2-Amino-5-chloro-3-methylbenzonitrile

Base Information

• Chemical Name: 2-Amino-5-chloro-3-methylbenzonitrile
• CAS No.: 939990-03-1
• Molecular Formula: C₈H₇ClN₂
• Molecular Weight: 166.61
• DSSTox Substance ID: DTXSID801288037
• Mol file: 939990-03-1.mol

Synonyms:2-amino-5-chloro-3-methylbenzonitrile;939990-03-1;SCHEMBL12225147;DTXSID801288037;AKOS017529228;CS-0374650;EN300-323232;Z1262690933

Chemical Property of 2-Amino-5-chloro-3-methylbenzonitrile

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 166.0297759
• Heavy Atom Count: 11
• Complexity: 184

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1N)C#N)Cl

Technology Process of 2-Amino-5-chloro-3-methylbenzonitrile

There total 7 articles about 2-Amino-5-chloro-3-methylbenzonitrile 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: 84.0%

2-bromo-4-chloro-6-methylphenylamine (146948-68-7) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-amino-5-chloro-3-methylbenzonitrile (939990-03-1)

Guidance literature:

With 1-Butylimidazole; copper(l) iodide; sodium carbonate; In o-xylene; at 150 ℃; for 21h; Inert atmosphere; Pressure tube;

DOI:10.1002/adsc.201000200

Reference yield: 78.2%

2-methyl-4,6-dichloroaniline (30273-00-8) + copper(l) cyanide → 2-amino-5-chloro-3-methylbenzonitrile (939990-03-1)

Guidance literature:

With copper bromide; In N,N-dimethyl-formamide; at 90 - 95 ℃; for 18h; Temperature;

Reference yield: 27.0%

2-methyl-4,6-dichloroaniline (30273-00-8) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-amino-5-chloro-3-methylbenzonitrile (939990-03-1) + 4-amino-5-methylisophthalonitrile (98589-70-9)

Guidance literature:

With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-ethyl-N,N-diisopropylamine; XPhos; In butan-1-ol; at 80 ℃; for 5h; Temperature; Inert atmosphere;

upstream raw materials:

2-bromo-4-chloro-6-methylphenylamine

2-hydroxy-2-methylpropanenitrile

4-chloro-2-methylbenzeneamine

4-chloro-2-iodo-6-methyl-phenylamine

Downstream raw materials:

2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

2-amino-5-chloro-3-methylbenzoic acid