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 ;
	show InChI
	show SMILES
Properties
Chemical formula	C3H3Br
Molar mass	118.961 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)
Solubility in water	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 (fire diamond)	3 3 4
Flash point	18 °C (64 °F; 291 K)
Autoignition; temperature	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.

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]

References[]

^ Jump up to: ^a ^b ^c ^d ^e ^f 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.CS1 maint: multiple names: authors list (link); Collective Volume, 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.

[GESTIS-1] Jump up to: ^a ^b ^c ^d ^e ^f 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.CS1 maint: multiple names: authors list (link); Collective Volume, 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.

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