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

A11959 2-Bromothiophene, 98+%

Numéro de CAS
1003-09-4
Synonymes
2-Thienyl bromide

Conditionnement Prix ($) Quantité Disponibilité
50g 38,70
250g 121,00
1000g 404,00
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2-Bromothiophene, 98+%

MDL
MFCD00005417
EINECS
213-699-4

Propriétés chimiques

Formule
C4H3BrS
Poids moleculaire
163.04
Point de fusion
<-10°
Point d'ébullition
149-152°
Point d'éclair
58°(136°F)
Densité
1.701
Indice de réfraction
1.5860
Sensibilité
Light Sensitive
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): 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.

Mentions de prudence: P301+P310a-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a

IF SWALLOWED: 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.

Autres références

Beilstein
104663
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2934.99
TSCA
Yes

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