(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)

HCID 288478

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Basic information

CAS: 32281-36-0
Standard SMILES: O=C1c2ccsc2C(=O)c2ccsc21
InChIKey: SIUXRPJYVQQBAF-UHFFFAOYSA-N
Molecular formula: C10H4O2S2
Average molar mass: 220.3 g/mol
Monoisotopic mass: 219.96527137

Names & identifiers

Preferred name: (Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)
IUPAC: thieno[2,3-f][1]benzothiole-4,8-dione
English name: Benzo[1,2-b:4,5-b']dithiophene-4,8-dione
Molecular formula: C10H4O2S2
Molecular weight: 220.27

Names & synonyms

benzo[1,2-b:4,5-b']dithiophene-4,8-dione32281-36-0(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)NSC 149690G1C271HP09NSC-149690UNII-G1C271HP09DTXSID00186030{Benzo[1,2-b:4,5-b]dithiophene-4,8-dione}BENZO(1,2-B:4,5-B')DITHIOPHENE-4,8-DIONE4,8-DIHYDROBENZO(1,2-B:4,5-B')DITHIOPHENE-4,8-DIONE4,10-dithiatricyclo[7.3.0.0^3,7^]dodeca-1(9),3(7),5,11-tetraene-2,8-dione

Show more names

BDTONAILNmrkLy-90SLAMF44,5-b']dithiophene-4,8-dione

4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione4,10-dithiatricyclo(7.3.0.0^3,7^)dodeca-1(9),3(7),5,11-tetraene-2,8-dioneRefChem:69873DTXCID10108521thieno[2,3-f][1]benzothiole-4,8-dioneMFCD01927240thieno[2,3-f]benzothiophene-4,8-dioneNSC149690

Database identifiers

CAS: 32281-36-0
PubChem CID: 288478
DTXSID: DTXSID00186030
ChEMBL: CHEMBL358186
UNII: G1C271HP09
Nikkaji: J633.591H

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 90.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 272

Physicochemical properties

Melting point: 260 · 260-262℃
Boiling point: 408 · 408.0±35.0 °C(Predicted)
Density: 1.595 · 1.595
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: powder to crystal
color: White to Amber to Dark green
InChI: InChI=1S/C10H4O2S2/c11-7-5-1-3-13-9(5)8(12)6-2-4-14-10(6)7/h1-4H
InChIKey: SIUXRPJYVQQBAF-UHFFFAOYSA-N
SMILES: C12C(=O)C3C=CSC=3C(=O)C=1C=CS2
FDA UNII: 1 C271HP09 · G1C271HP09
UNSPSC Code: 12352103 · 12352103
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 280 · P280-P302+P352-P362+P364
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

wgk: 3
hs_code: 29349990
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P280-P302+P352-P362+P364

Chemistry & industry

Applications · 4 items

DescriptionBenzo[1,2-b:4,5-b’]dithiophene is a planar symmetrical molecular structure of the thiophene derivative, enabling a better π-πstacking and good electron delocalization that encourages charge transport. In recent years, it has been intensively studied for the application of OFETs and OPVs. The incorporation of a low-band-gap unit into the benzo[1,2-b:4,5-b’]dithiophene unit could potentially result in a red-shifted absorption due to its electron-rich properties. Benzo[1,2-b:4,5-b’]dithiophene can be chemically modified to fine-tune its chemical structure and electron properties (e.g. band gap), energy levels, and charge mobility of the small molecule/polymers of interest (at a molecular level).

Usessuzuki reaction

UsesBDTD can be used as an acceptor layer in the fabrication of polymer based solar cells.

General DescriptionBenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (BDTD) is a conductive polymer with a symmetric and planar conjugated structure which has a hole mobility of 0.25 cm2V-1s-1.