Wikipedia

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[2]
Other names
Isopropyl bromide[1]
Identifiers
3D model (JSmol)
741852
ChEMBL
ChemSpider
ECHA InfoCard 100.000.778 Edit this at Wikidata
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 diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 ?)

Preparation

edit

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

edit

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

edit
  • 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

edit
  1. ^ Armarego, Wilfred L.F.; Li Lin Chai, Christina (2013). Purification of laboratory chemicals (7th ed.). Butterworth-Heinemann. p. 176. ISBN 9780123821621.
  2. ^ "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  3. ^ "Monograph 6526". Merck Index of Chemicals and Drugs.
  4. ^ Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides". Organic Syntheses; Collected Volumes, vol. 1, p. 25.
  5. ^ C. R. Noller and R. Dinsmore (1943). "Isobutyl bromide". Organic Syntheses; Collected Volumes, vol. 2, p. 358.
Retrieved from "https://en.wikipedia.org/w/index.php?title=2-Bromopropane&oldid=1192797556"