Allyl bromide

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Allyl bromide
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
3-Bromoprop-1-ene
Other names
Allyl bromide
3-Bromopropene
3-Bromopropylene
3-Bromo-1-propene
Bromoallylene
2-Propenyl bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.134 Edit this at Wikidata
EC Number
  • 203-446-6
RTECS number
  • UC7090000
UNII
UN number 1099
  • InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2 checkY
    Key: BHELZAPQIKSEDF-UHFFFAOYSA-N checkY
  • InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H2
    Key: BHELZAPQIKSEDF-UHFFFAOYAI
  • BrCC=C
  • C=CCBr
Properties
C3H5Br
Molar mass 120.977 g·mol−1
Appearance Clear to light yellow liquid
Density 1.398 g/cm3
Melting point −119 °C (−182 °F; 154 K)
Boiling point 71 °C (160 °F; 344 K)
Very slightly soluble
1.4697 (20 °C, 589.2 nm)
Hazards
Safety data sheet (SDS) MSDS at Oxford University
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word
 Danger
H225, H301, H314, H330, H331, H340, H350, H400
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P320, P321, P330, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
3
3
1
Flash point −2 to −1 °C
280 °C (536 °F; 553 K)
Explosive limits 4.3–7.3 %
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  (what is checkY☒N ?)
Infobox references

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, and other organic compounds. Physically, allyl bromide is a colorless liquid with an intense, acrid, and persistent smell. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.[1]

Synthesis and reactions[]

It is produced commercially from allyl alcohol. Alternatively allyl chloride reacts with hydrogen bromide in the presence of copper bromide.[1]

The compound is mainly used as an electrophilic allylating agent.[2] Allylzinc bromide may be produced by treating this compound with elemental zinc.

See also[]

References[]

  1. ^ a b Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.
  2. ^ José C. González-Gómez; Francisco Foubelo; Miguel Yus (2012). "Preparation of Enantioenriched Homoallylic Primary Amines". Org. Synth. 89: 88. doi:10.15227/orgsyn.089.0088.

External links[]


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