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A11959 2-Bromothiophene, 98+%

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

Stock No. Size Price ($) Quantity Availability
A11959-18 50g 40.00
A11959-30 250g 114.00
A11959-0B 1000g 421.00
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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
Storage & Sensitivity
Light Sensitive. Ambient temperatures.
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-H315-H318-H330

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

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P262-P264b-P270-P271-P280-P284-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P332+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. 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. Rinse mouth. If skin irritation occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

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