4-Chloro-N1-methylbenzene-1,2-diamine

Base Information

• Chemical Name: 4-Chloro-N1-methylbenzene-1,2-diamine
• CAS No.: 59681-66-2
• Molecular Formula: C7H9ClN2
• Molecular Weight: 156.615
• Mol file: 59681-66-2.mol

Synonyms:4-Chloro-N1-methylbenzene-1,2-diamine;4-chloro-N1-methyl-1,2-Benzenediamine

Chemical Property of 4-Chloro-N1-methylbenzene-1,2-diamine

Chemical Property:

• Boiling Point: 309.5±27.0 °C(Predicted)
• PKA: 5.49±0.11(Predicted)
• PSA: 38.05000
• Density: 1.272±0.06 g/cm3(Predicted)
• LogP: 2.61810
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98.5% ^*data from raw suppliers

4-Chloro-N1-methylbenzene-1,2-diamine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Chloro-N1-methylbenzene-1,2-diamine

There total 5 articles about 4-Chloro-N1-methylbenzene-1,2-diamine 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: 42.0%

methylamine (74-89-5) + 2,5-dichloronitrobenzene (89-61-2) → 4-chloro-1-N-methylbenzene-1,2-diamine (59681-66-2)

Guidance literature:

methylamine; 2,5-dichloronitrobenzene; In ethanol; at 20 - 80 ℃; for 15h;

With hydrogenchloride; zinc; In ethanol; water; at 20 ℃; for 3h;

With sodium hydroxide; In ethanol; water;

Reference yield: 40.0%

4-chloro-N-methyl-2-nitroaniline (15950-17-1) → 4-chloro-1-N-methylbenzene-1,2-diamine (59681-66-2)

Guidance literature:

With iron; acetic acid; at 60 ℃; for 1h;

DOI:10.1002/anie.201504455

Reference yield:

4-Chloro-2-nitroaniline (89-63-4) → 4-chloro-1-N-methylbenzene-1,2-diamine (59681-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 60percent NaH in oil / dimethylformamide

2: 1.5 g / hydrogen / 10percent Pd/C / methanol / 2280 Torr

With hydrogen; sodium hydride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.3987/com-98-8108

upstream raw materials:

4-chloro-N-methyl-2-nitroaniline

2-fluoro-5-chloronitrobenzene

4-Chloro-2-nitroaniline

methylamine

Downstream raw materials:

(N-methyl-5-chloro-1H-benzimidazole-2-yl)methanol

5-chloro-1-methyl-1H-benzimidazol-2-amine

5-chloro-1,3-dihydro-1-methyl-2H-benzimidazol-2-one

5-chloro-1-methyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

Refernces

• 1、 Mukhina, Olga A.,Kuznetsov, Dmitry M.,Cowger, Teresa M.,Kutateladze, Andrei G.. "Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles". supporting information. p. 11516 - 11520. Retrieved 2015/11/03.
• 2、 Windisch, Marc Peter,Jo, Suyeon,Kim, Hee-Young,Kim, Soo-Hyun,Kim, Keumhyun,Kong, Sunju,Jeong, Hyangsuk,Ahn, Sujin,No, Zaesung,Hwang, Jong Yeon. "Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action". . p. 35 - 42. Retrieved 2014/04/17.