2-Bromopropane

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]

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
Preferred IUPAC name 2-Bromopropane[1]
Other names Isopropyl bromide[2]
Identifiers
CAS Number	75-26-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	741852
ChEMBL	ChEMBL451810 Y
ChemSpider	6118 Y
ECHA InfoCard	100.000.778
EC Number	200-855-1
MeSH	2-bromopropane
PubChem CID	6358
RTECS number	TX4111000
UNII	R651XOV97Z Y
UN number	2344
CompTox Dashboard (EPA)	DTXSID7030197
InChI InChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3 Y Key: NAMYKGVDVNBCFQ-UHFFFAOYSA-N Y
SMILES CC(C)Br
Properties
Chemical formula	C3H7Br
Molar mass	122.993 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)
Henry's law constant (kH)	1.0 μmol Pa−1 mol−1
Refractive index (nD)	1.4251
Viscosity	0.4894 mPa s (at 20 °C)
Thermochemistry
Heat capacity (C)	135.6 J K mol−1
Std enthalpy of formation (ΔfH⦵298)	−129 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−2.0537–−2.0501 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H360, H373
Precautionary statements	P210, P308+P313
NFPA 704 (fire diamond)	2 3 0
Flash point	19 °C (66 °F; 292 K)
Related compounds
Related alkanes	Bromoethane 1-Bromopropane tert-Butyl bromide 1-Bromobutane 2-Bromobutane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]

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. "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
2. Armarego, Wilfred L.F.; Li Lin Chai, Christina (2013). Purification of laboratory chemicals (7th ed.). Butterworth-Heinemann. p. 176. ISBN 9780123821621.
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.