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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| ChemSpider | |
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 may be produced by the treatment of propargyl alcohol with phosphorus tribromide.[2]
Reactions
Propargyl bromide is an alkylating agent. For example, it reacts with dimethylsulfide, it reacts to give the sulfonium salt:[3]
- HCCCH
2Br + S(CH
3)
2 → [HCCCH
2S(CH
3)
2]Br
It alkylates even weakly basic amines such as aniline.[4]
Aldehydes react with propargyl bromide in a Barbier-type reaction to yield alkynyl alcohols:[5]
- 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.[6]
Propargyl bromide and its ether derivatives participate in azide-based click reactions.[7]
Safety
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
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
- ↑ "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.
- ↑ Jõgi, Artur; Mäeorg, Uno (30 November 2001). "Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution". Molecules 6 (12): 964–968. doi:10.3390/61200964.
- ↑ 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. doi:10.15227/orgsyn.060.0041.
- ↑ Wu, Peng; Feldman, Alina K.; Nugent, Anne K.; Hawker, Craig J.; Scheel, Arnulf; Voit, Brigitte; Pyun, Jeffrey; Fréchet, Jean M. J. et al. (2004). "Efficiency and Fidelity in a Click-Chemistry Route to Triazole Dendrimers by the Copper(I)-Catalyzed Ligation of Azides and Alkynes". Angewandte Chemie International Edition 43 (30): 3928–3932. doi:10.1002/anie.200454078. PMID 15274216.
- ↑ "3-Bromo-1-Propyne". https://www.nlm.nih.gov/toxnet/index.html.
- ↑ 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.
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