2-Bromopropane

From Wikipedia, the free encyclopedia
  (Redirected from 2-bromopropane)
Jump to: navigation, search
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
Names
IUPAC name
2-Bromopropane[2]
Other names
Isopropyl bromide[1]
Identifiers
741852
CAS number 75-26-3 YesY
ChEMBL ChEMBL451810 YesY
ChemSpider 6118 YesY
EC number 200-855-1
Jmol-3D images Image
MeSH 2-bromopropane
PubChem 6358
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 °C; 138 °F; 332 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 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
H225, H360, H373
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 is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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. ^ Wilfred L.F. Armarego and Christina Li Lin Chai, Purification of laboratory chemicals, 7th edition, Butterworth-Heinemann, 2013, p. 176
  2. ^ "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012. 
  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