2-(S-Ethylthiomethyl)-1-bromobenzene

Base Information

• Chemical Name: 2-(S-Ethylthiomethyl)-1-bromobenzene
• CAS No.: 99180-11-7
• Molecular Formula: C9H11BrS
• Molecular Weight: 231.156
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID80445415
• Nikkaji Number: J3.599.496C
• Mol file: 99180-11-7.mol

Synonyms:2-(S-Ethylthiomethyl)-1-bromobenzene;99180-11-7;1-bromo-2-(ethylsulfanylmethyl)benzene;(2-Bromobenzyl)(ethyl)sulfane;2-Bromobenzylethyl sulfide;DTXSID80445415;ZDA18011;MFCD14644600;AKOS008951131;2-(S-ethyl thiomethyl)-1-bromobenzene;1-bromo-2-[(ethylsulfanyl)methyl]benzene;BS-24846;CS-0208556;J3.599.496C

Chemical Property of 2-(S-Ethylthiomethyl)-1-bromobenzene

Chemical Property:

• PSA: 25.30000
• LogP: 3.70220
• Storage Temp.: Room temperature.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 229.97648
• Heavy Atom Count: 11
• Complexity: 106

Purity/Quality:

95% ^*data from raw suppliers

2-(S-Ethylthiomethyl)-1-bromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSCC1=CC=CC=C1Br

Technology Process of 2-(S-Ethylthiomethyl)-1-bromobenzene

There total 4 articles about 2-(S-Ethylthiomethyl)-1-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: 95.0%

ethanethiol (75-08-1) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → 2-<(ethylthio)methyl>bromobenzene (99180-11-7)

Guidance literature:

ethanethiol; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

1-Bromo-2-bromomethyl-benzene; In tetrahydrofuran; for 16h; Reflux;

DOI:10.1021/acs.joc.5b00378

Reference yield: 90.0%

[(2-bromophenyl)methylene]bis(ethylsulfane) → 2-<(ethylthio)methyl>bromobenzene (99180-11-7)

Guidance literature:

[(2-bromophenyl)methylene]bis(ethylsulfane); With chloro-trimethyl-silane; sodium iodide; In dichloromethane; at 35 ℃; for 20h; Inert atmosphere; Green chemistry;

With water; In dichloromethane; at 20 ℃; Inert atmosphere; Green chemistry;

DOI:10.1002/adsc.201800437

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → 2-<(ethylthio)methyl>bromobenzene (99180-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 20 °C / Inert atmosphere

2.1: sodium iodide; chloro-trimethyl-silane / dichloromethane / 20 h / 35 °C / Inert atmosphere; Green chemistry

2.2: 20 °C / Inert atmosphere; Green chemistry

With chloro-trimethyl-silane; boron trifluoride diethyl etherate; sodium iodide; In dichloromethane;

DOI:10.1002/adsc.201800437

upstream raw materials:

sodium thioethylate

1-Bromo-2-bromomethyl-benzene

ethanethiol

ortho-bromobenzaldehyde

Downstream raw materials:

2-(2-ethylsulfanylmethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(2-(ethylthiomethyl)phenyl)-1,3,2-dioxaborolane

9-{2-(ethylthiomethyl)phenyl}-9-borabicyclo{3.3.1}nonane

9-{2-(1-ethylthiopentyl)phenyl}-9-borabicyclo{3.3.1}nonane

Refernces

• 1、 Zhao, Guangkuan,Yuan, Ling-Zhi,Alami, Mouad,Provot, Olivier. "Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions". . p. 2522 - 2536. Retrieved 2018/05/14.
• 2、 Rohde, Volker H. G.,Müller, Maria F.,Oestreich, Martin. "Intramolecularly Sulfur-Stabilized Silicon Cations with Chiral Binaphthyl Backbones: Synthesis of Three Different Motifs and Their Application in Enantioselective Diels-Alder Reactions". . p. 3358 - 3373. Retrieved 2016/01/15.