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Allyl bromide

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(Redirected from 3-bromopropene)
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.134 Edit this at Wikidata
EC Number
  • 203-446-6
PubChem CID
RTECS number
  • UC7090000
UNII
UN number 1099
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2Key: BHELZAPQIKSEDF-UHFFFAOYSA-N
  • InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H2Key: BHELZAPQIKSEDF-UHFFFAOYAI
SMILES
  • BrCC=C
  • C=CCBr
Properties
Chemical formula C3H5Br
Molar mass 120.977 g·mol
Appearance Clear to light yellow liquid
Odor Unpleasant, irritating, pungent
Density 1.398 g/cm
Melting point −119 °C (−182 °F; 154 K)
Boiling point 71 °C (160 °F; 344 K)
Solubility in water 0.38 g/100 g H2O
log P 1.79
Vapor pressure 18.6 kPa
Magnetic susceptibility (χ) −58.6·10 cm·mol
Refractive index (nD) 1.4697 (20 °C, 589.2 nm)
Viscosity 0.471 cP
Dipole moment ≈1.9 D
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		12.2 kJ·mol (liquid)
45.2 kJ·mol (gas)
Enthalpy of vaporization (ΔfHvap) 32.73 kJ·mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H225, H301, H314, H330, H331, H340, H350, H400
Precautionary statements 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 four-colored diamondHealth 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
Autoignition
temperature 		280 °C (536 °F; 553 K)
Explosive limits 4.3–7.3 %
Threshold limit value (TLV) 0.1 ppm (TWA), 0.2 ppm (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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes 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.

Preparation

Hydrohalogenation

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

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.

Reactions and uses

Allyl bromide is an electrophilic alkylating agent. 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.

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

CH2=CHCH2Br + Mg → CH2=CHCH2MgBr

References

  1. ^ 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. ^ 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.

External links

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