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Your Location：Home>Product Center >> Pharmaceutical intermediates >> N-Acetylaniline
  • N-Acetylaniline
Name:N-Acetylaniline
CAS No:103-84-4

PRODUCT DESCRIPTION

【Name】
N-Acetylaniline
【Iupac name】
N-phenylacetamide
【CAS Registry number】
103-84-4
【Synonyms】
Acetanilide
Antifebrin
Acetanilide,(N-Phenylacetamide)
N-Phenylacetamide
【EINECS(EC#)】
203-150-7
【Molecular Formula】
C8H9NO (Products with the same molecular formula)
【Molecular Weight】
135.16
【Inchi】
InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
【InChIKey】
FZERHIULMFGESH-UHFFFAOYSA-N
【Canonical SMILES】
CC(=O)NC1=CC=CC=C1
【MOL File】
103-84-4.mol

Chemical and Physical Properties

【Appearance】
white leaflets or flakes
【Density】
1.22
【Melting Point】
111-115℃
【Boiling Point】
304℃
【Vapour】
0.00111mmHg at 25°C
【Refractive Index】
1.552
【Flash Point】
173℃
【Water】
5 g/L (25℃)
【Solubilities】
Soluble in hot water
【Color/Form】
ORTHORHOMBIC PLATES OR SCALES FROM WATER
WHITE SHINING CRYSTALLINE SCALES
White, shining crystalline leaflets or white crystalline powder.
Colorless, glossy, crystalline material.
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
【HS Code】
29242995
【Storage temp】
Keep away from heat and flame. Store in a tightly closed container. Keep from contact with oxidizing materials. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep away from strong bases.
【Spectral properties】
INDEX OF REFRACTION: 1.515 (ALPHA), 1.620 (BETA), GREATER THAN 1.733 (GAMMA); PKA: 1
MAX ABSORPTION (ALCOHOL): 242 NM (LOG E= 4.16); SADTLER REFERENCE NUMBER: 160 (IR, PRISM); 49 (IR, GRATING); 63 (UV); 5235 (NMR)
IR: 2230 (Sadtler Research Laboratories Prism Collection)
UV: 599 (Sadtler Research Laboratories Spectral Collection)
MASS: 304 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Intense mass spectral peaks: 93 m/z, 135 m/z
【Computed Properties】
Molecular Weight:135.16316 [g/mol]
Molecular Formula:C8H9NO
XLogP3:1.2
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:1
Tautomer Count:3
Exact Mass:135.068414
MonoIsotopic Mass:135.068414
Topological Polar Surface Area:29.1
Heavy Atom Count:10
Formal Charge:0
Complexity:116
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/37/38
【Safety Statements 】
S22;S26;S36
【Safety】
Hazard Codes:Xn
Risk Statements:22-36/37/38
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-26-36
22:Do not breathe dust
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany:1
HS Code:29242995
Hazardous Substances Data:103-84-4(Hazardous Substances Data)
【Transport】
25kgs
【Formulations/Preparations】
GRADES: TECHNICAL; CP.
【Reactivities and Incompatibilities】
SEE ANILINE...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.
【Specification】

grey or white powder or flakes
Safety Statements:22-26-36
22:Do not breathe dust
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
【Octanol/Water Partition Coefficient】
Log Kow= 1.16
【Disposal Methods】
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 deg 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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

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.
U.S. Exports

(1986) ND
U.S. Imports

(1986) ND
U.S. Production

(1986) ND
【Usage】

Manufacture of medicinals, dyes, stabilizer for hydrogen peroxide, as addn to cellulose ester varnishes.

