Propargyl bromide

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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
UNII
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., gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gasReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerinSpecial 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 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[edit]

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[edit]

Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[4]

Reactions[edit]

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]

Barbier reaction

Safety[edit]

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

See also[edit]

References[edit]

  1. ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  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.; Collective Volume, 7, p. 485
  4. ^ "Process for Producing Propargyl Bromide". Retrieved November 7, 2012.
  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.
  7. ^ "3-Bromo-1-Propyne". Retrieved November 3, 2012.