Propargyl bromide

Propargyl bromide
Names
IUPAC name
3-Bromo-1-propyne
Other names
Bromopropyne, 1-Brom-2-propin, 1-Bromo-2-propyne Gamma-bromoallylene, 1-Bromo-2-propyne, 2-Propynyl bromide, Propargyl bromide, Propynyl bromide, gamma-Bromoallylene
Identifiers
106-96-7
ChemSpider 7554
Jmol interactive 3D Image
PubChem 7842
Properties
C3H3Br
Molar mass 118.96 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
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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazards (white): no codeNFPA 704 four-colored diamond
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

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 an alkyl functional group with 2-propynyl group linked to bromide. It has a lachrymatory effect, like related compounds. The compound is a useful reagent in organic synthesis.


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]

See also

References

  1. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the IFA
  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". Org. Synth. 60: 41.; Coll. Vol. 7, p. 485
  4. "Process for Producing Propargyl Bromide". Retrieved November 7, 2012.
  5. "Propargyl Bromide". Retrieved November 5, 2012.
  6. Artur Jõgi and 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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