Allyl bromide

Quality 0.50 · 2 views · Updated 2 months ago

title: "Allyl bromide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["bromoalkenes", "allyl-compounds"] topic_path: "general/bromoalkenes" source: "https://en.wikipedia.org/wiki/Allyl_bromide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477314323 | ImageFile = 3-Brompropen.svg | ImageSize = 180px | ImageName = Skeletal formula | ImageFile1 = Allyl-bromide-3D-balls-B.png | ImageName1 = Ball-and-stick model | PIN = 3-Bromoprop-1-ene | OtherNames = Allyl bromide 3-Bromopropene 3-Bromopropylene 3-Bromo-1-propene Bromoallylene 2-Propenyl bromide |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 7553 | InChIKey = BHELZAPQIKSEDF-UHFFFAOYAI | SMILES1 = C=CCBr | StdInChI_Ref = | StdInChI = 1S/C3H5Br/c1-2-3-4/h2H,1,3H2 | StdInChIKey_Ref = | StdInChIKey = BHELZAPQIKSEDF-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 106-95-6 | UNII_Ref = | UNII = FXQ8X2F74Z | EINECS = 203-446-6 | PubChem = 7841 | SMILES = BrCC=C | InChI = 1/C3H5Br/c1-2-3-4/h2H,1,3H2 | RTECS = UC7090000 | UNNumber = 1099 |Section2={{Chembox Properties | C=3|H=5|Br=1 | Appearance = Clear to light yellow liquid | Odor = Unpleasant, irritating, pungent | Density = 1.398 g/cm3 | MeltingPtC = −119 | MeltingPt_notes = | BoilingPtC = 71 | BoilingPt_notes = | Solubility = 0.38 g/100 g H2O | RefractIndex = 1.4697 (20 °C, 589.2 nm) | MagSus = −58.6·10−6 cm3·mol−1 | LogP = 1.79 | Viscosity = 0.471 cP | VaporPressure = 18.6 kPa | Dipole = ≈1.9 D | Section4 = {{Chembox Thermochemistry | DeltaHform = 12.2 kJ·mol−1 (liquid) 45.2 kJ·mol−1 (gas) | DeltaHvap = 32.73 kJ·mol−1 |Section7={{Chembox Hazards | ExternalSDS = MSDS at Oxford University | MainHazards = | FlashPt = −2 to −1 °C | AutoignitionPtC = 280 | NFPA-H = 3 | NFPA-F = 3 | NFPA-R = 1 | NFPA-S = | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | ExploLimits = 4.3–7.3 % | TLV-TWA = 0.1 ppm | TLV-STEL = 0.2 ppm | Section8 = {{Chembox Related | OtherCompounds = Allyl chloride Allyl iodide

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

References

  1. (2016). "CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data.".
  2. PubChem. "Hazardous Substances Data Bank (HSDB) : 622".
  3. (2013). "Ullmann's Encyclopedia of Industrial Chemistry".
  4. Bolton, Roger. (2001-04-15). "Allyl Bromide". John Wiley & Sons, Ltd.
  5. (1999). "6-Chloro-1-Hexene and 8-Chloro-1-Octene". Organic Syntheses.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

bromoalkenesallyl-compounds