2-Chloro-5-(methylsulfanyl)aniline

Base Information

• Chemical Name: 2-Chloro-5-(methylsulfanyl)aniline
• CAS No.: 15945-75-2
• Molecular Formula: C7H8 Cl N S
• Molecular Weight: 173.666
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID10445645
• Wikidata: Q82264145
• Mol file: 15945-75-2.mol

Synonyms:15945-75-2;2-CHLORO-5-(METHYLSULFANYL)ANILINE;2-chloro-5-methylsulfanylaniline;2-CHLORO-5-METHYLSULFANYL-PHENYLAMINE;2-chloro-5-methylsulfanylphenylamine;SCHEMBL3793427;2-Chloro-5-(methylthio)aniline;DTXSID10445645;AKOS006326424;FT-0702447;EN300-139298;F2167-8493

Chemical Property of 2-Chloro-5-(methylsulfanyl)aniline

Chemical Property:

• PSA: 51.32000
• LogP: 3.22530
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.0065981
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99%min ^*data from raw suppliers

2-CHLORO-5-METHYLSULFANYL PHENYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=CC(=C(C=C1)Cl)N

Technology Process of 2-Chloro-5-(methylsulfanyl)aniline

There total 3 articles about 2-Chloro-5-(methylsulfanyl)aniline 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: 79.0%

2-chloro-5-(methylthio)benzoic acid (51546-12-4) → 2-chloro-5-(methylthio)aniline (15945-75-2)

Guidance literature:

2-chloro-5-(methylthio)benzoic acid; With diphenyl phosphoryl azide; triethylamine; In tert-butyl alcohol; for 6h; Heating;

With hydrogenchloride; In tetrahydrofuran; for 6h; Heating;

DOI:10.1016/S0960-894X(00)00695-8

Reference yield:

1-chloro-4-(methylthio)-2-nitrobenzene (1199-36-6) → 2-chloro-5-(methylthio)aniline (15945-75-2) + Sodium; 2-amino-4-methylsulfanyl-benzenethiolate

Guidance literature:

With sodium sulfide; In water; Heating;

DOI:10.1080/00397919708004210

Reference yield:

1-chloro-4-(methylthio)-2-nitrobenzene (1199-36-6) + acetic anhydride (108-24-7) → 2-chloro-5-(methylthio)aniline (15945-75-2) + 2-methyl-5-(methylthio)benzothiazole

Guidance literature:

With sodium sulfide; Yield given. Multistep reaction; 1.) water, reflux, overnight, 2.) acetic acid, water, reflux, overnight;

DOI:10.1080/00397919708004210

upstream raw materials:

1-chloro-4-(methylthio)-2-nitrobenzene

acetic anhydride

2-chloro-5-(methylthio)benzoic acid

Downstream raw materials:

2-chloro-5-methanesulfinyl-phenyl-cyanamide

Refernces

• 1、 Padmanabhan, Seetharamaiyer,Perlman, Michael E,Zhang, Lu,Moore, Deke,Zhou, Dan,Fischer, James B,Durant, Graham J,McBurney, Robert N. "Identification and characterization of a potential ischemia-selective N-methyl-D-aspartate (NMDA) receptor ion-channel blocker, CNS 5788". . p. 501 - 504. Retrieved 2007/10/03.
• 2、 Hu, Lain-Yen,Quo, Junqing,Magar, Sharad S.,Fischer, James B.,Burke-Howie, Kathleen J.,Durant, Graham J.. "Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N'-(3-substituted phenyl)-N'-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers". . p. 4281 - 4289. Retrieved 2007/10/03.