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Allyl bromide information


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
  • 106-95-6 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 7553 checkY
ECHA InfoCard 100.003.134 Edit this at Wikidata
EC Number
  • 203-446-6
PubChem CID
  • 7841
RTECS number
  • UC7090000
UNII
  • FXQ8X2F74Z checkY
UN number 1099
CompTox Dashboard (EPA)
  • DTXSID8024442 Edit this at Wikidata
InChI
  • InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2 checkY
    Key: BHELZAPQIKSEDF-UHFFFAOYSA-N checkY
  • InChI=1/C3H5Br/c1-2-3-4/h2H,1,3H2
    Key: BHELZAPQIKSEDF-UHFFFAOYAI
SMILES
  • BrCC=C
  • C=CCBr
Properties
Chemical formula
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)
Solubility in water
0.38 g/100 g H2O [1]
log P 1.79[1]
Vapor pressure 18.6 kPa
Magnetic susceptibility (χ)
−58.6·10−6 cm3·mol−1[1]
Refractive index (nD)
1.4697 (20 °C, 589.2 nm)
Viscosity 0.471 cP[1]
Dipole moment
≈1.9 D[1]
Thermochemistry
Std enthalpy of
formation fH298)
12.2 kJ·mol−1 (liquid)
45.2 kJ·mol−1 (gas)[1]
Enthalpy of vaporization fHvap)
32.73 kJ·mol−1[1]
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[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).
checkY verify (what is checkY☒N ?)
Infobox references

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]

  1. ^ a b c d e f g h i CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (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.

and 24 Related for: Allyl bromide information

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Allyl bromide

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

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Hydrogen bromide

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stronger acid (HBr) and release of the weaker acid (HCl). Allyl bromide is prepared by treating allyl alcohol with HBr: CH2=CHCH2OH + HBr → CH2=CHCH2Br + H2O...

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Allyl chloride

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Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision. Allyl Allyl bromide Allyl iodide...

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Allyl alcohol

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commercial synthesis of allyl bromide: CH2=CHCH2OH + HBr → CH2=CHCH2Br + H2O Allyl alcohol is hepatotoxic. In rats, in vivo, allyl alcohol is metabolized...

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Allyl cyanide

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obtained by the reaction of allyl acetate with hydrogen cyanide. A laboratory route to allyl cyanide involves treating allyl bromide with copper(I) cyanide...

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Allylmagnesium bromide

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Allylmagnesium bromide is a Grignard reagent used for introducing the allyl group. It is commonly available as a solution in diethyl ether. It may be synthesized...

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Allyl halide

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Allyl halides are organic halides containing an allyl group. Allyl halides include: Allyl chloride Allyl bromide Allyl iodide Allyl fluoride [Wikidata]...

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Organobromine chemistry

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of allyl bromide: HOCH2CH=CH2 + HBr → BrCH2CH=CH2 + H2O Methyl bromide, another fumigant, is generated from methanol and hydrogen bromide. Bromide ions...

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Allyl phenyl ether

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Allyl phenyl ether is prepared by the reaction of sodium phenoxide with allyl bromide: C6H5ONa + BrCH2CH=CH2 → C6H5OCH2CH=CH2 + NaBr The yield is almost quantitative...

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Vinyl bromide

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Group 2A carcinogens as a suspected human carcinogen. Vinyl chloride Allyl bromide Bromoethane NIOSH Pocket Guide to Chemical Hazards. "#0657". National...

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Hydrobromic acid

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significant organic compounds prepared from hydrobromic acid include allyl bromide, tetrabromobis(phenol), and bromoacetic acid. HBr almost uniquely participates...

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Carvone

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stereoselectivity. The resulting enolate can then be allylated using allyl bromide to give ketone 11. In the body, in vivo studies indicate that both enantiomers...

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Allyl iodide

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before decomposition into free iodine becomes apparent. Allyl Allyl alcohol Allyl bromide Allyl chloride Bertleff, Werner (2000). "Carbonylation". Ullmann's...

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Rocuronium bromide

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Rocuronium bromide (brand names Zemuron, Esmeron) is an aminosteroid non-depolarizing neuromuscular blocker or muscle relaxant used in modern anaesthesia...

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Propargyl bromide

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bromide, i.e., CH2=C=CHMgBr. Propargyl bromide is a lachrymator and an alkylating agent. Propargyl Propargyl chloride Propargyl alcohol Allyl bromide...

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Allyl isothiocyanate

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Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous...

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Muscarine

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ether gives the aldehyde (4). Treatment of the crude aldehyde with allyl bromide and zinc powder in water with NH4Cl as catalyst resulted in an anti:syn...

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Safrole

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conversion to methylenedioxybenzene, which is brominated and coupled with allyl bromide. Safrole is a versatile precursor to many compounds. Examples are N-acylarylhydrazones...

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Wender Taxol total synthesis

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preparation of Taxol by this route include verbenone, prenyl bromine, allyl bromide, propiolic acid, Gilman reagent, and Eschenmoser's salt. The taxol synthesis...

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Carbonyldiimidazole

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treated with at least 3 equivalents of an activated halide (such as allyl bromide or iodomethane) and CDI yields the corresponding halide with good yield...

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Allylic rearrangement

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3-methyl-2-buten-1-ol is 15%. Allylic shifts occur because the transition state is an allyl intermediate. In other respects they are similar to classical nucleophilic...

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C3H5Br

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The molecular formula C3H5Br may refer to: Allyl bromide Bromocyclopropane This set index page lists chemical structure articles associated with the same...

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Organozinc chemistry

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PMID 16900548. In this example the arylzinc iodide continues to react with allyl bromide in a nucleophilic displacement Merck Index. Merck & Co. 2001. ISBN 9780911910131...

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1933 in science

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radicals are responsible for anti-Markovnikov addition of hydrogen bromide to allyl bromide. March 10 – Long Beach earthquake in Southern California: First...

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