*** Welcome to piglix ***

Propargyl bromide

Propargyl bromide
Propargyl bromide.svg
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
1-Bromo-2-propyne
2-Propynyl bromide
Propargyl bromide
Propynyl bromide
gamma-Bromoallylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.135
PubChem CID
UNII
Properties
C3H3Br
Molar mass 118.96 g·mol−1
Appearance colourless liquid
Density 1.57 g/mL (20 °C)
Melting point −61.1 °C (−78.0 °F; 212.1 K)
Boiling point 89 °C (192 °F; 362 K)
Insoluble
Solubility Soluble in organic solvents
log P 1.179
Vapor pressure 72 mbar (20 °C)
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
Flash point 18 °C (64 °F; 291 K)
324 °C (615 °F; 597 K)
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 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.

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

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.

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

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

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

Propargyl bromide is a lachrymator and an alkylating agent.


...
Wikipedia

...