2-(Trifluoromethylthio)bromobenzene

Base Information

• Chemical Name: 2-(Trifluoromethylthio)bromobenzene
• CAS No.: 1644-72-0
• Molecular Formula: C7H4BrF3S
• Molecular Weight: 257.074
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID50381396
• Nikkaji Number: J785.119G
• Wikidata: Q72513071
• Mol file: 1644-72-0.mol

Synonyms:1644-72-0;2-(Trifluoromethylthio)bromobenzene;1-Bromo-2-(Trifluoromethylthio)Benzene;1-bromo-2-(trifluoromethylsulfanyl)benzene;(2-bromophenyl)(trifluoromethyl)sulfane;2-Bromophenyl trifluoromethyl sulphide;1-bromo-2-[(trifluoromethyl)sulfanyl]benzene;MFCD00236347;2-BROMOPHENYL TRIFLUOROMETHYL SULFIDE;SCHEMBL3831544;DTXSID50381396;IWRJVJJQWGZKMT-UHFFFAOYSA-N;BBL100879;STL554673;AKOS005063447;1-(Trifluoromethylthio)-2-bromobenzene;MS-20094;2-BROMOPHENYLTRIFLUOROMETHYLSULPHIDE98;CS-0447778;FT-0611595;2-BROMOPHENYL TRIFLUOROMETHYL SULPHIDE 98;1-Bromo-2-(trifluoromethylthio)benzene, AldrichCPR;J-500670

Chemical Property of 2-(Trifluoromethylthio)bromobenzene

Chemical Property:

• Vapor Pressure: 3.88mmHg at 25°C
• Refractive Index: 1.547
• Boiling Point: 155.581 °C at 760 mmHg
• Flash Point: 47.894 °C
• PSA: 25.30000
• Density: 1.717 g/cm³
• LogP: 4.06100
• Sensitive.: Stench
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 255.91692
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

99% ^*data from raw suppliers

2-(Trifluoromethylthio)bromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)SC(F)(F)F)Br
• Uses: 1-Bromo-2-(trifluoromethylthio)benzene is used as organic chemical synthesis intermediate. It is also a useful halogenated compound for proteomics research.

Technology Process of 2-(Trifluoromethylthio)bromobenzene

There total 14 articles about 2-(Trifluoromethylthio)bromobenzene 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: 93.0%

N-((trifluoromethyl)thio)isoindoline-1,3-dione (719-98-2) + (2-bromophenyl)boronic acid (244205-40-1) → 1-bromo-2-[(trifluoromethyl)sulfanyl]benzene (1644-72-0)

Guidance literature:

With [2,2]bipyridinyl; potassium carbonate; copper(l) chloride; In 1,2-dimethoxyethane; at 45 ℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201307484

Reference yield: 65.0%

1-bromo-2-{[bromo(difluoro)methyl]sulfanyl}benzene (1395062-33-5) → 1-bromo-2-[(trifluoromethyl)sulfanyl]benzene (1644-72-0)

Guidance literature:

With silver tetrafluoroborate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/anie.201504665

Reference yield: 62.0%

iodotrifluoromethane (2314-97-8,263005-66-9) + o-bromothiophenol (6320-02-1) → 1-bromo-2-[(trifluoromethyl)sulfanyl]benzene (1644-72-0)

Guidance literature:

o-bromothiophenol; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

iodotrifluoromethane; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1016/j.jfluchem.2011.07.008

upstream raw materials:

bis(2-bromophenyl) disulfide

potassium trifluoroacetate

bromobenzene

Trifluoromethylsulfenyl chloride

Downstream raw materials:

1-(trifluoromethylsulfanyl)-2-vinylbenzene

1-bromo-4-nitro-2-(trifluoromethylthio)benzene

Refernces

• 1、 Zhu, Xing-Xing,Wang, Huai-Qin,Li, Chen-Guang,Xu, Xiao-Lan,Xu, Jun,Dai, Jian-Jun,Xu, Hua-Jian. "Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate". . p. 16114 - 16120. Retrieved 2021.
• 2、 Krishanmoorthy, Sankarganesh,Schnell, Simon D.,Dang, Huong,Fu, Fang,Prakash, G.K. Surya. "Fluorodecarboxylation: Synthesis of aryl trifluoromethyl ethers (ArOCF3) and thioethers (ArSCF3)". . p. 130 - 135. Retrieved 2017/09/06.