Propargyl bromide

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
CAS Number	106-96-7;
3D model (JSmol)	Interactive image;
ChemSpider	7554;
ECHA InfoCard	100.003.135
PubChem CID	7842;
UNII	F3H7ZXK9ZU ;
CompTox Dashboard (EPA)	DTXSID3042340 ;
	InChI InChI=1S/C3H3Br/c1-2-3-4/h1H,3H2;
	SMILES BrCC#C;
Properties
Chemical formula	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]
Solubility in water	Insoluble
Solubility	Soluble in organic solvents
log P	1.179
Vapor pressure	72 mbar (20 °C)[1]
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly Flammable, Toxic, Corrosive
NFPA 704 (fire diamond)	3 3 4
Flash point	18 °C (64 °F; 291 K)[1]
Autoignition; temperature	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 HC≡CCH₂Br. 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.

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 propargylamines, propargylation of spiro ketones, production of allylic alcohols, and enone complexes.[5]

Aldehydes may be treacted with propargyl bromide in a Barbier-type reaction to yield alkynyl alcohols:[6]

Safety

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

References

Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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
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.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 7, p. 485
"Process for Producing Propargyl Bromide". Retrieved November 7, 2012.
"Propargyl Bromide". Retrieved November 5, 2012.
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.
"3-Bromo-1-Propyne". Retrieved November 3, 2012.

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[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[Ullmanns-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.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 7, p. 485

[FreePatentsOnline-4] "Process for Producing Propargyl Bromide". Retrieved November 7, 2012.

[Chemicalland21-5] "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.

[toxnet-7] "3-Bromo-1-Propyne". Retrieved November 3, 2012.