4-Amino-3-mercaptobenzonitrile

Base Information

• Chemical Name: 4-Amino-3-mercaptobenzonitrile
• CAS No.: 174658-22-1
• Molecular Formula: C7H6N2S
• Molecular Weight: 150.204
• European Community (EC) Number: 834-325-1
• DSSTox Substance ID: DTXSID80573904
• Wikidata: Q72438587
• Mol file: 174658-22-1.mol

Synonyms:4-Amino-3-mercaptobenzonitrile;174658-22-1;4-amino-3-sulfanylbenzonitrile;Benzonitrile, 4-amino-3-mercapto-;Benzonitrile, 4-amino-3-mercapto- (9CI);SCHEMBL1743125;DTXSID80573904;MXDAYVCCPKGPOE-UHFFFAOYSA-N;AT19654;SB76733;Benzonitrile,4-amino-3-mercapto-(9ci);EN300-126642

Chemical Property of 4-Amino-3-mercaptobenzonitrile

Chemical Property:

• PSA: 88.61000
• Density: 1.27
• LogP: 2.01038
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 150.02516937
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

4-Amino-3-mercaptobenzonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C#N)S)N

Technology Process of 4-Amino-3-mercaptobenzonitrile

There total 3 articles about 4-Amino-3-mercaptobenzonitrile 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: 93.7%

6-cyano benzothiazole (58249-61-9) → 4-amino-3-mercaptobenzonitrile (174658-22-1)

Guidance literature:

With ethylenediamine; In glycerol; at 90 ℃; for 0.25h; Inert atmosphere;

DOI:10.1016/j.bioorg.2019.103537

Reference yield:

2-amino-6-cyanobenzthiazole (19759-66-1) → 4-amino-3-mercaptobenzonitrile (174658-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / isoamyl nitrile / tetrahydrofuran / 0.5 h / Heating

2: NH₂NH₂*H₂O / ethanol / 1 h / 80 °C

With Isovaleronitrile; hydrazine hydrate; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.46.623

Reference yield:

4-Aminobenzonitrile (873-74-5) → 4-amino-3-mercaptobenzonitrile (174658-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / Br₂ / acetic acid / 3 h / 100 °C

2: 51 percent / isoamyl nitrile / tetrahydrofuran / 0.5 h / Heating

3: NH₂NH₂*H₂O / ethanol / 1 h / 80 °C

With Isovaleronitrile; bromine; hydrazine hydrate; In tetrahydrofuran; ethanol; acetic acid;

DOI:10.1248/cpb.46.623

upstream raw materials:

6-cyano benzothiazole

2-amino-6-cyanobenzthiazole

4-Aminobenzonitrile

Downstream raw materials:

2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-thiophenecarbonitrile

2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-furancarbonitrile

2-(4-carboxyphenyl)-5-(6-cyanobenzothiazol-2-yl)furan

2-(4-carboxyphenyl)-5-(6-cyanobenzothiazol-2-yl)thiophene

Refernces

• 1、 Racané, Livio,Kralj, Marijeta,?uman, Lidija,Stojkovi?, Ranko,Trali?-Kulenovi?, Vesna,Karminski-Zamola, Grace. "Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo". body text. p. 1038 - 1044. Retrieved 2010/04/26.