Propargyl bromide

Propargyl bromide, also known as 3-bromo-1-propyne, is an organic compound with the chemical formula CHCCH2Br. It is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is a useful reagent in organic synthesis.

Propargyl bromide
Names
Preferred IUPAC name
3-Bromoprop-1-yne
Other names
3-Bromo-1-propyne
Bromopropyne
1-Brom-2-propin
1-Bromo-2-propyne
gamma-Bromoallylene
2-Propynyl bromide
Propargyl bromide
Propynyl bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.135
UNII
Properties
C3H3Br
Molar mass 118.961 g·mol−1
Appearance colourless liquid
Density 1.57 g/mL (20 °C)[1]
Melting point −61.1 °C (−78.0 °F; 212.1 K)[1]
Boiling point 89 °C (192 °F; 362 K)[1]
Insoluble
Solubility Soluble in organic solvents
log P 1.179
Vapor pressure 72 mbar (20 °C)[1]
Hazards
Main hazards Highly Flammable, Toxic, Corrosive
NFPA 704 (fire diamond)
Flammability code 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. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
3
3
4
Flash point 18 °C (64 °F; 291 K)[1]
324 °C (615 °F; 597 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Applications

In the 1960s, propargyl bromide was first used in a soil fumigant called Trizone.[2]

Propargyl bromide can also be used as an intermediate for the synthesis of organic compounds, including agrochemicals and pharmaceuticals. It forms a Grignard reagent at low temperatures, for example.[3]

Production

Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[4]

Reactions

Propargyl bromide can be used in enyne metathesis of propargylic amines, propargylation of spiro ketones, production of allylic alcohols, and enone complexes.[5]

Aldehydes may be reacted with propargyl bromide in a Barbier-type reaction to yield alkyne alcohols as well:[6]

Safety

Propargyl bromide is a lachrymator and an alkylating agent.[7]

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See also

References
  1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry, 2010, doi:10.1002/14356007.o28_o01
  3. Henning Hopf, Ingrid Böhm, and Jürgen Kleinschroth (1990). "Diels-Alder Reaction of 1,2,4,5-Hexatetraene: Tetramethyl[2.2]paracyclophane-4,5,12,13-tetracarboxylate". Organic Syntheses. 60: 41.CS1 maint: multiple names: authors list (link); Collective Volume, 7, p. 485
  4. "Process for Producing Propargyl Bromide". Retrieved November 7, 2012.
  5. "Propargyl Bromide". Retrieved November 5, 2012.
  6. Artur Jõgi & Uno Mäeorg (2001). "Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution" (PDF). Molecules. 6 (12): 964–968. doi:10.3390/61200964. ISSN 1420-3049.
  7. "3-Bromo-1-Propyne". Retrieved November 3, 2012.
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