N-(4-Chlorophenyl)acetamide
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N-(4-Chlorophenyl)acetamide
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CAS No:
539-03-7
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Formula:
C8H8ClNO
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Chemical Name:
N-(4-Chlorophenyl)acetamide
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Synonyms:
Acetamide,N-(4-chlorophenyl)-;Acetanilide,4′-chloro-;N-(4-Chlorophenyl)acetamide;p-Chloroacetanilide;4′-Chloroacetanilide;N-Acetyl-p-chloroaniline;N-(p-Chlorophenyl)acetamide;N-Acetyl-4-chloroaniline;NSC 40563;NSC 444;N-(4-Chlorophenyl)ethaneamide
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CAS No:
Description
white or greyish-beige crystalline powder
4-chloroacetanilide is acetamide substituted on nitrogen by a para-chlorophenyl group. It is a member of acetamides and a member of monochlorobenzenes.
N-(4-Chlorophenyl)acetamide Basic Attributes
169.61
169.61
509638
208-707-8
6I0LI34G5J
40563|444
DTXSID0060228
ORTHORHOMBIC CRYSTALS FROM AQ GLACIAL ACETIC ACID, ALCOHOL, OR ACETONE
2924299090
Characteristics
29.1
2.12
White or grayish-beige Crystalline Powder
1.385 g/cm3 @ Temp: 22 °C
178-179 °C
333 °C
333°C
1.591
Insoluble in water.dioxane: 50 mg/mL hot, clear
Store below +30°C.
Peritoneal-rat LD50: 350 mg/kg; peritoneal-mouse LD50: 730 mg/kg
Thermal decomposition releases toxic nitrogen oxides and chloride fumes
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
AE1001000
Xi
The warehouse is low-temperature, ventilated and dry
P261-P305 + P351 + P338
H315-H319-H335
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.
|Warning|H315 (97.83%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
moderately toxic
LD50 Mouse ip was 755 mg/kg
p-Chloroacetanilide was formed as a metabolite by soil bacteria exposed to 4-chloroaniline(1).
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).
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).
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).
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).
The Henry's Law constant for p-chloroacetanilide is estimated as 4.6X10-6 atm-cu m/mole(1,SRC). This value indicates that p-chloroacetanilide will essentially not volatilize from water surfaces(2,SRC).
Drug Information
IN MICE, BUCCAL ABSORPTION WAS RELATED PARABOLICALLY TO ANALGESIC ACTIVITY: CMPD INCL P-CHLOROACETANILIDE.
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.
4-chloroacetanilide
N-(4-Chlorophenyl)acetamide Use and Manufacturing
REACTION OF P-CHLOROANILINE AND ACETIC ANHYDRIDE|Preparation of m-, o-, and p-isomers.
Used as organic synthesis and dye intermediate
(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US
Acetamide, N-(4-chlorophenyl)-: ACTIVE
CORRELATION OF CHROMATOGRAPHICALLY OBTAINED SUBSTITUENT CONSTANTS & ANALGESIC ACTIVITY. THE P-SUBSTITUTED ACETANILIDES WERE INCLUDED.|GLC DETERMINATION OF P-CHLORACETANILIDE IN ACETAMINOPHEN. AS LITTLE AS 25 PPM OF P-CHLOROACETANILIDE WAS DETERMNINED.
Computed Properties
Molecular Weight:169.61
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:169.0294416
Monoisotopic Mass:169.0294416
Topological Polar Surface Area:29.1
Heavy Atom Count:11
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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