N-(2-chloro-6-methylphenyl)acetamide

Base Information

• Chemical Name: N-(2-chloro-6-methylphenyl)acetamide
• CAS No.: 21352-09-0
• Molecular Formula: C9H10 Cl N O
• Molecular Weight: 183.637
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60401019
• Nikkaji Number: J491.062A
• Wikidata: Q82204085
• Mol file: 21352-09-0.mol

Synonyms:N-(2-chloro-6-methylphenyl)acetamide;21352-09-0;2-CHLORO-6-METHYLACETANILINE;2-Chloro-6-methylacetanilin;2'-Chloro-6'-methylacetanilide;o-Acetotoluidide, 6'-chloro-;3-chloro-2-acetylaminotoluene;SCHEMBL2921682;DTXSID60401019;VFGNPYWQUOSOSR-UHFFFAOYSA-N;AKOS003107812;N-(6-chloro-2-methyl-phenyl)-acetamide;CS-0017716

Chemical Property of N-(2-chloro-6-methylphenyl)acetamide

Chemical Property:

• PSA: 29.10000
• LogP: 2.67980
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 183.0450916
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

96% ^*data from raw suppliers

2-Chloro-6-methylacetanilin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)Cl)NC(=O)C
• Uses: 2-Chloro-6-methylacetanilin (cas# 21352-09-0) is a useful reagent for electrophilic substitution of 2'',4''- and 2'',6''-dihaloacetanilides.

Technology Process of N-(2-chloro-6-methylphenyl)acetamide

There total 13 articles about N-(2-chloro-6-methylphenyl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.7%

N-(2-methylphenyl)acetamide (120-66-1) → 4-chloro-2-methylacetanilide (5202-86-8) + N-(6-chloro-2-methylphenyl)acetamide (21352-09-0)

Guidance literature:

With 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate; N-chloro-succinimide; camphor-10-sulfonic acid; In 1,4-dioxane; at 25 ℃; for 24h;

DOI:10.1055/s-0035-1560376

Reference yield: 74.0%

N-ethanoyl-2-methylphenylhydroxyamine (70786-65-1) → N-(6-chloro-2-methylphenyl)acetamide (21352-09-0)

Guidance literature:

With thionyl chloride; In diethyl ether; for 1h; T < 5 deg C;

Reference yield: 66.0%

N-(2-methylphenyl)acetamide (120-66-1) → N-(6-chloro-2-methylphenyl)acetamide (21352-09-0)

Guidance literature:

With N-chloro-succinimide; cobalt acetylacetonate; trifluoroacetic acid; silver(l) oxide; In 1,2-dichloro-ethane; at 60 ℃; for 16h; regioselective reaction;

DOI:10.1039/c8ob01448e

upstream raw materials:

acetic anhydride

2-chloro-6-methylaniline

N-ethanoyl-2-methylphenylhydroxyamine

1-methyl-2-nitrobenzene

Downstream raw materials:

2-chloro-6-methylaniline

(S)-(-)-6,6'-dichloro-2,2'-diphenic acid

(R)-(+)-6,6'-dichloro-2,2'-diphenic acid

6,6'-dichloro-2,2'-diphenic acid

Refernces

• 1、 Li, Ze-lin,Sun, Kang-kang,Cai, Chun. "Cobalt(II)-catalyzed regioselective C-H halogenation of anilides". supporting information. p. 5433 - 5440. Retrieved 2018/08/12.
• 2、 Bedford, Robin B.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.. "Mild C - H halogenation of anilides and the isolation of an unusual palladium(I)-palladium(II) species". supporting information; experimental part. p. 5524 - 5527. Retrieved 2011/07/31.