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Propargyl bromide

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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

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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

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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

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Propargyl bromide is a lachrymator and an alkylating agent.[8] This liquid acetylenic endothermic compound may be decomposed by mild shock, and when heated under confinement, it decomposes with explosive violence and may detonate. Addition of 20—30 wt% of toluene makes propargyl bromide insensitive in laboratory impact and confinement tests.[9]

See also

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References

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  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. ^ Jõgi, Artur; Mäeorg, Uno (30 November 2001). "Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH
    4
    Cl
    Solution"
    . Molecules. 6 (12): 964–968. doi:10.3390/61200964.
  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); Collected Volumes, vol. 7, p. 485.
  8. ^ "3-Bromo-1-Propyne". Retrieved November 3, 2012.
  9. ^ Urben, P.G., ed. (2017). "C1". Bretherick's Handbook of Reactive Chemical Hazards. pp. 81–882. doi:10.1016/B978-0-08-100971-0.00055-X. ISBN 978-0-08-100971-0.