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1003-09-4 - 2-Bromothiophene, 98+% - 2-Thienyl bromide - A11959 - Alfa Aesar

A11959 2-Bromothiophene, 98+%

CAS Number
1003-09-4
Synonyms
2-Thienyl bromide

2-Bromothiophene, 98+%

MDL
MFCD00005417
EINECS
213-699-4

Chemical Properties

Formula
C4H3BrS
Formula Weight
163.04
Melting point
<-10°
Boiling Point
149-152°
Flash Point
58°(136°F)
Density
1.701
Refractive Index
1.5860
Sensitivity
Light Sensitive
Solubility
Not miscible or difficult to mix in water.

Applications

2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis.

Notes

Light Sensitive. Keep away from oxidizing agents. Store in dark.

Literature References

Mubarak MS and Peters DG. Electrochemical Reduction of Mono- and Dihalothiophenes at Carbon Cathodes in Dimethylformamide. First Example of an Electrolytically Induced Halogen Dance.J. Org. Chem.,1996,61(23), 8074-8078.

Peyron C, et al. First example of base-promoted tandem alkylation-bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect.Tetrahedron Lett.2005,46(19), 3315-3318.

Sathyapalan A, et al. Novel self assembled monolayers of allyl phenyl thiophene ether as potential dielectric material for organic thin film transistors.Thin Solid Films,2008,516(16), 5645-5648.

The bromo-substituent can be readily displaced by methoxide in methanol in the presence of a Cu(I) catalyst: Synth. Commun., 20, 213 (1990). For coupling reaction with Thiophene-2-thiol, B22642, in the presence of Cu2O, to give 2,2'-dithienyl sulfide, see: Org. Synth. Coll., 6, 558 (1988).

Allylic alcohols are thienylated by means of a Heck-type, Pd-catalyzed coupling reaction; the products are ketones formed by rearrangement: Chem. Lett., 423 (1977). Coupling with iodoarenes can be induced at the 5-position by the use of a palladium(II) catalyst in the presence of silver nitrate and potassium fluoride, providing access to 5-aryl-2-bromothiophene derivatives, which may be further elaborated by reaction with the available 2-bromo-substituent: Org. Lett., 7, 5083 (2005).

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H300-H310-H330-H315-H319

Flammable liquid and vapour. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P260u-P201-P280a-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
104663
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2934.99
TSCA
Yes

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