N-(5-Chloro-2-methylphenyl)acetamide

Base Information

• Chemical Name: N-(5-Chloro-2-methylphenyl)acetamide
• CAS No.: 5900-55-0
• Molecular Formula: C9H10ClNO
• Molecular Weight: 183.637
• European Community (EC) Number: 227-592-5
• NSC Number: 404301
• UNII: CE65MZX3VH
• DSSTox Substance ID: DTXSID30207742
• Nikkaji Number: J223.871C
• Wikidata: Q72454510
• Mol file: 5900-55-0.mol

Synonyms:N-(5-Chloro-2-methylphenyl)acetamide;5900-55-0;2-Acetamino-4-chlorotoluene;o-Acetotoluidide, 5'-chloro-;CE65MZX3VH;5-Chloro-2-methylacetanilide;Acetamide, N-(5-chloro-2-methylphenyl)-;5'-Chloro-2'-methylacetanilide;EINECS 227-592-5;NSC-404301;5-Chloro-o-acetotoluidide;NSC404301;UNII-CE65MZX3VH;N-(5-CHLORO-2-METHYL-PHENYL)-ACETAMIDE;SCHEMBL6106176;DTXSID30207742;2-ACETAMIDO-4-CHLOROTOLUENE;MFCD00018743;AKOS001044998;Aniline, N-acetyl-3-chloro-6-methyl-;NSC 404301;N-(5-Chloro-2-methylphenyl)acetamide #;AC-11163;TS-02560;Acetamide, N-(5-chloro-2-methyl)phenyl-;CS-0190589;FT-0746725;E89338;AC-907/25004932;W-105349;Z27065719

Chemical Property of N-(5-Chloro-2-methylphenyl)acetamide

Chemical Property:

• Melting Point: 129-130 °C
• Refractive Index: 1.592
• Boiling Point: 319.6 °C at 760 mmHg
• PKA: 14.46±0.70(Predicted)
• Flash Point: 147.1 °C
• Density: 1.218 g/cm³
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• 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:

99% ^*data from raw suppliers

5-Chloro-o-acetotoluidide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)Cl)NC(=O)C
• Uses: 5-Chloro-o-acetotoluidide, is an intermediate for the synthesis of Metolazone (M338750), which is a diruetic and an antihypertensive.

Technology Process of N-(5-Chloro-2-methylphenyl)acetamide

There total 10 articles about N-(5-Chloro-2-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: 94.0%

4-chloro-2-nitrotoluene (89-59-8) + acetic anhydride (108-24-7) → N-(5-chloro-2-methylphenyl)acetamide (5900-55-0)

Guidance literature:

4-chloro-2-nitrotoluene; With sodium tetrahydroborate; In water; at 60 - 70 ℃; Green chemistry;

acetic anhydride; In water; at 60 - 70 ℃; Green chemistry;

DOI:10.1007/s13738-018-1469-x

Reference yield: 94.0%

acetic anhydride (108-24-7) + 5-chloro-2-methyl-benzenamine (95-79-4) → N-(5-chloro-2-methylphenyl)acetamide (5900-55-0)

Guidance literature:

With Ni₂B-Cu₂O nanocomposite; In neat (no solvent); at 40 ℃; for 0.0333333h; Reagent/catalyst;

DOI:10.1007/s11164-018-3559-x

Reference yield: 61.7%

acetyl chloride (75-36-5) + 5-chloro-2-methyl-benzenamine (95-79-4) → N-(5-chloro-2-methylphenyl)acetamide (5900-55-0)

Guidance literature:

With TEA; In dichloromethane; at 0 - 25 ℃;

upstream raw materials:

acetic anhydride

5-chloro-2-methyl-benzenamine

acetic acid

para-chlorotoluene

Downstream raw materials:

2-amino-4-chloro-benzoic acid methyl ester

2,4,7-trichloroquinoline

2-(2-ethoxycarbonyl-acetylamino)-4-chloro-benzoic acid methyl ester

3-chloro-6-methyl-2-nitro-aniline

Refernces

• 1、 Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein. "Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water". . p. 3289 - 3312. Retrieved 2021/05/11.
• 2、 Zeynizadeh, Behzad,Younesi, Reza,Mousavi, Hossein. "Ni2B@Cu2O and Ni2B@CuCl2: two new simple and efficient nanocatalysts for?the green one-pot reductive acetylation of nitroarenes and direct N-acetylation of arylamines using solvent-free mechanochemical grinding". . p. 7331 - 7352. Retrieved 2018/08/25.