2-Bromopropane

2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula 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.[3]

2-Bromopropane
Skeletal formula of 2-bromopropane
Skeletal formula of 2-bromopropane with all explicit hydrogens added
Ball and stick model of 2-bromopropane
Ball and stick model of 2-bromopropane
Spacefill model of 2-bromopropane
Spacefill model of 2-bromopropane
Names
Preferred IUPAC name
2-Bromopropane[1]
Other names
Isopropyl bromide[2]
Identifiers
3D model (JSmol)
741852
ChEMBL
ChemSpider
ECHA InfoCard 100.000.778
EC Number
  • 200-855-1
MeSH 2-bromopropane
RTECS number
  • TX4111000
UNII
UN number 2344
  • InChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3 checkY
    Key: NAMYKGVDVNBCFQ-UHFFFAOYSA-N checkY
  • CC(C)Br
Properties
C3H7Br
Molar mass 122.993 g·mol−1
Appearance Colorless liquid
Density 1.31 g mL−1
Melting point −89.0 °C; −128.1 °F; 184.2 K
Boiling point 59 to 61 °C; 138 to 142 °F; 332 to 334 K
3.2 g L−1 (at 20 °C)
log P 2.136
Vapor pressure 32 kPa (at 20 °C)
1.0 μmol Pa−1 mol−1
1.4251
Viscosity 0.4894 mPa s (at 20 °C)
Thermochemistry
135.6 J K mol−1
−129 kJ mol−1
−2.0537–−2.0501 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS08: Health hazard
Danger
H225, H360, H373
P210, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
3
0
Flash point 19 °C (66 °F; 292 K)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Preparation

2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine,[4] or with phosphorus tribromide.[5]

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
  1. "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  2. Armarego, Wilfred L.F.; Li Lin Chai, Christina (2013). Purification of laboratory chemicals (7th ed.). Butterworth-Heinemann. p. 176. ISBN 9780123821621.
  3. "Monograph 6526". Merck Index of Chemicals and Drugs.
  4. Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides". Organic Syntheses.; Collective Volume, vol. 1, p. 25
  5. C. R. Noller and R. Dinsmore (1943). "Isobutyl bromide". Organic Syntheses.; Collective Volume, vol. 2, p. 358
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