1,3-Dibromopropane

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.

1,3-Dibromopropane
Ball and stick model of 1,3-dibromopropane
Spacefill model of 1,3-dibromopropane
Names
IUPAC name
1,3-Dibromopropane[1]
Other names
  • Trimethylenebromide[2]
  • Trimethylene dibromide[3]
Identifiers
3D model (JSmol)
635662
ChemSpider
ECHA InfoCard 100.003.356
EC Number
  • 203-690-3
MeSH 1,3-dibromopropane
RTECS number
  • TX8575000
UNII
UN number 1993
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
11 μmol Pa−1 kg−1
1.524
Thermochemistry
163.7 J K mol−1
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H226, H302, H315, H411
P273
Flash point 56 °C (133 °F; 329 K)
Lethal dose or concentration (LD, LC):
315 mg kg−1 (oral, rat)
Related compounds
Related alkanes
Related compounds
 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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Infobox references

1,3-Dibromopropane was used in the first cyclopropane synthesis in 1881, known as the Freund reaction.[4]

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.[5]

Metabolism

Metabolism of 1,3-dibromopropane was examined in 1981.[6] 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 feces and the confirmation from maintained blood levels of radioactivity proved the occurrence of biliary excretion of sulfur-containing metabolites and enterohepatic cycling.

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References
  1. "1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012.
  2. 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.
  3. "1,3-Dibromopropane". pubchem.ncbi.nlm.nih.gov.
  4. August Freund (1882). "Ueber Trimethylen". Journal für Praktische Chemie. 26 (1): 367–377. doi:10.1002/prac.18820260125.
  5. 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.
  6. 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.
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