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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.135 Edit this at Wikidata
UNII
  • InChI=1S/C3H3Br/c1-2-3-4/h1H,3H2
  • BrCC#C
Properties
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]
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
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).

Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, 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 used as a reagent in organic synthesis.

Applications and production

Propargyl bromide can also be used as an intermediate for the synthesis of organic compounds, including agrochemicals and pharmaceuticals. In the 1960s, it was used in a soil fumigant called Trizone.[2]

Propargyl bromide may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[3]

Reactions

Propargyl bromide is an alkylating agent. With dimethylsulfide, it reacts to give the sulfonium salt:[4]

HCCCH2Br + S(CH3)2 → [HCCCH2S(CH3)2]Br

It also alkylates even weakly basic amines such as aniline.[5]

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

Barbier reaction

At low temperatures, upon treatment with magnesium, propargyl bromide gives the Grignard reagent formally derived from allenyl bromide, i.e., CH2=C=CHMgBr.[7]

Safety

Propargyl bromide is a lachrymator and an alkylating agent.[8]

See also

References

  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. ^ "Process for Producing Propargyl Bromide". Retrieved November 7, 2012.
  4. ^ P. D. Howes, C. J. M. Stirling (1973). "3-Acetyl-2,4-Dimethylfuran". Organic Syntheses. 53: 1. doi:10.15227/orgsyn.053.0001.
  5. ^ Yu Chen, Anton Dubrovskiy, Richard C. Larock (2012). "Synthesis of Quinolines by Electrophilic Cyclization of N-(2-Alkynyl)Anilines: 3-Iodo-4-Phenylquinoline". Organic Syntheses. 89: 294. doi:10.15227/orgsyn.089.0294.((cite journal)): CS1 maint: multiple names: authors list (link)
  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. ^ 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
  8. ^ "3-Bromo-1-Propyne". Retrieved November 3, 2012.
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