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2-Bromopropane
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changed changed 477195300 2-bromopropane-2D-skeletal.png correct ?? 100 Skeletal formula of 2-bromopropane skin-invert 2-bromopropane-2D-flat.png correct ?? 160 Skeletal formula of 2-bromopropane with all explicit hydrogens added skin-invert 2-bromopropane-3D-balls.png correct ?? Ball and stick model of 2-bromopropane bg-transparent 2-bromopropane-3D-vdW.png correct ?? Spacefill model of 2-bromopropane bg-transparent 2-Bromopropane2-bromopropane - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/6358 PubChem Compound National Center for Biotechnology Information 15 June 2012 USA 27 March 2005 Identification Isopropyl bromideWilfred L.F. Armarego Christina Li Lin Chai Purification of laboratory chemicals 7th Butterworth-Heinemann 2013 https://books.google.com/books?id=4ViVUQi7Z60C&pg=PA176 176 9780123821621 75-26-3 correct CAS i-PrBriPrBriPrBr correct FDA R651XOV97Z 6358 6118 correct chemspider 200-855-1 2344 2-bromopropane 451810 correct EBI TX4111000 741852 CC(C)Br 1S/C3H7Br/c1-3(2)4/h3H,1-2H3 correct chemspider NAMYKGVDVNBCFQ-UHFFFAOYSA-N correct chemspider 3 7 1 Colorless liquid 1.31 g mL−1 184.2 332 to 334 3.2 g L−1 (at 20 °C) 2.136 32 kPa (at 20 °C) 1.0 μmol Pa−1 mol−1 1.4251 0.4894 mPa s (at 20 °C) −129 kJ mol−1 −2.0537–−2.0501 MJ mol−1 135.6 J K mol−1 flame health hazard DANGER 225 360 373 210 308+313 2 3 0 19 alkanes Bromoethane 1-Bromopropane tert-Butyl bromide 1-Bromobutane 2-Bromobutane
2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula C3H7Br 1 or CH3CHBrCH3. It is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.Merck Index of Chemicals and Drugs Monograph 6526 https://www.rsc.org/Merck-Index/monograph/m6526/
Preparation
2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine, Alkyl and alkylene bromides Oliver Kamm and C. S. Marvel 1 25 1941 or with phosphorus tribromide. C. R. Noller and R. Dinsmore Isobutyl bromide 2 358 1943
The organomercury compound diisopropylmercury may be prepared through the magnesium-catalysed reaction of 2-bromopropane with mercuric chloride.https://pubs.acs.org/doi/book/10.1021/ba-1972-0112 Ozone Reactions with Organic Compounds 1972-06-01 AMERICAN CHEMICAL SOCIETY 978-0-8412-0152-1 Bailey Philip S. The Ozonolysis of Organomercurials Advances in Chemistry 112 78–100 WASHINGTON, D. C. en 10.1021/ba-1972-0112.ch007
Safety
Short-chain alkyl halides are often carcinogenic.
The bromine atom is at the secondary position, which allows the molecule to undergo dehydrohalogenation easily to give propene, which escapes as a gas and can rupture closed reaction vessels. When this reagent is used in base catalyzed reactions, potassium carbonate should be used in place of sodium or potassium hydroxide.
Further reading
Max Gergel, “Excuse Me Sir, Would You Like to Buy a Kilo of Isopropyl Bromide?” Pierce Chemical Co. (1979). (story of start-up chemical company).
References
Category:Bromoalkanes
Category:Alkylating agents
Category:Isopropyl compounds
Category:IARC Group 2A carcinogens