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A14022 3-Bromothiophene, 97%

CAS Number
872-31-1
Synonyms
3-Thienyl bromide

Stock No. Size Price ($) Quantity Availability
A14022-09 10g 31.60
A14022-18 50g 123.00
A14022-30 250g 527.00
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3-Bromothiophene, 97%

MDL
MFCD00005464
EINECS
212-821-3

Chemical Properties

Formula
C4H3BrS
Formula Weight
163.04
Boiling Point
157-158°
Flash Point
63°(145°F)
Density
1.722
Refractive Index
1.5910
Storage & Sensitivity
Ambient temperatures.
Solubility
Immiscible with water.

Applications

3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, µ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium.

Notes

Light sensitive. Incompatible with strong oxidizing agents, strong reducing agents and strong bases.

Literature References

Intermediate for preparation of 3-substituted thiophenes by the Grignard route: Arkiv. Kemi., 13, 295 (1959). Similarly, used in the synthesis of poly(3-alkylthiophenes) as conducting polymers: J. Org. Chem., 58, 904 (1993). Conditions have been described for the formation of 3-lithiothiophene, previously considered to be stable only under cryogenic conditions. It has been found to be stable in hexane solution at ambient temperature: Tetrahedron Lett., 35, 3673 (1994). Subsequent reaction with electrophiles leads to a variety of 3-substituted thiophenes.

Tang, T.; Lin, T.; Wang, F.; He, C. Origin of Near-Infrared Absorption for Azulene-Containing Conjugated Polymers upon Protonation or Oxidation. J. Phys. Chem. B 2014, 119 (25), 8176-8183.

Skhiri, A.; Beladhria, A.; Yuan, K.; Soule, J.; Salem, R. B.; Doucet, H. Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzenesulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls. Eur. J. Org. Chem. 2015, 2015 (20), 4428-4436.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H301-H310-H315-H319-H330-H335

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

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-P312-P330-P332+P313-P337+P313-P363-P370+P378q-P50

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. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam

Other References

Beilstein
105338
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2934.99
TSCA
Yes

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