1,3-Dibromopropane is an organobromine compound with the formula (CH2)3Br2. It is a colorless liquid with sweet odor. It is used in organic synthesis to form C3-bridged compounds such as through C-N coupling reactions.
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| Names | |||
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| Preferred IUPAC name
1,3-Dibromopropane[3] | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol)
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| 635662 | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.356 | ||
| EC Number |
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| MeSH | 1,3-dibromopropane | ||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 1993 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C3H6Br2 | |||
| Molar mass | 201.889 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)
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1.524 | ||
| Thermochemistry | |||
Heat capacity (C)
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163.7 J K mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
  
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| Warning | |||
| H226, H302, H315, H411 | |||
| P273 | |||
| Flash point | 56 °C (133 °F; 329 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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315 mg kg−1 (oral, rat) | ||
| Related compounds | |||
Related alkanes
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Related compounds
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Mitobronitol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Dibromopropane was used in the first cyclopropane synthesis in 1881, known as the Freund reaction.[4]
Synthesis
edit1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[5]
Metabolism
editMetabolism of 1,3-dibromopropane was examined in 1981.[6] The examination was done by orally administering 1,3-dibromopropane to rats and collecting results 24 hours 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 feces and the confirmation from maintained blood levels of radioactivity proved the occurrence of biliary excretion of sulfur-containing metabolites and enterohepatic cycling.
References
edit- ^ Creese, Mary R. S. (2015). Ladies in the Laboratory IV: Imperial Russia's Women in Science, 1800-1900: A Survey of Their Contributions to Research. Rowman & Littlefield. p. 57. ISBN 978-1-4422-4742-0.
- ^ "1,3-Dibromopropane". pubchem.ncbi.nlm.nih.gov.
- ^ "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. PMID 7245244.