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691925

Sigma-Aldrich

2-Bromo-3-hexylthiophene

97%

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About This Item

Empirical Formula (Hill Notation):
C10H15BrS
CAS Number:
69249-61-2
Molecular Weight:
247.20
MDL number:
MFCD09907959
UNSPSC Code:
12352103
PubChem Substance ID:
329761448
NACRES:
NA.23

Assay

97%

form

liquid

refractive index

n20/D 1.529

density

1.240 g/mL at 25 °C

SMILES string

CCCCCCc1ccsc1Br

InChI

1S/C10H15BrS/c1-2-3-4-5-6-9-7-8-12-10(9)11/h7-8H,2-6H2,1H3

InChI key

XQJNXCHDODCAJF-UHFFFAOYSA-N

General description

2-Bromo-3-hexylthiophene is a monomeric precursor that forms bromo terminate polymers. It is synthesized by the bromination of hexylthiophene.

Application

2-Bromo-3-hexylthiophene is majorly used in the formation of π-conjugated conductive polymers (CPs) for the fabrication of organic field effect transistors (OFETs) and organic photovoltaics (OPVs). The Grignard metathesis (GRIM) polymerization of 2-Bromo-3-hexylthiophene terminates a bromine and a proton at both ends to form conductive poly(3-hexylthiophene) (P3HT).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5277V
BGBC4397V
BGBB8969
MKBJ6060V
MKBF9098V

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Grignard metathesis (GRIM) polymerization for the synthesis of conjugated block copolymers containing regioregular poly (3-hexylthiophene).
Stefan MC, et al.
Polym. Chem., 3(7), 1693-1701 (2012)
Field-effect transistors based on poly (3-hexylthiophene): Effect of impurities.
Urien M, et al.
Organic Electronics, 8(6), 727-734 (2007)
Synthesis of End-capped Regioregular Poly (3-hexylthiophene) s via Direct Arylation.
Wang Q, et al.
Macromolecular Rapid Communications, 33(14), 1203-1207 (2012)
Synthesis and characterization of poly (3-hexylthiophene)-b-polystyrene for photovoltaic application.
Gu Z, et al.
Polymers, 3(1), 558-570 (2011)

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