1,3-Dibromopropane

1,3-Dibromopropane

Ball and stick model of 1,3-dibromopropane Spacefill model of 1,3-dibromopropane
Names
Preferred IUPAC name 1,3-Dibromopropane[3]
Other names Trimethylenebromide[1] Trimethylene dibromide[2]
Identifiers
CAS Number	109-64-8^Y
3D model (JSmol)	Interactive image
Beilstein Reference	635662
ChemSpider	7710^Y
ECHA InfoCard	100.003.356
EC Number	203-690-3
MeSH	1,3-dibromopropane
PubChem CID	8001
RTECS number	TX8575000
UNII	YQR3048IX9^Y
UN number	1993
CompTox Dashboard (EPA)	DTXSID1021902
InChI InChI=1S/C3H6Br2/c4-2-1-3-5/h1-3H2^Y Key: VEFLKXRACNJHOV-UHFFFAOYSA-N^Y
SMILES BrCCCBr
Properties
Chemical formula	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)	1.524
Thermochemistry
Heat capacity (C)	163.7 J K mol^−1
Hazards
GHS labelling:
Pictograms
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^−1 (oral, rat)
Related compounds
Related alkanes	1,1-Dibromoethane 1,2-Dibromoethane Tetrabromoethane 1,2-Dibromopropane 1,2,3-Tribromopropane
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 ^YN ?) 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. 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.