2-Bromopropane

Chembox new
Name = 2-bromopropane
ImageFile = 2-bromopropane.svg
ImageSize = 90px
ImageName = 2-bromopropane
ImageFileL1 = 2-bromopropane-3D-balls.png ImageSizeL1 = 100px
ImageNameL1 = Ball-and-stick model of 2-bromopropane
ImageFileR1 = 2-bromopropane-3D-vdW.png ImageSizeR1 = 100px
ImageNameR1 = Space-filling model of 2-bromopropane
IUPACName = 2-bromopropane
OtherNames = isopropyl bromide
Section1 = Chembox Identifiers
SMILES = BrC(C)C
CASNo = 75-26-3
RTECS = TX4111000
Section2 = Chembox Properties
C=3|H=7|Br=1
Appearance = Pale brown to colorless liquid
Density = 1.31 g/mL, liquid
Solubility = 0.32 g/100 mL (20 °C)
Solubility1 = miscible
Solvent1 = organic solvents
RefractIndex = 1.4251
MeltingPtC = -90.0
BoilingPtC = 59.4
MeltingPt = -89°C (184 K)
BoilingPt = 59°C (332 K)
Viscosity = 6.106 cP at 0 °C 4.894 cP at 20 °C
Section3 = Chembox Structure
Dipole =
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/BR/2-bromopropane.html External MSDS]
MainHazards = Harmful, irritant
FlashPt = 22 °C
NFPA-H = 2
NFPA-F = 3
NFPA-R = 0
NFPA-O =
RPhrases = R10 R20 R36 R37 R38
SPhrases =
Section8 = Chembox Related
Function = alkyl halides
OtherFunctn = Ethyl bromide
n-propyl bromide
isopropyl chloride

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. [Merck Index of Chemicals and Drugs, 9th ed. Monograph 5071]

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, vs strong ones.

afety

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