1,3-Dibromopropane

changed changed 477205174 1,3-dibromopropane_200.svg correct ?? 180 Skeletal formula of 1,3-dibromopropane 1,3-Dibromopropane-3D-balls.png correct ?? Ball and stick model of 1,3-dibromopropane 1,3-Dibromopropane-3D-spacefill.png correct ?? Spacefill model of 1,3-dibromopropane 1,3-Dibromopropane1,3-dibromopropane - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/8001 PubChem Compound National Center for Biotechnology Information 21 June 2012 USA 26 March 2005 Identification TrimethylenebromideCreese Mary R. S. Ladies in the Laboratory IV: Imperial Russia's Women in Science, 1800-1900: A Survey of Their Contributions to Research 2015 Rowman & Littlefield 978-1-4422-4742-0 57 https://books.google.com/books?id=m1RuBwAAQBAJ&pg=PA57 en Trimethylene dibromide1,3-Dibromopropane https://pubchem.ncbi.nlm.nih.gov/compound/8001 pubchem.ncbi.nlm.nih.gov en 109-64-8 correct CAS 8001 7710 correct chemspider YQR3048IX9 correct FDA 203-690-3 1993 1,3-dibromopropane TX8575000 635662 BrCCCBr 1S/C3H6Br2/c4-2-1-3-5/h1-3H2 correct chemspider VEFLKXRACNJHOV-UHFFFAOYSA-N correct chemspider 3 6 2 Colorless liquid 1.989 g mL−1 238.95 440 11 μmol Pa−1 kg−1 1.524 163.7 J K mol−1 flame exclamation mark environment WARNING 226 302 315 411 273 56 315 mg kg−1 (oral, rat) alkanes 1,1-Dibromoethane 1,2-Dibromoethane Tetrabromoethane 1,2-Dibromopropane 1,2,3-Tribromopropane Mitobronitol 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. August Freund Ueber Trimethylen Journal für Praktische Chemie 1882 26 1 367–377 10.1002/prac.18820260125 https://zenodo.org/record/1427896 Synthesis 1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide. W. E. Vaughan F. F. Rust T. W. Evans The photo-addition of hydrogen bromide to olefinic bonds Journal of Organic Chemistry 1942 7 6 477–490 10.1021/jo01200a005 center Metabolism Metabolism of 1,3-dibromopropane was examined in 1981. S. P. James M. A. Put D. H. Richards Metabolism of 1,3-dibromopropane Toxicology Letters 1981 8 1–2 7–15 10.1016/0378-4274(81)90130-2 7245244 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 Category:Bromoalkanes Category:1,3-Propanediyl compounds