| Revision as of 16:22, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,294 edits Saving copy of the {{chembox}} taken from revid 456618308 of page 1,3-Dibromopropane for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 21:09, 17 March 2022 edit DMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators187,229 editsm Reverted edits by 85.210.61.180 (talk) to last version by WprlhTag: Rollback |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443341251 |
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| verifiedrevid = 477205174 |
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| ImageFile = 1%2C3-Dibrompropan.png |
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| ImageFile = 1,3-dibromopropane_200.svg |
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| ImageSize = 200px |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = 1,3-dibromopropane |
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| ImageSize = 180 |
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| IUPACName = 1,3-dibromopropane |
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| ImageName = Skeletal formula of 1,3-dibromopropane |
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| OtherNames = trimethylene dibromide |
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| ImageFileL1 = 1,3-Dibromopropane-3D-balls.png |
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| OtherNames = trimethylenebromide |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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| ImageNameL1 = Ball and stick model of 1,3-dibromopropane |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ImageFileR1 = 1,3-Dibromopropane-3D-spacefill.png |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageNameR1 = Spacefill model of 1,3-dibromopropane |
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| PIN = 1,3-Dibromopropane<ref>{{Cite web|title=1,3-dibromopropane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8001&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=21 June 2012|location=USA|date=26 March 2005|at=Identification}}</ref> |
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| OtherNames = {{Unbulleted list|Trimethylenebromide<ref>{{cite book |last1=Creese |first1=Mary R. S. |title=Ladies in the Laboratory IV: Imperial Russia's Women in Science, 1800-1900: A Survey of Their Contributions to Research |date=2015 |publisher=Rowman & Littlefield |isbn=978-1-4422-4742-0 |page=57 |url=https://books.google.com/books?id=m1RuBwAAQBAJ&pg=PA57 |language=en}}</ref>|Trimethylene dibromide<ref>{{cite web |title=1,3-Dibromopropane |url=https://pubchem.ncbi.nlm.nih.gov/compound/8001 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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}} |
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|Section1={{Chembox Identifiers |
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| CASNo = 109-64-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 8001 |
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| ChemSpiderID = 7710 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = YQR3048IX9 |
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| UNII = YQR3048IX9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-690-3 |
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| UNNumber = 1993 |
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| MeSHName = 1,3-dibromopropane |
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| RTECS = TX8575000 |
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| Beilstein = 635662 |
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| SMILES = BrCCCBr |
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| SMILES = BrCCCBr |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7710 |
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| InChI = 1/C3H6Br2/c4-2-1-3-5/h1-3H2 |
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| InChIKey = VEFLKXRACNJHOV-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H6Br2/c4-2-1-3-5/h1-3H2 |
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| StdInChI = 1S/C3H6Br2/c4-2-1-3-5/h1-3H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VEFLKXRACNJHOV-UHFFFAOYSA-N |
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| StdInChIKey = VEFLKXRACNJHOV-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 109-64-8 |
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|Section2={{Chembox Properties |
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| RTECS = |
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| C=3 | H=6 | Br=2 |
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}} |
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| Appearance = Colorless liquid |
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| Section2 = {{Chembox Properties |
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| Density = 1.989 g mL<sup>−1</sup> |
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| Formula = C<sub>3</sub>H<sub>6</sub>Br<sub>2</sub> |
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| MolarMass = 201.89 g/mol |
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| MeltingPtK = 238.95 |
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| BoilingPtK =440 |
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| Appearance = Colorless to slightly-yellow liquid |
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| HenryConstant = 11 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| Density = 1.98 g/mL, liquid |
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| RefractIndex = 1.524 |
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| Solubility = |
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}} |
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| MeltingPtC = -34 |
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|Section3={{Chembox Thermochemistry |
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| BoilingPt = 166-167 °C (439 - 440 K) |
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| HeatCapacity = 163.7 J K mol<sup>−1</sup> |
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| Viscosity = |
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| Section3 = {{Chembox Structure |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS environment}} |
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| Dipole = |
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| GHSSignalWord = '''WARNING''' |
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| HPhrases = {{H-phrases|226|302|315|411}} |
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| Section7 = {{Chembox Hazards |
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| PPhrases = {{P-phrases|273}} |
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| GHSPictograms = {{GHSp|GHS02}}{{GHSp|GHS07}}{{GHSp|GHS09}}<ref name="sigma">{{SigmaLink |
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| Productgroup = Fluka |
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| FlashPtC = 56 |
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| LD50 = 315 mg kg<sup>−1</sup> <small>(oral, rat)</small> |
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| Productcode = 34280 |
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}} |
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| Accessdate = June 10, 2011 |
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|Section5={{Chembox Related |
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}}</ref> |
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| OtherFunction_label = alkanes |
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| HPhrases = {{H-phrases|226|302|315|411}}<ref name="sigma" /> |
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| OtherFunction = {{Unbulleted list|]|]|]|]|]}} |
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| PPhrases = {{P-phrases|273}} |
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| OtherCompounds = ] |
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| MainHazards = |
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| FlashPt = 56 °C (closed cup) |
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| RPhrases = {{R10}} {{R22}} {{R38}} {{R51}} {{R53}} |
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| SPhrases = {{S16}} {{S26}} {{S36}} {{S61}} |
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| Section8 = {{Chembox Related |
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| Function = |
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'''1,3-Dibromopropane''' is an ] with the formula (CH<sub>2</sub>)<sub>3</sub>Br<sub>2</sub>. It is a colorless liquid with sweet odor. It is used in ] to form C<sub>3</sub>-bridged compounds such as through C-N coupling reactions. |
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1,3-Dibromopropane was used in the first ] synthesis in 1881, known as the ].<ref name=Freund81>{{cite journal | author = August Freund | title = Ueber Trimethylen | journal = Journal für Praktische Chemie | year = 1882 | volume = 26 | issue = 1 | pages = 367–377 | doi = 10.1002/prac.18820260125 | url = https://zenodo.org/record/1427896 }}</ref> |
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==Synthesis== |
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1,3-Dibromopropane can be prepared via the ] between ] and ].<ref>{{cite journal | author = W. E. Vaughan | author2 = F. F. Rust | author3 = T. W. Evans | title = The photo-addition of hydrogen bromide to olefinic bonds | journal = ] | year = 1942 | volume = 7 | issue = 6 | pages = 477–490 | doi = 10.1021/jo01200a005 }}</ref> |
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] |
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==Metabolism== |
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Metabolism of 1,3-dibromopropane was examined in 1981.<ref>{{cite journal | author = S. P. James | author2 = M. A. Put | author3 = D. H. Richards | title = Metabolism of 1,3-dibromopropane | journal = Toxicology Letters | year = 1981 | volume = 8 | issue = 1–2 | pages = 7–15 | doi = 10.1016/0378-4274(81)90130-2 | pmid = 7245244 }}</ref> 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. |
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==References== |
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{{Reflist}} |
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{{Authority control}} |
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{{DEFAULTSORT:Dibromopropane, 1, 3-}} |
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] |