3-Bromo-2,2'-bithiophene

Base Information

• Chemical Name: 3-Bromo-2,2'-bithiophene
• CAS No.: 19690-69-8
• Molecular Formula: C8H5BrS2
• Molecular Weight: 245.164
• DSSTox Substance ID: DTXSID10394225
• Nikkaji Number: J1.013.247I
• Wikidata: Q82193493
• Mol file: 19690-69-8.mol

Synonyms:3-bromo-2,2'-bithiophene;19690-69-8;2,2'-Bithiophene, 3-bromo-;Bithiophene, bromo-;bromobithiophene;3-bromo-2-thiophen-2-ylthiophene;SCHEMBL915882;DTXSID10394225;UYEZRRZWTSRZQT-UHFFFAOYSA-N;AKOS025395168;F19575

Chemical Property of 3-Bromo-2,2'-bithiophene

Chemical Property:

• PSA: 56.48000
• LogP: 4.23910
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 243.90161
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

3-Bromo-2,2'-bithiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=C(C=CS2)Br

Technology Process of 3-Bromo-2,2'-bithiophene

There total 7 articles about 3-Bromo-2,2'-bithiophene 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%

2-bromothiophene (1003-09-4) + 2,3-dibromothiophen (3140-93-0) → 3-bromo-[2,2’]bithiophenyl (19690-69-8)

Guidance literature:

2-bromothiophene; With magnesium; In diethyl ether; for 0.75h; Inert atmosphere; Reflux;

2,3-dibromothiophen; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In diethyl ether; at 0 ℃; for 14h; Inert atmosphere;

DOI:10.1039/c4tc02212b

Reference yield: 94.0%

3,5,5’-tribromo-2,2’-bithiophene → 3-bromo-[2,2’]bithiophenyl (19690-69-8)

Guidance literature:

With hydrogenchloride; acetic acid; zinc; In ethanol; water; for 11h; Inert atmosphere; Reflux;

DOI:10.1016/j.polymer.2014.10.048

Reference yield: 89.0%

2,3-dibromothiophen (3140-93-0) + thiophen-2-yl magnesium bromide (5713-61-1) → 3-bromo-[2,2’]bithiophenyl (19690-69-8)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In diethyl ether;

DOI:10.1021/ol402420w

upstream raw materials:

2,3-dibromothiophen

thiophen-2-yl magnesium bromide

thiophene boronic acid

2-bromothiophene

Downstream raw materials:

3,3',5,5'-tetrabromo-2,2'-bithiophene

2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

Refernces

• 1、 -. "NEAR-INFRARED ABSORBING DYE, OPTICAL FILTER, AND IMAGING DEVICE". Paragraph 0163-0164; 0180-0181. . Retrieved 2021/03/13.
• 2、 Scheuble,Gross,Trefz,Brinkmann,López Navarrete,Ruiz Delgado,Ludwigs. "Polythiophenes with Thiophene Side Chain Extensions: Convergent Syntheses and Investigation of Mesoscopic Order". . p. 7049 - 7059. Retrieved 2015/10/28.