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Merck
CN

691925

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
NACRES:
NA.23
PubChem Substance ID:
329761448
UNSPSC Code:
12352103
MDL number:
MFCD09907959
Assay:
97%
Form:
liquid

Key Documents

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InChI

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

SMILES string

CCCCCCc1ccsc1Br

InChI key

XQJNXCHDODCAJF-UHFFFAOYSA-N

assay

97%

form

liquid

refractive index

n20/D 1.529

density

1.240 g/mL at 25 °C

Quality Level

200

Related Categories

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

signalword

Danger

hcodes

H301,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000520102
0000520102
0000492969
0000492969
0000458017

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Synthesis and characterization of poly (3-hexylthiophene)-b-polystyrene for photovoltaic application.
Gu Z, et al.
Polymers, 3(1), 558-570 (2011)
Synthesis of End-capped Regioregular Poly (3-hexylthiophene) s via Direct Arylation.
Wang Q, et al.
Macromolecular Rapid Communications, 33(14), 1203-1207 (2012)
Field-effect transistors based on poly (3-hexylthiophene): Effect of impurities.
Urien M, et al.
Organic Electronics, 8(6), 727-734 (2007)
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)
Harsha Reddy et al.
Science (New York, N.Y.), 369(6502), 423-426 (2020-06-06)
Hot carriers in plasmonic nanostructures, generated via plasmon decay, play key roles in applications such as photocatalysis and in photodetectors that circumvent bandgap limitations. However, direct experimental quantification of steady-state energy distributions of hot carriers in nanostructures has so far

Articles

Synthetic Strategy for Large Scale Production of Oligothiophenes

Oligothiophenes are important organic electronic materials which can be produced using synthetic intermediates and Suzuki coupling.

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