1,3-Dibromopropane
Skeletal formula of 1,3-dibromopropane
Ball and stick model of 1,3-dibromopropane
Ball and stick model of 1,3-dibromopropane
Spacefill model of 1,3-dibromopropane
Spacefill model of 1,3-dibromopropane
Names
Preferred 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
  • InChI=1S/C3H6Br2/c4-2-1-3-5/h1-3H2 checkY
    Key: VEFLKXRACNJHOV-UHFFFAOYSA-N checkY
  • BrCCCBr
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 labelling:
GHS02: Flammable GHS07: Exclamation mark GHS09: Environmental hazard
Warning
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).
☒N verify (what is checkY☒N ?)
Infobox references

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 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 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

  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. PMID 7245244.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.