3,6-Dibromothieno[3,2-b]thiophene

Base Information

• Chemical Name: 3,6-Dibromothieno[3,2-b]thiophene
• CAS No.: 392662-65-6
• Molecular Formula: C6H2Br2S2
• Molecular Weight: 298.022
• Hs Code.: 2934999090
• European Community (EC) Number: 800-692-1
• DSSTox Substance ID: DTXSID50442557
• Nikkaji Number: J906.514H
• Wikidata: Q72465120
• Mol file: 392662-65-6.mol

Synonyms:3,6-Dibromothieno[3,2-b]thiophene;392662-65-6;3,6-dibromo-thieno[3,2-b]thiophene;Thieno[3,2-b]thiophene, 3,6-dibromo-;3,6-dibromothieno(3,2-b)thiophene;MFCD10000958;NAFCILLINSODIUMSALT;3,6-dibromo-thienothiophene;SCHEMBL1156793;DTXSID50442557;DFMPVYZMICAYCS-UHFFFAOYSA-N;BCP21475;3,6-dibromothieno[3,2,b]thiophene;BBL102860;STL556668;AKOS015901784;CS-W008431;DS-2296;SB13070;AC-22317;SY051420;A6577;AM20100036;D3679;FT-0736934;AU-004/43508419;J-511388

Chemical Property of 3,6-Dibromothieno[3,2-b]thiophene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 127 °C
• Refractive Index: 1.774
• Boiling Point: 332.409 °C at 760 mmHg
• Flash Point: 154.836 °C
• PSA: 56.48000
• Density: 2.21 g/cm³
• LogP: 4.48780
• Storage Temp.: Refrigerator
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 297.79442
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,6-Dibromothieno[3,2-b]thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(S1)C(=CS2)Br)Br

Technology Process of 3,6-Dibromothieno[3,2-b]thiophene

There total 1 articles about 3,6-Dibromothieno[3,2-b]thiophene 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:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 3,6-dibromothiophene[3,2-b]thiophene (392662-65-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 25 - 30 °C / Inert atmosphere; Large scale

2: lithium hydroxide monohydrate / water / 3 h / 100 °C / Inert atmosphere; Large scale

3: bromine; acetic acid / water / 4 h / Inert atmosphere; Reflux; Large scale

4: zinc; acetic acid / 1 h / 110 °C / Large scale

With lithium hydroxide monohydrate; bromine; potassium carbonate; acetic acid; zinc; In water; N,N-dimethyl-formamide;

Reference yield: 91.0%

4-trifluoromethylphenylboronic acid (128796-39-4) + 3,6-dibromothiophene[3,2-b]thiophene (392662-65-6) → 3,6-bis(4-trifluoromethylphenyl)thieno[3,2-b]thiophene (1261434-20-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; for 24h; Reflux;

DOI:10.1246/cl.2011.998

Reference yield: 89.0%

3,6-dibromothiophene[3,2-b]thiophene (392662-65-6) + 2-anilineboronic acid pinacol ester (191171-55-8) → 2,2′-(thieno[3,2-b]thiophene-3,6-diyl)dianiline

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In 1,2-dimethoxyethane; at 90 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.5b01718

upstream raw materials:

3-bromo-2-thiophenecarboxaldehyde

Downstream raw materials:

[(S)-1-((S)-2-{4-[4-(6-bromothieno[3,2-b]thiophen-3-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carbonyl)-2-methylpropyl]carbamic acid methyl ester

(S)-2-{5-[4-(6-bromothieno[3,2-b]thiophen-3-yl)phenyl]-1H-imidazol-2-yl}pyrrolidine-1-carboxylic acid tert-butyl ester

3,6-bis(4-trifluoromethylphenyl)thieno[3,2-b]thiophene

3,6-bis(4-trifluoromethylphenyl)thieno[3,2-b]thiophene-2,5-dione

Refernces