1,3-Dibromopropane
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| Names | |||
|---|---|---|---|
| IUPAC name
1,3-Dibromopropane[1] | |||
Other names
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| Identifiers | |||
109-64-8  | |||
| 3D model (Jmol) | Interactive image | ||
| 635662 | |||
| ChemSpider | 7710 | ||
| ECHA InfoCard | 100.003.356 | ||
| EC Number | 203-690-3 | ||
| MeSH | 1,3-dibromopropane | ||
| PubChem | 8001 | ||
| RTECS number | TX8575000 | ||
| UNII | YQR3048IX9 | ||
| 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 | |||
| EU classification (DSD) |
 Xn  N | ||
| R-phrases | R10, R22, R38, R51/53 | ||
| S-phrases | S16, S26, S36 | ||
| 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. 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]
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.
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