579-11-3

Basic information

• Product Name: N-CHLOROACETANILIDE
• Synonyms: N-CHLORO-N-PHENYL-;N-Chloroacetoanilide;N-Phenyl-N-chloroacetamide;N-chloro-N-phenyl-ethanamide;N-Chloroacetanilide;N-CHLOROACETANILIDE;n-chloro-acetanilid;N-Chloro-N-phenyl acetamide
• CAS NO: 579-11-3
• Molecular Formula: C₈H₈ClNO
• Molecular Weight: 169.60822
• Mol File: 579-11-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 92 °C
• Boiling Point: 234.2°C at 760 mmHg
• Flash Point: 95.5°C
• Appearance: /
• Density: 1.247g/cm³
• Vapor Pressure: 0.0535mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Freezer
• PKA: -0.90±0.50(Predicted)
• CAS DataBase Reference: N-CHLOROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CHLOROACETANILIDE(579-11-3)
• EPA Substance Registry System: N-CHLOROACETANILIDE(579-11-3)

Safety Data

• RIDADR: 3261
• RTECS: AE0350000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 579-11-3(Hazardous Substances Data)

Usage

General Description

N-Chloroacetanilide is a chemical compound that has the molecular formula C8H8ClNO2 and is commonly used as an intermediate in the production of various pharmaceuticals, dyes, and pesticides. It is a white to pale yellow crystalline solid with a slightly pungent odor. N-Chloroacetanilide is a chlorinated derivative of acetanilide and is a member of the acetanilide class of compounds, which are known for their analgesic and anti-inflammatory properties. It is a versatile compound that is also used in the synthesis of other organic compounds and as a reagent in chemical reactions. However, it should be handled with caution as it can cause skin and eye irritation and is harmful if swallowed or inhaled.

InChI:InChI=1/C8H8ClNO/c1-7(11)10(9)8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 507-40-4 tert-butylhypochlorite 
• 103-84-4 Acetanilid 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 539-03-7 N-(4-chlorophenyl)acetamide 
• 858208-38-5 2-(4-acetylamino-phenyl)-2-methyl-propionic acid methyl ester 
• 103-84-4 Acetanilid 
• 103-88-8 4-bromoacetanilide 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 6975-29-7 N-(2,4-dichlorophenyl)acetamide 
• 2116-41-8 1-Acetyl-1-phenylhydrazin 
• 121-87-9 2-Chloro-4-nitroaniline 
• 6049-42-9 N,N'-diacetyl-N,N'-diphenylhydrazine 
• 22421-97-2 methyl 2-chloroisobutyrate 
• 17072-58-1 tetramethyl-succinic acid dimethyl ester 
• 125989-73-3 N-Phenyl-2-[4-(4-phenyl-2,3-dihydro-benzo[b][1,4]thiazepin-2-yl)-phenoxy]-acetamide 
• 874-69-1 N-phenylacetimidoyl chloride 
• 58061-19-1 hypochlorous acid phenyl ester 

Relevant articles and documents

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Method for synthesizing 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate

The invention relates to a method for synthesizing an efavirenz intermediate, in particular to a method for synthesizing a 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate. The method includes the following steps that an acylating agent is added to aniline in an organic solvent, aniline is subjected to an acylation reaction under the alkaline condition and at the temperature of 5-15 DEG C to obtain a compound A, the compound A reacts with a chlorinating agent under the alkalescent condition to obtain a compound B, the compound B reacts with trifluoroacetic acid ethyl ester under the action of butyl lithium to obtain a compound C, the compound C and hydrochloric acid are subjected to a reflux reaction at 60-65 DEG C, and the 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate is obtained. Reaction conditions are mild, energy consumption is greatly reduced, raw materials in use are easy to obtain, cost is low, and pollution is little. The method is easy to operate, the total yield can reach 77.2%, the purity can reach 99% or above, product quality is good, and the method is suitable for industrial production.

Nucleophilic Substitution at Centers Other than Carbon: Reaction at the Chlorine of N-Chloroacetanilides with Triethylamine as the Nucleophile

The reaction between triethylamine (TEA) and a series of para-substituted N-chloroacetanilides has been studied in aqueous solution buffered to pHs between 1 and 5.In these reactions, the exclusive product derived from the aromatic moiety is the corresponding acetanilide.The reaction occurs via two parallel pseudo-second-order paths, one acid catalyzed (the Orton-like mechanism), the other uncatalyzed.The uncatalyzed reaction is accelerated by the presence of electron-withdrawing substituents on the aromatic ring and can best be represented as nucleophilic displacement at chlorine.It therefore appears to be the prototype of a convenient class of reactions for the study of displacement reactions at chlorine.The ρ value for this reaction is 3.87 indicating substantial negative charge buildup in the aromatic ring during the transition state.The acid-catalyzed reaction is more complex, presumably involving a protonation equilibrium for the N-chloroacetanilide prior to the rate-determining step similar to that in the Orton reaction.