2-Chloro-6-nitro-benzenethiol

Base Information

• Chemical Name: 2-Chloro-6-nitro-benzenethiol
• CAS No.: 14371-77-8
• Molecular Formula: C6H4ClNO2S
• Molecular Weight: 189.622
• DSSTox Substance ID: DTXSID90457923
• Wikidata: Q82280993
• Mol file: 14371-77-8.mol

Synonyms:2-chloro-6-nitro-benzenethiol;2-chloro-6-nitrobenzenethiol;14371-77-8;6-chloro-2-nitrothiophenol;SCHEMBL2000175;DTXSID90457923;CKVPGKFNEHLOFL-UHFFFAOYSA-N

Chemical Property of 2-Chloro-6-nitro-benzenethiol

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 188.9651272
• Heavy Atom Count: 11
• Complexity: 161

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)S)[N+](=O)[O-]

Technology Process of 2-Chloro-6-nitro-benzenethiol

There total 1 articles about 2-Chloro-6-nitro-benzenethiol 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: 95.0%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 6-chloro-2-nitrothiophenol (14371-77-8)

Guidance literature:

1,2-Dichloro-3-nitrobenzene; With sodium sulfide; In dimethyl sulfoxide; at 20 ℃; for 18h;

With hydrogenchloride; In water; dimethyl sulfoxide; pH=4;

Reference yield: 76.7%

6-chloro-2-nitrothiophenol (14371-77-8) + methyl trans-3-(4-methoxyphenyl)glycidate (96125-49-4) → 3-(2-Chloro-6-nitro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (103921-05-7)

Guidance literature:

With zinc diacetate; In toluene; for 3h; Ambient temperature;

DOI:10.1021/jm00106a032

Reference yield: 68.0%

1-methylethyl 4-(2-bromo-3-ethoxy-3-oxopropyl)benzoate (1247021-53-9) + 6-chloro-2-nitrothiophenol (14371-77-8) → 1-methylethyl 4-{2-[(2-chloro-6-nitrophenyl)sulfanyl]-3-ethoxy-3-oxopropyl}benzoate (1247021-56-2)

Guidance literature:

6-chloro-2-nitrothiophenol; With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; for 0.5h; Inert atmosphere;

1-methylethyl 4-(2-bromo-3-ethoxy-3-oxopropyl)benzoate; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 6h; Inert atmosphere;

upstream raw materials:

1,2-Dichloro-3-nitrobenzene

Downstream raw materials:

3-(2-Chloro-6-nitro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester

methyl threo-3-<(2-amino-6-chlorophenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propionate

(+)-cis-(2S,3S)-9-chloro-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one

(-)-cis-(2R,3R)-9-chloro-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one

Refernces

• 1、 Battistoni, Paolo,Bruni, Paolo,Fava, Gabriele. "THE SYNTHESIS OF o-NITROBENZENETHIOLS: AN ADVANTAGEOUS NUCLEOPHILIC DISPLACEMENT ON o-CHLORONITROBENZENES". . p. 301 - 304. Retrieved 2007/10/02.