Chemistry:Propargyl bromide
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| Names | |
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| 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)
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PubChem CID
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| 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 | |
| Main hazards | Highly Flammable, Toxic, Corrosive |
| NFPA 704 (fire diamond) | |
| 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-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]
- HCCCH
2Br + S(CH
3)
2 → [HCCCH
2S(CH
3)
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]
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
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 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
- ↑ "Process for Producing Propargyl Bromide". http://www.freepatentsonline.com/6794551.html. Retrieved November 7, 2012.
- ↑ P. D. Howes, C. J. M. Stirling (1973). "3-Acetyl-2,4-Dimethylfuran". Organic Syntheses 53: 1. doi:10.15227/orgsyn.053.0001.
- ↑ 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.
- ↑ Artur Jõgi; Uno Mäeorg (2001). "Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution". Molecules 6 (12): 964–968. doi:10.3390/61200964. ISSN 1420-3049. http://www.mdpi.org/molecules/papers/61200964.pdf.
- ↑ 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. http://www.orgsyn.org/demo.aspx?prep=CV7P0485.; Collective Volume, 7, pp. 485
- ↑ "3-Bromo-1-Propyne". http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+106-96-7. Retrieved November 3, 2012.
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