Allyl bromide

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]

Allyl bromide
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
EC Number
  • 203-446-6
RTECS number
  • UC7090000
UNII
UN number 1099
  • InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2 Y
    Key: BHELZAPQIKSEDF-UHFFFAOYSA-N Y
  • 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 MSDS at Oxford University
GHS labelling:
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).
Y verify (what is YN ?)
Infobox references

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. 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.


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