2-Bromopropane

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2-Bromopropane
Skeletal formula of 2-bromopropane
Skeletal formula of 2-bromopropane with all explicit hydrogens added
Ball and stick model of 2-bromopropane Spacefill model of 2-bromopropane
Identifiers
CAS number 75-26-3 YesY
PubChem 6358
ChemSpider 6118 YesY
EC number 200-855-1
UN number 2344
MeSH 2-bromopropane
ChEMBL CHEMBL451810 YesY
RTECS number TX4111000
Beilstein Reference 741852
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water 3.2 g L−1 (at 20 °C)
log P 2.136
Vapor pressure 32 kPa (at 20 °C)
kH 1.0 μmol Pa−1 mol−1
Refractive index (nD) 1.4251
Viscosity 4.894 mPa s (at 20 °C)
Thermochemistry
Specific
heat capacity
C
135.6 J K mol−1
Std enthalpy of
formation
ΔfHo298
−129 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−2.0537–−2.0501 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H225, H360, H373
GHS precautionary statements P210, P308+313
EU classification Highly Flammable F Toxic T
R-phrases R60, R11, R48/20, R66
S-phrases S16, S45
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
Flash point 19 °C (66 °F; 292 K)
Related compounds
Related alkanes
Except where noted otherwise, 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[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]

Reactions[edit]

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[edit]

Alkylating agents are often carcinogenic.

Further reading[edit]

  • M G. 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. ^ "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: 25 
  5. ^ C. R. Noller and R. Dinsmore (1943), "Isobutyl bromide", Org. Synth. ; Coll. Vol. 2: 358