4-Bromothiophenol

Base Information

• Chemical Name: 4-Bromothiophenol
• CAS No.: 106-53-6
• Molecular Formula: C6H5BrS
• Molecular Weight: 189.076
• Hs Code.: 29309070
• European Community (EC) Number: 203-407-3
• NSC Number: 229563,32018
• UNII: P3WUO03X17
• DSSTox Substance ID: DTXSID8059340
• Nikkaji Number: J365D
• Wikipedia: 4-Bromothiophenol
• Wikidata: Q22829169
• ChEMBL ID: CHEMBL278240
• Mol file: 106-53-6.mol

Synonyms:4-bromothiophenol;p-bromobenzenethiol

Chemical Property of 4-Bromothiophenol

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.0954mmHg at 25°C
• Melting Point: 73-76 °C
• Boiling Point: 231.3 °C at 760 mmHg
• PKA: 6.08±0.10(Predicted)
• Flash Point: 93.7 °C
• PSA: 38.80000
• Density: 1.599 g/cm³
• LogP: 2.73780
• Storage Temp.: Refrigerator
• Water Solubility.: Slightly soluble in water
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 187.92953
• Heavy Atom Count: 8
• Complexity: 66.9

Purity/Quality:

99% ^*data from raw suppliers

4-Bromothiophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TC
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1S)Br
• Uses: 4-Bromothiophenol is a reagent used in the synthesis of indolyl-3-ehtanone-α-thioethers which act as non-toxic antimalrial agents. These compounds show anti-malarial activity, with no toxicity to a HeLa cell line.

Technology Process of 4-Bromothiophenol

There total 94 articles about 4-Bromothiophenol 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: 96.0%

4-bromobenzenesulfonyl chloride (98-58-8) → para-bromobenzenethiol (106-53-6)

Guidance literature:

With sulfuric acid; phosphorus; iodine; In water; at 110 - 140 ℃; for 6h; Inert atmosphere;

DOI:10.1007/s11164-012-0928-8

Reference yield: 92.0%

bis(4-bromophenyl)disulfide (5335-84-2) → para-bromobenzenethiol (106-53-6)

Guidance literature:

With formic acid; 6% Pd/C; at 60 ℃; for 1h;

DOI:10.1080/17415993.2012.654392

Reference yield: 92.0%

Diisopropyl-dithiocarbamic acid 4-bromo-phenyl ester (82884-30-8) → para-bromobenzenethiol (106-53-6)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1016/S0040-4039(00)87244-5

upstream raw materials:

bis(4-aminophenyl)disulfide

S-(4-Bromophenyl)mercapturic acid

bis(4-bromophenyl)disulfide

4-bromobenzenediazonium tetrafluoroborate

Downstream raw materials:

1-benzylsulphanyl-4-bromobenzene

S-p-bromophenyl cyclopropanecarboxylate

2-<<(p-bromophenyl)thio>methyl>pyridine

2-(4-Bromo-phenylsulfanylmethyl)-pyridin-3-ol

Refernces

• 1、 Zhou, Shaodong,Liao, Zutai,Yuan, Jixin,Qian, Chao,Chen, Xinzhi. "One-pot synthesis of 6-bromo-4,4-dimethylthiochroman". . p. 4121 - 4125. Retrieved 2013.
• 2、 Kabilan,Girija,Rajagopal. "Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis". . p. 683 - 688. Retrieved 1999.
• 3、 Bannwart, Linda M.,Mayor, Marcel,Rieder, Pascal S.. "2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group". . p. 4153 - 4164. Retrieved 2019.
• 4、 Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun. "Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol". supporting information. p. 2205 - 2212. Retrieved 2015/07/27.