2-Bromopropane

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| ImageFile = 2-bromopropane-2D-skeletal.png

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| ImageName = Skeletal formula of 2-bromopropane

| ImageFile1 = 2-bromopropane-2D-flat.png

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| ImageSize1 = 160

| ImageName1 = Skeletal formula of 2-bromopropane with all explicit hydrogens added

| ImageFileL1 = 2-bromopropane-3D-balls.png

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| ImageNameL1 = Ball and stick model of 2-bromopropane

| ImageFileR1 = 2-bromopropane-3D-vdW.png

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| ImageNameR1 = Spacefill model of 2-bromopropane

| PIN = 2-Bromopropane{{Cite web|title=2-bromopropane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6358&loc=ec_rcs#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=15 June 2012|location=USA|date=27 March 2005|at=Identification}}

| OtherNames = Isopropyl bromide{{cite book |first1=Wilfred L.F. |last1=Armarego |first2=Christina |last2=Li Lin Chai |title=Purification of laboratory chemicals |edition=7th |publisher=Butterworth-Heinemann |year=2013 |url=https://books.google.com/books?id=4ViVUQi7Z60C&pg=PA176 |page=176 |isbn=9780123821621 }}

| Section1 = {{Chembox Identifiers

| CASNo = 75-26-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R651XOV97Z

| PubChem = 6358

| ChemSpiderID = 6118

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 200-855-1

| UNNumber = 2344

| MeSHName = 2-bromopropane

| ChEMBL = 451810

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = TX4111000

| Beilstein = 741852

| SMILES = CC(C)Br

| StdInChI = 1S/C3H7Br/c1-3(2)4/h3H,1-2H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NAMYKGVDVNBCFQ-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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| Section2 = {{Chembox Properties

| C = 3

| H = 7

| Br = 1

| Appearance = Colorless liquid

| Density = 1.31 g mL−1

| MeltingPtK = 184.2

| BoilingPtK = 332 to 334

| Solubility = 3.2 g L−1 (at 20 °C)

| LogP = 2.136

| VaporPressure = 32 kPa (at 20 °C)

| HenryConstant = 1.0 μmol Pa−1 mol−1

| RefractIndex = 1.4251

| Viscosity = 0.4894 mPa s (at 20 °C)

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| Section3 = {{Chembox Thermochemistry

| DeltaHf = −129 kJ mol−1

| DeltaHc = −2.0537–−2.0501 MJ mol−1

| HeatCapacity = 135.6 J K mol−1

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| Section4 = {{Chembox Hazards

| GHSPictograms = {{GHS flame}} {{GHS health hazard}}

| GHSSignalWord = DANGER

| HPhrases = {{H-phrases|225|360|373}}

| PPhrases = {{P-phrases|210|308+313}}

| NFPA-H = 2

| NFPA-F = 3

| NFPA-R = 0

| FlashPtC = 19

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| Section5 = {{Chembox Related

| OtherFunction_label = alkanes

| OtherFunction = {{Unbulleted list|Bromoethane|1-Bromopropane|tert-Butyl bromide|1-Bromobutane|2-Bromobutane}}

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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.{{cite book |title=Merck Index of Chemicals and Drugs |chapter=Monograph 6526 |url=https://www.rsc.org/Merck-Index/monograph/m6526/ }}

Preparation

2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine,{{OrgSynth | title = Alkyl and alkylene bromides | author = Oliver Kamm and C. S. Marvel | collvol = 1 | collvolpages = 25 | year = 1941}} or with phosphorus tribromide.{{OrgSynth | author = C. R. Noller and R. Dinsmore | title = Isobutyl bromide | collvol = 2 | collvolpages = 358 | year = 1943}}

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