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'''2-Bromopropane''', also known as '''isopropyl bromide''' and '''2-propyl bromide''', is the ]ated ] with the formula CH<sub>3</sub>CHBrCH<sub>3</sub>. It is a colorless liquid. It is used for introducing the isopropyl ] in ]. 2-Bromopropane is prepared by heating ] with ].<ref>{{cite book |title=Merck Index of Chemicals and Drugs |chchapte526 |url=https://www.rsc.org/Merck-Index/monograph/m6526/ }}</ref> '''2-Bromopropane''', also known as '''isopropyl bromide''' and '''2-propyl bromide''', is the ]ated ] with the formula CH<sub>3</sub>CHBrCH<sub>3</sub>. It is a colorless liquid. It is used for introducing the isopropyl ] in ]. 2-Bromopropane is prepared by heating ] with ].<ref>{{cite book |title=Merck Index of Chemicals and Drugs |chapter=Monograph 6526 |url=https://www.rsc.org/Merck-Index/monograph/m6526/ }}</ref>


==Preparation== ==Preparation==

Revision as of 15:54, 8 December 2023

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
Other names Isopropyl bromide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 741852
ChEMBL
ChemSpider
ECHA InfoCard 100.000.778 Edit this at Wikidata
EC Number
  • 200-855-1
MeSH 2-bromopropane
PubChem CID
RTECS number
  • TX4111000
UNII
UN number 2344
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3Key: NAMYKGVDVNBCFQ-UHFFFAOYSA-N
SMILES
  • CC(C)Br
Properties
Chemical formula C3H7Br
Molar mass 122.993 g·mol
Appearance Colorless liquid
Density 1.31 g mL
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 (at 20 °C)
log P 2.136
Vapor pressure 32 kPa (at 20 °C)
Henry's law
constant (kH) 		1.0 μmol Pa mol
Refractive index (nD) 1.4251
Viscosity 0.4894 mPa s (at 20 °C)
Thermochemistry
Heat capacity (C) 135.6 J K mol
Std enthalpy of
formation (ΔfH298) 		−129 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−2.0537–−2.0501 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS08: Health hazard
Signal word Danger
Hazard statements H225, H360, H373
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

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. 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.
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