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2-bromo-3-hexylthiophene

2-bromo-3-hexylthiophene structure

CAS No:
69249-61-2
Formula:
C10H15BrS
Chemical Name:
2-bromo-3-hexylthiophene
Synonyms:
2-bromo-3-hexylthiophene;2-Bromo-3-nonylthiophene;TH6-Bra;Thiophene,2-broMo-3-hexyl-;2-Bromo-3-hexylthiophene 97%;2-Bromo-3-hexyL;2-Bromo-3-hexylthiophene >;2-bromo-3-hexylthiophene ISO 9001：2015 REACH
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Colorless to yellow liquid

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

2-bromo-3-hexylthiophene Basic Attributes

Molecular Weight：

247.2

Exact Mass：

246.007782

DSSTox ID：

DTXSID20449876

Color/Form：

Colorless to Light yellow to Light orange

HScode：

29349990

Characteristics

PSA：

28.2

XLogP3：

5.6

Density：

1.240 g/mL at 25 °C

Boiling Point：

75°C/0.5mmHg(lit.)

Flash Point：

110 °C

Refractive Index：

n20/D 1.529

Water Solubility：

Slightly miscible with water.

Storage Conditions：

0-10°C

Critical Temperature & Pressure：

Keep in dark place,Sealed in dry,Room Temperature

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1

Transport codes：

UN28106.1/PG3

wgk germany：

hazard class code：

safety instructions：

Marks：

Precautionary statement(s)：

P301 + P310-P305 + P351 + P338

Hazard Statements：

RIDADR：

UN 2810 6.1/PG 3

GHS Classification：

|Danger|H301 (95%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-bromo-3-hexylthiophene

2-bromo-3-hexylthiophene Use and Manufacturing

Methods of Manufacturing

A 1 M solution of compound 8a in DMF was cooled to 0 °C in the absence of light and NBS (1.0 eq.) was added. The mixture was allowed to warm to room temperature, stirred overnight and then diluted with DCM . The solution was extracted with HFirst, 2-bromo-3-hexylthiophene was synthesized via the reaction of 3-hexylthiophene with N-bromosuccinimide (NBS). To a flask equipped with magnetic stirrer, 3-hexylthiophene (10.000 g, 59.4 mmol) and THF (100 mL) were charged with vigorous stirring and then NBS (10.580 g, 59.4 mmol) was added at 0 °C. The reaction was carried out at 0 °C for 2 h and then 100 mL of deionized water was added. The organic layer was extracted out with diethyl ether and the organic layer was successively washed with 10percent aqueous solutions of Na2-Bromo-3-hexylthiophene was prepared similarly to a method described by Carlsen et al.10 and was modified as follows: 3-hexylthiophene (12.0 g, 71.3 mmol) was dissolved in glacial acetic acid (100 mL) under an air atmosphere. Then NBS (12.7 g, 71.5 mmol) was added in one portion. The reaction mixture was stirred for 2.5 h at 22 °C. Then the solution was poured into water (200 mL) and diethyl ether (250 mL). After extraction, the organic phase was separated and washed with aqueous NaOH (2 M, 5 x 150 mL), followed by water (3 x 150 mL). The organic layer was dried over MgSO4 and then the solvent was removed in vacuo. The crude product was purified by vigreux distillation (130 °C, 4 x 10-2 mbar) to receive 13.5 g (77percent, lit.10 92percent) of light yellow oil.

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.

Computed Properties

Molecular Weight:247.20
XLogP3:5.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:246.00778
Monoisotopic Mass:246.00778
Topological Polar Surface Area:28.2
Heavy Atom Count:12
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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