2,5-Dibromothieno[3,2-b]thiophene

Base Information

• Chemical Name: 2,5-Dibromothieno[3,2-b]thiophene
• CAS No.: 25121-87-3
• Molecular Formula: C6H2Br2S2
• Molecular Weight: 298.022
• Hs Code.: 29349990
• European Community (EC) Number: 687-363-4
• DSSTox Substance ID: DTXSID60394013
• Nikkaji Number: J88.320D
• Wikidata: Q72465117
• Mol file: 25121-87-3.mol

Synonyms:2,5-Dibromothieno[3,2-b]thiophene;25121-87-3;2,5-DIBROMO-THIENO[3,2-B]THIOPHENE;Thieno[3,2-b]thiophene, 2,5-dibromo-;SCHEMBL144144;YSSJ00753;DTXSID60394013;APDAUBNBDJUQGW-UHFFFAOYSA-N;BCP02739;BBL102895;MFCD03931293;STL556704;AKOS015898694;AB93054;DS-1531;PS-4008;AC-22784;2,5-Dibromothieno[3,2-b]thiophene, 97%;A5096;AM20090292;CS-0006084;D3678;FT-0685617;W-202054

Chemical Property of 2,5-Dibromothieno[3,2-b]thiophene

Chemical Property:

• Vapor Pressure: 0.000113mmHg at 25°C
• Melting Point: 130 °C
• Refractive Index: 1.773
• Boiling Point: 346.695 °C at 760 mmHg
• Flash Point: 163.475 °C
• PSA: 56.48000
• Density: 2.21 g/cm³
• LogP: 4.48780
• Storage Temp.: Refrigerator
• XLogP3: 4.8
• 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:

97% ^*data from raw suppliers

2,5-Dibromothieno[3,2-b]thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC2=C1SC(=C2)Br)Br
• Uses: 2,5-Dibromothieno[3,2-b]thiophene is useful in preparation and electronic properties of fused oligothienoacenes.

Technology Process of 2,5-Dibromothieno[3,2-b]thiophene

There total 2 articles about 2,5-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: 99.0%

thieno[3,2-b]thiophene (251-41-2) → 2,5-dibromothieno[3,2-b]thiophene (25121-87-3)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 2,5-dibromothieno[3,2-b]thiophene (25121-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide

2: sodium hydroxide

3: copper; quinoline

4: N-Bromosuccinimide / N,N-dimethyl-formamide

With quinoline; N-Bromosuccinimide; copper; potassium carbonate; sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.3390/molecules171012163

Reference yield: 87.0%

4-(diphenylamino)phenylboronic pinacol ester (267221-88-5) + 2,5-dibromothieno[3,2-b]thiophene (25121-87-3) → 4,4'-(thieno[3,2-b]thiophene-2,5-diyl)bis[(N,N-diphenyl)benzenamine]

Guidance literature:

With (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II); potassium tert-butylate; In water; isopropyl alcohol; for 2h; Reflux; Inert atmosphere;

DOI:10.1002/cphc.201601204

upstream raw materials:

thieno[3,2-b]thiophene

3-bromo-2-thiophenecarboxaldehyde

Downstream raw materials:

2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene

2,5-bis[2-(trimethylsilyl)ethynyl]thieno[3,2-b]thiophene

Thieno<3,2-b>thiophen-2,5-dion

trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane