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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

Size Price ($) Quantity Availability
50g 34.32
250g 114.75
1000g 326.40
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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: H300-H310-H330-H315-H319-H226

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

Precautionary Statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. 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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