Allyl bromide

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Allyl bromide
Skeletal formula 3-Brompropen.svg
Skeletal formula
Ball-and-stick model Allyl-bromide-3D-balls-B.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-446-6
PubChem CID
RTECS number
  • UC7090000
UNII
UN number 1099
  • InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2 Yes check.svgY
    Key: BHELZAPQIKSEDF-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceClear 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:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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)
NFPA 704.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

  1. 1 2 3 4 5 6 7 8 9 Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2016). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data (2016-2017, 97th ed.). Boca Raton, Florida. ISBN   978-1-4987-5428-6. OCLC   930681942.{{cite book}}: CS1 maint: location missing publisher (link)
  2. ↑ PubChem. "Hazardous Substances Data Bank (HSDB) : 622". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-04.
  3. 1 2 3 4 Yoffe, David; Frim, Ron; Ukeles, Shmuel D.; Dagani, Michael J.; Barda, Henry J.; Benya, Theodore J.; Sanders, David C. (2013). "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–31. doi:10.1002/14356007.a04_405.pub2. ISBN   978-3-527-30385-4.
  4. ↑ Bolton, Roger (2001-04-15), "Allyl Bromide" , in John Wiley & Sons, Ltd (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, pp. ra045, doi:10.1002/047084289x.ra045, ISBN   978-0-471-93623-7 , retrieved 2022-03-04
  5. ↑ Mazerolles, Pierre; Boussaguet, Paul; Huc, Vincent (1999). "6-Chloro-1-Hexene and 8-Chloro-1-Octene" . Organic Syntheses. 76: 221. doi:10.15227/orgsyn.076.0221.
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