Biomedical Effects and Toxicity

【Therapeutic Uses】
IT IS PARTICULARLY EFFECTIVE AS AN ANALGESIC IN PAIN OF THE NEURALGIC TYPE...
MEDICATION (VET): ANALGESIC, ANTIPYRETIC AGENT
【Biomedical Effects and Toxicity】
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.
REPLACEMENT OF SODIUM ION BY POTASSIUM ION /IN PERFUSATE/ RESULTED IN...15-30% REDUCTION FOR ACETANILIDE TRANSPORT /THROUGH RAT INTESTINE/.
WHEN INTESTINAL EPITHELIAL CELLS WERE REMOVED BY TREATMENT WITH EDETIC ACID, NO DIRECTIONAL PERMEABILITY WAS FOUND FOR...ACETANILIDE IN SODIUM PHOSPHATE BUFFER.../TRANSFER RATES OF ACETANILIDE THROUGH INTESTINAL MUSCLE LAYER WERE APPROX 4 TIMES THOSE FOUND FOR UNTREATED SEGMENTS./
ONE G DOSE ADMIN ORALLY REACHED CONCN OF 0.9% IN BLOOD IN 1-2 HR. 2 G DOSE ADMIN ORALLY REACHED CONCN OF 1.7% IN BLOOD IN 1-2 HR. AFTER 5 HR, 50% HAD BEEN EXCRETED IN URINE; AFTER 10 HR, 80%; AFTER 24 HR, 98%. /FROM TABLE/
PLASMA ELIMINATION RATES OF PHENACETIN, ACETANILIDE & THEOPHYLLINE DETERMINED IN 32 HEALTHY SUBJECTS IN EFFORT TO FIND DRUGS RESEMBLING BENZO(A)PYRENE IN METABOLISM.
ACETANILIDE HYDROXYLATION IN MAN WAS SATURATED BY AS SMALL AS 0.5 G DOSE.
IN HEALTHY SUBJECTS GIVEN ACETANILIDE ORALLY AT 50 MG/KG, PLASMA CLEARANCE VALUES VARIED FROM 12.4 TO 25.1 L/HR.
METAB OF (3)H-ACETANILIDE STUDIED IN RATS AFTER SINGLE IP DOSE (200 MG/KG), 1-5 DAYS OF CONTINUOUS FEEDING OF 0.8% IN DIET, & @ WEEKLY INTERVALS DURING 4 WK OF SUCH FEEDING. 3 GROUPS EXCRETED 56, 62 & 86% OF DOSE, RESPECTIVELY, IN 24 HR SAMPLES OF URINE.
1 WK CONTINUOUS FEEDING 0.8% (3)H-ACETANILID TO RATS. BLOOD LEVEL RADIOACTIVITY 11 FOLD HIGHER THAN AFTER SINGLE DOSE (200 MG/KG IP). LIVER CONTAINED 15 TIMES MORE ISOTOPE @ 4 WK (0.8% OF DIET) & BINDING TO RNA, DNA & LIVER PROTEINS 180, 15 & 33 FOLD HIGHER THAN AFTER 1 DOSE.
... Female /Wistar/ rats were orally admin (14(C) labeled acetanilide and nitrobenzene. ... Tissue concn of nitrobenzene were significantly higher than acetanilide. within 24 hr, 78% of the acetanilide dose, but only 50% of the nitrobenzene dose appeared in the urine. Only 33% of the acetanilide dose was excreted in the feces, versus 15.5% of nitrobenzene. More nitrobenzene than acetanilide metabolites were bound to hemoglobin and plasma proteins. Binding occurred through the reaction of nitrobenzene with sulfhydryl groups of cysteine as a sulfinic acid amide. ... ?Results indicate/ that both aniline and nitrobenzene yield hemoglobin binding metabolites in rats. [Albrecht W, Neumann HG; Arch Toxicol 57 (1): 1-5 (1985)] PubMed Abstract
The effects of a single oral dose of ethanol 25 g and 50 g on the disposition of oral acetanilide were studied in 10 healthy adults and 10 patients with chronic nonalcholic liver disease. In healthy adults, ethanol produced a dose dependent incr in acetanilide half life and a decr in acetanilide clearance. In patients with liver disease, ethanol produced a similar proportional change in acetanilide half life and clearance, but these were less consistent. ... Liver disease itself was associated with an reduction in clearance. It was concluded that single oral doses of ethanol, comparable to those consumed during social drinking, may inhibit some forms of microsomal oxidation and may have important clinical implications. [McKay J et al; Br J Clin Pharmacol 14: 501-4 (1982)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
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 deg 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).

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