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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 |chapter=Monograph 6526 |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 |chchapte526 |url=https://www.rsc.org/Merck-Index/monograph/m6526/ }}</ref>


==Preparation== ==Preparation==

Revision as of 15:52, 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. Merck Index of Chemicals and Drugs. {{cite book}}: Text "chchapte526" ignored (help)
  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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