2-Bromopropane
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| Names | |||
|---|---|---|---|
| IUPAC name
2-Bromopropane[1] | |||
| Other names
Isopropyl bromide[2] | |||
| Identifiers | |||
75-26-3  | |||
| 3D model (Jmol) | Interactive image | ||
| 741852 | |||
| ChEMBL | ChEMBL451810 | ||
| ChemSpider | 6118 | ||
| ECHA InfoCard | 100.000.778 | ||
| EC Number | 200-855-1 | ||
| MeSH | 2-bromopropane | ||
| PubChem | 6358 | ||
| RTECS number | TX4111000 | ||
| UN number | 2344 | ||
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| Properties | |||
| 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 | ||
| 3.2 g L−1 (at 20 °C) | |||
| log P | 2.136 | ||
| Vapor pressure | 32 kPa (at 20 °C) | ||
| Henry's law constant (kH) |
1.0 μmol Pa−1 mol−1 | ||
| Refractive index (nD) |
1.4251 | ||
| Viscosity | 4.894 mPa s (at 20 °C) | ||
| Thermochemistry | |||
| 135.6 J K mol−1 | |||
| Std enthalpy of formation (ΔfH |
−129 kJ mol−1 | ||
| Std enthalpy of combustion (ΔcH |
−2.0537–−2.0501 MJ mol−1 | ||
| Hazards | |||
| GHS pictograms |   | ||
| GHS signal word | DANGER | ||
| H225, H360, H373 | |||
| P210, P308+313 | |||
| EU classification (DSD) |
 F  T | ||
| R-phrases | R60, R11, R48/20, R66 | ||
| S-phrases | S16, S45 | ||
| NFPA 704 | |||
| Flash point | 19 °C (66 °F; 292 K) | ||
| Related compounds | |||
| Related alkanes |
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| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is ?) | |||
| 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
- ↑ "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
- ↑ Wilfred L.F. Armarego and Christina Li Lin Chai, Purification of laboratory chemicals, 7th edition, Butterworth-Heinemann, 2013, p. 176
- ↑ Merck Index of Chemicals and Drugs, 9th ed. Monograph 5071
- ↑ Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides". Org. Synth.; Coll. Vol., 1, p. 25
- ↑ C. R. Noller and R. Dinsmore (1943). "Isobutyl bromide". Org. Synth.; Coll. Vol., 2, p. 358