2-Bromopropane

2-Bromopropane
IUPAC name 2-Bromopropane[1]
Other names Isopropyl bromide[2]
Identifiers
CAS number	75-26-3 Y
PubChem	6358
ChemSpider	6118 Y
EC number	200-855-1
UN number	2344
MeSH	2-bromopropane
ChEMBL	CHEMBL451810 Y
RTECS number	TX4111000
Beilstein Reference	741852
Jmol-3D images	Image 1
SMILES CC(C)Br
InChI InChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3 Y Key: NAMYKGVDVNBCFQ-UHFFFAOYSA-N Y
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
Std enthalpy of formation ΔfHo298	−129 kJ mol−1
Std enthalpy of combustion ΔcHo298	−2.0537–−2.0501 MJ mol−1
Specific heat capacity, C	135.6 J K mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H360, H373
GHS precautionary statements	P210, P308+313
EU classification	F T
R-phrases	R60, R11, R48/20, R66
S-phrases	S16, S45
NFPA 704	3 2 0
Flash point	19 °C; 66 °F; 292 K
Related compounds
Related alkanes	Bromoethane n-Propyl bromide tert-Butyl bromide 1-Bromobutane 2-Bromobutane
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

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

Alkylating agents are often carcinogenic.

Further reading

• 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