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词条 2-Bromopropane
释义

  1. Preparation

  2. Reactions

  3. Safety

  4. Further reading

  5. References

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477195300
| ImageFile = 2-bromopropane-2D-skeletal.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| 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
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Ball and stick model of 2-bromopropane
| ImageFileR1 = 2-bromopropane-3D-vdW.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of 2-bromopropane
| IUPACName = 2-Bromopropane[1]
| OtherNames = Isopropyl bromide[2]
| Section1 = {{Chembox Identifiers
| CASNo = 75-26-3
| CASNo_Ref = {{cascite|correct|CAS}}
| 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}}
}}
| 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 = 4.894 mPa s (at 20 °C)
}}
| Section3 = {{Chembox Thermochemistry
| DeltaHf = −129 kJ mol−1
| DeltaHc = −2.0537–−2.0501 MJ mol−1
| HeatCapacity = 135.6 J K mol−1
}}
| 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
}}
| Section5 = {{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|Bromoethane|n-Propyl bromide|tert-Butyl bromide|1-Bromobutane|2-Bromobutane}}
}}
}}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

1. ^{{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}}
2. ^Wilfred L.F. Armarego and Christina Li Lin Chai, Purification of laboratory chemicals, 7th edition, Butterworth-Heinemann, 2013, [https://books.google.com/books?id=4ViVUQi7Z60C&pg=PA176 p. 176]
3. ^Merck Index of Chemicals and Drugs, 9th ed. Monograph 5071
4. ^{{OrgSynth | title = Alkyl and alkylene bromides | author = Oliver Kamm and C. S. Marvel | collvol = 1 | collvolpages = 25 | year = 1941}}
5. ^{{OrgSynth | author = C. R. Noller and R. Dinsmore | title = Isobutyl bromide | collvol = 2 | collvolpages = 358 | year = 1943}}
{{DEFAULTSORT:Bromopropane2}}

3 : Bromoalkanes|Alkylating agents|Isopropyl compounds

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