2-bromo-3-hexylthiophene Chemical Properties

Boiling point:

75°C/0.5mmHg(lit.)

Density 

1.240 g/mL at 25 °C

refractive index 

n20/D 1.529

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

Slightly miscible with water.

InChI

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

InChIKey

XQJNXCHDODCAJF-UHFFFAOYSA-N

SMILES

C1(Br)SC=CC=1CCCCCC

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29349990

2-bromo-3-hexylthiophene Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

2-Bromo-3-hexylthiophene is used in the synthesis of End-capped Regioregular Poly(3-hexylthiophene). It is also used to synthesize well-defined head-to-tail-type oligothiophenes which are used in a number of high-technology applications including OLEDs.

General Description

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

Synthesis

General procedure for the synthesis of 2-bromo-3-hexylthiophene from 3-hexylthiophene: A 1 M solution of 3-hexylthiophene (8a) in DMF was cooled to 0 °C under light-avoidance conditions, followed by the addition of N-bromosuccinimide (NBS, 1.0 equiv). The reaction mixture was slowly warmed to room temperature with continuous stirring overnight. After completion of the reaction, the reaction solution was diluted with dichloromethane (DCM). The organic phase was washed sequentially with water and brine, the aqueous phase was combined and back-extracted with DCM. All organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: petroleum ether) to afford 2-bromo-3-hexylthiophene (7a) as a colorless oil in 99% yield.1H NMR (300.13 MHz, CDCl3) δ (ppm): 7.18 (d, 3J = 5.5 Hz, 1H, H-9), 6.79 (d, 3J = 5.5 Hz, 1H, H-8). 2.56 (t, 3J = 7.7 Hz, 2H, H-6), 1.63-1.51 (m, 2H, H-5), 1.40-1.24 (m, 6H, H-4 to H-2), 0.89 (t, 3J = 6.8 Hz, 3H, H-1).

References

[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1752 - 1763
[2] Patent: WO2015/15397, 2015, A1. Location in patent: Page/Page column 50
[3] Chemistry - A European Journal, 2014, vol. 20, # 49, p. 16128 - 16137
[4] Journal of Materials Chemistry, 2011, vol. 21, # 5, p. 1462 - 1469
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 9, p. 1933 - 1941

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