1,3-Dibromopropane
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| Names | |||
|---|---|---|---|
| IUPAC name
1,3-Dibromopropane[1] | |||
Other names
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| Identifiers | |||
| 3D model (JSmol) |
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| 635662 | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.356 | ||
| EC Number | 203-690-3 | ||
| MeSH | 1,3-dibromopropane | ||
| PubChem CID |
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| RTECS number | TX8575000 | ||
| UNII | |||
| UN number | 1993 | ||
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| Properties | |||
| C3H6Br2 | |||
| Molar mass | 201.89 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 1.989 g mL−1 | ||
| Melting point | −34.20 °C; −29.56 °F; 238.95 K | ||
| Boiling point | 167 °C; 332 °F; 440 K | ||
| Henry's law constant (kH) |
11 μmol Pa−1 kg−1 | ||
| Refractive index (nD) |
1.524 | ||
| Thermochemistry | |||
| 163.7 J K mol−1 | |||
| Hazards | |||
| GHS pictograms |    | ||
| GHS signal word | WARNING | ||
| H226, H302, H315, H411 | |||
| P273 | |||
| Flash point | 56 °C (133 °F; 329 K) | ||
| Lethal dose or concentration (LD, LC): | |||
| LD50 (median dose) |
315 mg kg−1 (oral, rat) | ||
| Related compounds | |||
| Related alkanes |
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| Related compounds |
Mitobronitol | ||
| 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 | |||
1,3-Dibromopropane is a halogenated hydrocarbon. When at room temperature, it is a colorless to light-brown liquid containing sweet odor. Synthetically, it is very useful to form C3-bridged compounds such as through C-N coupling reactions.
1,3-Dibromopropane was used in the first cyclopropane synthesis in 1881, known as the Freund reaction.[2]
Synthesis
1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[3]
Metabolism
Metabolism of 1,3-Dibromopropane was examined in 1981.[4] The examination was done by orally administering 1,3-dibromopropane to rats and collection results 24hours after administration. Results were obtained from three sources: urine, faeces, and expired air. Upon analysis of the urinary results, researchers discovered the formation of metabolite, N-acetyl-S-( 1-bromo-3-propyl)-cysteine and the decline in the GSH content of the liver of the rats. This led to the assumption that 1,3-dibromopropane could have reacted with GSH after administration and gave rise to 1-bromo-3-propyl-S-glutathione, which ultimately form the urinary metabolite. Moreover, due to little radioactivity observed from faeces and the confirmation from maintained blood levels of radioactivity proved the occurrence of biliary excretion of sulphur-containing metabolites and enterohepatic cycling.
References
- ↑ "1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012.
- ↑ August Freund (1882). "Ueber Trimethylen". Journal für Praktische Chemie. 26 (1): 367–377. doi:10.1002/prac.18820260125.
- ↑ W. E. Vaughan; F. F. Rust; T. W. Evans (1942). "The photo-addition of hydrogen bromide to olefinic bonds". Journal of Organic Chemistry. 7 (6): 477–490. doi:10.1021/jo01200a005.
- ↑ S. P. James; M. A. Put; D. H. Richards (1981). "Metabolism of 1,3-dibromopropane". Toxicology letters. 8 (1-2): 7–15. doi:10.1016/0378-4274(81)90130-2.