| Revision as of 17:50, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465793070 of page 3-Hexyne for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:02, 1 September 2023 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,617 edits →Synthesis and reactions: n-butyl, not N-butyl |
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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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{{chembox |
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| ImageFile1 = Hex-1-yne.png |
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| verifiedrevid = 440494426 |
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| ImageFile1=Hex-3-yne-2D-skeletal.png |
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| ImageFile2 = 1-Hexyne-3D-vdW.png |
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| OtherNames = ''n''-Butylacetylene |
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| ImageSize1=180px |
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| PIN = Hex-1-yne |
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| ImageName1=Skeletal formula |
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| Section1 = {{Chembox Identifiers |
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| ImageFile2=3-hexyne-3D-balls.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageSize2=180px |
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| ChemSpiderID = 12209 |
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| ImageName2=Ball-and-stick model |
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| ChEBI = 176793 |
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| IUPACName=Hex-3-yne |
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| EINECS = 211-736-9 |
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| OtherNames=Diethylacetylene |
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| InChI = 1S/C6H10/c1-3-5-6-4-2/h1H,4-6H2,2H3 |
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| Section1= {{Chembox Identifiers |
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| InChIKey = CGHIBGNXEGJPQZ-UHFFFAOYSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 12979 |
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| SMILES1 = CCCCC#C |
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| CASNo= 693-02-7 |
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| InChI = 1/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| InChIKey = DQQNMIPXXNPGCV-UHFFFAOYAF |
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| SMILES1 = CCC#CCC |
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| UNII = 5FZF2F38F5 |
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| PubChem=12732 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DQQNMIPXXNPGCV-UHFFFAOYSA-N |
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| CASNo=928-49-4 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem=13568 |
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| SMILES = C(#CCC)CC |
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}} |
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|Section2= {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=6 | H=10 |
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| Formula=C<sub>6</sub>H<sub>10</sub> |
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| MolarMass=82.14 g/mol |
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<!--n20/D 1.411--> |
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<!--n20/D 1.411--> |
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| Appearance= Colorless liquid |
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| Appearance= colorless liquid<br/>(impure samples can appear yellowish) |
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| Density=0.723 g/cm<sup>3</sup> |
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| Density=0.72 g/cm<sup>3</sup> |
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| MeltingPtC = -105 |
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| MeltingPtC = -132 |
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| BoilingPtC = 71 to 72 |
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| BoilingPtCL = 81 |
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| Solubility= 0.36 g/L |
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| BoilingPtCH = 82 |
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| Solubility=low |
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|Section3= {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = Irritant, Flammable, Health Hazard |
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| ExternalMSDS = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-H = |
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| NFPA-R = |
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| NFPA-F = |
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| NFPA-R = |
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| FlashPt = -14 °C, 259 K |
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| FlashPtC = -20 |
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| RPhrases = {{R11}} {{R36/37/38}} {{R65}} |
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| AutoignitionPtC = |
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| SPhrases = {{S16}} {{S26}} {{S36}} {{S62}} |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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| Autoignition= |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|225|304|315|319|335}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|301+310|302+352|303+361+353|304+340|305+351+338|312|321|331|332+313|337+313|362|370+378|403+233|403+235|405|501}} |
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| Watchedfields = changed |
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| verifiedrevid = 477218540 |
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'''1-Hexyne ''' is a ] consisting of a ] six-] chain having a ]. Its ] is {{chem2|HC2C4H9}}. A colorless liquid, it is one of three isomers of hexyne.<ref name=OS/> It is used as a reagent in organic synthesis. |
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== Synthesis and reactions == |
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1-Hexyne can be prepared by the reaction of ] with ]:<ref name=OS>{{cite journal |author=Kenneth N. Campbell, Barbara K. Campbell|doi=10.15227/orgsyn.030.0015|title=''n''-Butylacetylene |journal=Organic Syntheses |year=1950 |volume=30 |page=15 }}</ref> |
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:{{chem2|NaC2H + BrC4H9 -> HC2C4H9 + NaBr}} |
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Its reactivity illustrates the behavior of terminal alkylacetylenes. The hexyl derivative is common test substrate because it is conveniently volatile. It undergoes deprotonation at C-3 and C-1 with ]: |
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:{{chem2|HC2C4H9 + 2 BuLi -> LiC2CH(Li)C3H7 + 2 BuH}} |
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This reaction allows alkylation at the 3-position.<ref>{{cite journal |doi=10.15227/orgsyn.058.0001|author=A. J. Quillinan, F. Scheinmann|title=3-Alkyl-1-Alkynes Synthesis: 3-Ethyl-1-Hexyne |journal=Organic Syntheses |year=1978 |volume=58 |page=1 }}</ref> |
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Catechol borane adds to 1-hexyne to give the 1-hexenyl borane. |
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<ref>{{cite journal |doi=10.15227/orgsyn.068.0130|author=Norio Miyaura Akira Suzuki|title=Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene |journal=Organic Syntheses |year=1990 |volume=68 |page=130 }}</ref> |
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1-Hexyne reacts with diethyl ] to produce {{chem name|''n''-hexylsuccinic acid}}.<ref>{{Cite journal|last1=Hogsed|first1=M. J.|last2=Lindsey|first2=R. V.|date=1953-10-01|title=The Reaction of 1-Hexyne and Diethyl Fumarate|url=https://doi.org/10.1021/ja01115a517|journal=Journal of the American Chemical Society|volume=75|issue=19|pages=4846–4847|doi=10.1021/ja01115a517|issn=0002-7863}}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Hexyne, 1-}} |
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] |