2-Bromopropane

2-Bromopropane
Names
IUPAC name
2-Bromopropane[1]
Other names
Isopropyl bromide[2]
Identifiers
3D model (JSmol)
741852
ChemSpider
ECHA InfoCard 100.000.778
EC Number 200-855-1
MeSH 2-bromopropane
RTECS number TX4111000
UN number 2344
Properties
C3H7Br
Molar mass 122.99 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 4.894 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 pictograms
GHS signal word DANGER
H225, H360, H373
P210, P308+313
NFPA 704
Flammability code 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., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
2
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).
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Infobox references

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]

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]

Reactions

The bromine atom is at the secondary position, which allows the molecule to undergo dehydrohalogenation easily to give propene, which escapes as a gas. Consequently, this reagent is used in conjunction with mild bases, such as potassium carbonate, rather than strong ones.

Safety

Alkylating agents are often carcinogenic.

Further reading

References

  1. ↑ "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  2. ↑ Wilfred L.F. Armarego and Christina Li Lin Chai, Purification of laboratory chemicals, 7th edition, Butterworth-Heinemann, 2013, p. 176
  3. ↑ Merck Index of Chemicals and Drugs, 9th ed. Monograph 5071
  4. ↑ Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides". Org. Synth.; Coll. Vol., 1, p. 25
  5. ↑ C. R. Noller and R. Dinsmore (1943). "Isobutyl bromide". Org. Synth.; Coll. Vol., 2, p. 358
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