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-3D images Image
PubChem 7842
Properties
Molecular formula
 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 noted otherwise, data is 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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 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.