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Allyl bromide

Chemical compound From Wikipedia, the free encyclopedia

Allyl bromide

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes[2] and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.[3]

Quick Facts Names, Identifiers ...
Allyl bromide
Thumb
Skeletal formula
Thumb
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
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
Odor Unpleasant, irritating, pungent
Density 1.398 g/cm3
Melting point −119 °C (−182 °F; 154 K)
Boiling point 71 °C (160 °F; 344 K)
0.38 g/100 g H2O [1]
log P 1.79[1]
Vapor pressure 18.6 kPa
−58.6·10−6 cm3·mol−1[1]
1.4697 (20 °C, 589.2 nm)
Viscosity 0.471 cP[1]
≈1.9 D[1]
Thermochemistry
12.2 kJ·mol−1 (liquid)
45.2 kJ·mol−1 (gas)[1]
32.73 kJ·mol−1[1]
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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)
ThumbHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
Flash point −2 to −1 °C
280 °C (536 °F; 553 K)
Explosive limits 4.3–7.3 %
0.1 ppm[1] (TWA), 0.2 ppm[1] (STEL)
Safety data sheet (SDS) MSDS at Oxford University
Related compounds
Related compounds
 Allyl chloride
Allyl iodide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation

Hydrohalogenation

Allyl bromide is produced commercially from allyl alcohol and hydrobromic acid:[3]

CH2=CHCH2OH + HBr → CH2=CHCH2Br + H2O

It can also be prepared by the halogen-exchange reaction between allyl chloride and hydrobromic acid or by the allylic bromination of propene.[3]

Reactions and uses

Allyl bromide is an electrophilic alkylating agent.[4] It reacts with nucleophiles, such as amines, carbanions, alkoxides, etc., to introduce the allyl group:

CH2=CHCH2Br + Nu− → CH2=CHCH2Nu + Br− (Nu− is a nucleophile)

It is used in the synthesis of compounds containing the allyl functionality, such as the pharmaceuticals methohexital, secobarbital and thiamylal.[3]

Allyl bromide reacts with magnesium metal in dry ether to form allylmagnesium bromide, a Grignard reagent:[5]

CH2=CHCH2Br + Mg → CH2=CHCH2MgBr

References

External links

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