Thiophene, 2-(phenylmethyl)-

Base Information

• Chemical Name: Thiophene, 2-(phenylmethyl)-
• CAS No.: 13132-15-5
• Molecular Formula: C11H10S
• Molecular Weight: 174.266
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20157000
• Nikkaji Number: J81.553E
• Wikidata: Q83025126
• Mol file: 13132-15-5.mol

Synonyms:2-Benzylthiophene;Thiophene, 2-(phenylmethyl)-;13132-15-5;Thiophene, 2-benzyl-;2-benzyl-thiophene;benzyl tiophene;2-(phenylmethyl)thiophene;SCHEMBL45228;DTXSID20157000

Chemical Property of Thiophene, 2-(phenylmethyl)-

Chemical Property:

• Vapor Pressure: 0.0212mmHg at 25°C
• Boiling Point: 259.2°C at 760 mmHg
• Flash Point: 80.1°C
• PSA: 28.24000
• Density: 1.1g/cm³
• LogP: 3.33890
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.05032149
• Heavy Atom Count: 12
• Complexity: 127

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2=CC=CS2

Technology Process of Thiophene, 2-(phenylmethyl)-

There total 49 articles about Thiophene, 2-(phenylmethyl)- 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: 98.0%

thiophene boronic acid (6165-68-0) + benzyl bromide (100-39-0) → 2-benzylthiophene (13132-15-5)

Guidance literature:

With sodium carbonate; trans-PdBr(N-Succ)(PPh₃)2; In tetrahydrofuran; at 60 ℃; for 3h;

DOI:10.1021/ol702291r

Reference yield: 95.0%

thiophene boronic acid (6165-68-0) + benzyl chloride (100-44-7) → 2-benzylthiophene (13132-15-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; at 100 ℃; for 4h; Inert atmosphere; Large scale reaction;

DOI:10.1002/ejoc.200800544

Reference yield: 91.0%

2-Chloromethylthiophene (765-50-4) + phenylboronic acid (98-80-6) → 2-benzylthiophene (13132-15-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-dimethyl-3-(2-phenoxyphenyl)-1-(2,4,6-trimethylbenzyl)imidazolium chloride; caesium carbonate; In 1,4-dioxane; at 90 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo5009178

upstream raw materials:

thiophene

benzyl alcohol

bis(2-thiophenecarbonyl) peroxide

toluene

Downstream raw materials:

ethyl 5-benzyl-ε-oxothiophen-2-hexanoate

5-benzylthiophene-2-carboxaldehyde

5-Benzyl-2-thiophenesulfonyl chloride

methyl 5-benzyl-γ-oxothiophen-2-butanoate

Refernces

• 1、 Srogl, Jiri,Allred, Gary D.,Liebeskind, Lanny S.. "Sulfonium Salts. Participants par Excellence in Metal-Catalyzed Carbon-Carbon Bond-Forming Reactions". . p. 12376 - 12377. Retrieved 1997.
• 2、 Antonietti, Markus,Ghosh, Indrajit,K?nig, Burkhard,Khamrai, Jagadish,Savateev, Aleksandr. "Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst". . p. 3526 - 3532. Retrieved 2020/04/09.
• 3、 Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong. "Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols". supporting information. . Retrieved 2019/05/07.