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1,3-Dibromopropane

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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
Other names
  • Trimethylenebromide
  • Trimethylene dibromide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 635662
ChemSpider
ECHA InfoCard 100.003.356 Edit this at Wikidata
EC Number
  • 203-690-3
MeSH 1,3-dibromopropane
PubChem CID
RTECS number
  • TX8575000
UNII
UN number 1993
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6Br2/c4-2-1-3-5/h1-3H2Key: VEFLKXRACNJHOV-UHFFFAOYSA-N
SMILES
  • BrCCCBr
Properties
Chemical formula C3H6Br2
Molar mass 201.889 g·mol
Appearance Colorless liquid
Density 1.989 g mL
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 kg
Refractive index (nD) 1.524
Thermochemistry
Heat capacity (C) 163.7 J K mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS07: Exclamation mark GHS09: Environmental hazard
Signal word Warning
Hazard statements H226, H302, H315, H411
Precautionary statements P273
Flash point 56 °C (133 °F; 329 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 315 mg kg (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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Synthesis

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

Metabolism

Metabolism of 1,3-dibromopropane was examined in 1981. 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. 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.
  2. "1,3-Dibromopropane". pubchem.ncbi.nlm.nih.gov.
  3. "1,3-dibromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 21 June 2012.
  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.
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