6-(Methylsulfanyl)-2-nitroaniline

Base Information

• Chemical Name: 6-(Methylsulfanyl)-2-nitroaniline
• CAS No.: 494226-39-0
• Molecular Formula: C7H8N2O2S
• Molecular Weight: 184.219
• DSSTox Substance ID: DTXSID70448374
• Mol file: 494226-39-0.mol

Synonyms:6-(methylsulfanyl)-2-nitroaniline;494226-39-0;SCHEMBL6673312;DTXSID70448374;XKUGJYFYTQFEQQ-UHFFFAOYSA-N

Chemical Property of 6-(Methylsulfanyl)-2-nitroaniline

Chemical Property:

• PSA: 97.14000
• LogP: 3.00330
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 184.03064868
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=CC=CC(=C1N)[N+](=O)[O-]

Technology Process of 6-(Methylsulfanyl)-2-nitroaniline

There total 4 articles about 6-(Methylsulfanyl)-2-nitroaniline 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: 40.0%

1-(methylsulfanyl)-3-nitrobenzene (2524-76-7) → 6-(methylsulfanyl)-2-nitroaniline (494226-39-0)

Guidance literature:

With potassium tert-butylate; N-methoxylamine hydrochloride; copper(l) chloride; In DMF (N,N-dimethyl-formamide); at 5 - 20 ℃; for 3h;

Reference yield: 40.0%

1-(methylsulfanyl)-3-nitrobenzene (2524-76-7) → 1-amino-4-methylthio-2-nitrobenzene (23153-09-5) + 6-(methylsulfanyl)-2-nitroaniline (494226-39-0)

Guidance literature:

With potassium tert-butylate; N-methoxylamine hydrochloride; copper(l) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jm020367+

Reference yield:

3-nitrothiophenol (3814-18-4) → 6-(methylsulfanyl)-2-nitroaniline (494226-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 9.6 g / aq. KOH / 16 h / 20 °C

2: 40 percent / NH₂OMe*HCl; KOtBu; CuCl / dimethylformamide / 3 h / 20 °C

With potassium hydroxide; potassium tert-butylate; N-methoxylamine hydrochloride; copper(l) chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm020367+

upstream raw materials:

1-(methylsulfanyl)-3-nitrobenzene

3-nitrothiophenol

S-(3-nitrophenyl) dimethylthiocarbamate

Refernces

• 1、 Hay, Michael P.,Gamage, Swarna A.,Kovacs, Mary S.,Pruijn, Frederik B.,Anderson, Robert F.,Patterson, Adam V.,Wilson, William R.,Brown, J. Martin,Denny, William A.. "Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine". . p. 169 - 182. Retrieved 2007/10/03.