3-Hexyne
{{chembox
| Watchedfields = changed
| verifiedrevid = 477218540
| ImageFile1=Hex-3-yne-2D-skeletal.png
| ImageSize1=180px
| ImageName1=Skeletal formula
| ImageFile2=3-hexyne-3D-balls.png
| ImageSize2=180px
| ImageName2=Ball-and-stick model
| PIN=Hex-3-yne
| OtherNames=Diethylacetylene
| Section1= {{Chembox Identifiers
| CASNo=928-49-4
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12979
| EC_number = 213-173-4
| PubChem=13568
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9GTQ990Q4K
| InChI = 1/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3
| InChIKey = DQQNMIPXXNPGCV-UHFFFAOYAF
| SMILES1 = CCC#CCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DQQNMIPXXNPGCV-UHFFFAOYSA-N
| SMILES = C(#CCC)CC
}}
|Section2= {{Chembox Properties
| Formula=C6H10
| MolarMass=82.14 g/mol
| Appearance= Colorless liquid
| Density=0.723 g/cm3
| MeltingPtC = -105
| BoilingPtC = 81 to 82
| Solubility=low
}}
|Section3= {{Chembox Hazards
| ExternalSDS =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| FlashPtC = -14
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|304|315|319|335}}
| 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}}
| AutoignitionPtC =
}}
}}
3-Hexyne is the organic compound with the formula C2H5CCC2H5. This colorless liquid is one of three isomeric hexynes. 3-Hexyne forms with 5-decyne, 4-octyne, and 2-butyne a series of symmetric alkynes. It is a reagent in organometallic chemistry.{{cite book |doi=10.1002/9780470132531.ch49|title=Inorganic Syntheses|year=1984|last1=Maynard|first1=R. B.|last2=Borodinsky|first2=L.|last3=Grimes|first3=R. N.|chapter=2,3-diethyl-2,3-dicarba- nido -hexaborane(8) |pages=211–214|volume=22|isbn=9780470132531}}
file:NbCl3(dme)(hexyne).png NbCl3(dimethoxyethane)(3-hexyne).{{cite journal |doi=10.1021/ja8100837|title=New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism|year=2009|last1=Arteaga-Müller|first1=Rocío|last2=Tsurugi|first2=Hayato|last3=Saito|first3=Teruhiko|last4=Yanagawa|first4=Masao|last5=Oda|first5=Seiji|last6=Mashima|first6=Kazushi|journal=Journal of the American Chemical Society|volume=131|issue=15|pages=5370–5371|pmid=20560633}}]]
