Dibromomethane or methylene bromide, or methylene dibromide is a halomethane with the formula CH2Br2. It is slightly soluble in water but very soluble in organic solvents. It is a colorless liquid.
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| Names | |
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| Preferred IUPAC name
Dibromomethane[1] | |
Other names
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| Identifiers | |
3D model (JSmol)
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| Abbreviations |
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| 969143 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.750 |
| EC Number |
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| 25649 | |
| MeSH | methylene+bromide |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2664 |
CompTox Dashboard (EPA)
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| Properties | |
| CH2Br2 | |
| Molar mass | 173.835 g·mol−1 |
| Appearance | Colorless to yellow liquid |
| Density | 2.477 g⋅mL−1 |
| Melting point | −52.70 °C; −62.86 °F; 220.45 K |
| Boiling point | 96 to 98 °C; 205 to 208 °F; 369 to 371 K |
| 12.5 g⋅L−1 (at 20 °C) | |
| Vapor pressure | 4.65 kPa (at 20.0 °C) |
Henry's law
constant (kH) |
9.3 μmol⋅Pa−1⋅kg−1 |
| −65.10·10−6⋅cm3/mol | |
Refractive index (nD)
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1.541 |
| Thermochemistry | |
Heat capacity (C)
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104.1 J⋅K−1⋅mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H332, H412 | |
| P273 | |
| NFPA 704 (fire diamond) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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| 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).
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Physical properties
editAt ambient temperature, dibromomethane freezes around 0.61 GPa. The crystal structure strongly suggests both interhalogen and hydrogen-halogen interactions.[2]
Preparation
editDibromomethane is prepared commercially from dichloromethane via bromochloromethane:
- 6 CH2Cl2 + 3 Br2 + 2 Al → 6 CH2BrCl + 2 AlCl3
- CH2Cl2 + HBr → CH2BrCl + HCl
The latter route requires aluminium trichloride as a catalyst.[3] The bromochloromethane product from either reaction can further react in a similar manner:
- 6 CH2BrCl + 3 Br2 + 2 Al → 6 CH2Br2 + 2 AlCl3
- CH2BrCl + HBr → CH2Br2 + HCl
In the laboratory, it is prepared from bromoform using sodium arsenite and sodium hydroxide:[4]
- CHBr3 + Na3AsO3 + NaOH → CH2Br2 + Na3AsO4 + NaBr
Another way is to prepare it from diiodomethane and bromine.
Uses
editDibromomethane is used as a solvent, gauge fluid, and in organic synthesis (often as 1H-NMR internal standard).[3] It conviently converts polyols (such as catechols) to their methylenedioxy derivatives, and bromomethylenates enolates. It is a much cheaper precursor to a Simmons-Smith-type reagent than diiodomethane.[5]
Natural occurrence
editIt is naturally produced by marine algae and liberated to the oceans. Releasing on soil causes it to evaporate and leach into the ground. Releasing in water causes it to be lost mainly by volatilisation with a half life of 5.2 hours. It has no significant degradation biological or abiological effects. In the atmosphere it will be lost because of reaction with photochemically produced hydroxyl radicals. The estimated half life of this reaction is 213 days.
References
edit- ^ "methylene bromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 18 June 2012.
- ^ Podsiadlo M.; Dziubek K.; Szafranski M.; Katrusiak A. (December 2006). "Molecular interactions in crystalline dibromomethane and diiodomethane, and the stabilities of their high-pressure and low-temperature phases" (PDF). Acta Crystallogr. B. 62 (6): 1090–1098(9). doi:10.1107/S0108768106034963. PMID 17108664. Retrieved 2007-06-29.
- ^ a b Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN 978-3527306732.
- ^ W. W. Hartman, E. E. Dreger (1929). "Methylene bromide". Org. Synth. 9: 56. doi:10.15227/orgsyn.009.0056.
- ^ Matteson, Donald S. "Dibromomethane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd044.