2-Bromopropane
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| verifiedrevid = 477195300
| ImageFile = 2-bromopropane-2D-skeletal.png
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| ImageSize = 100
| ImageName = Skeletal formula of 2-bromopropane
| ImageFile1 = 2-bromopropane-2D-flat.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| 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
| 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
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