3-Hexyne

3-Hexyne
Names
	Preferred IUPAC name Hex-3-yne
	Other names Diethylacetylene
Identifiers
CAS Number	928-49-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	12979 ;
ECHA InfoCard	100.011.977
EC Number	213-173-4;
PubChem CID	13568;
UNII	9GTQ990Q4K ;
CompTox Dashboard (EPA)	DTXSID30239144 ;
	InChI InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 Key: DQQNMIPXXNPGCV-UHFFFAOYSA-N ; InChI=1/C6H10/c1-3-5-6-4-2/h3-4H2,1-2H3 Key: DQQNMIPXXNPGCV-UHFFFAOYAF;
	SMILES C(#CCC)CC; CCC#CCC;
Properties
Chemical formula	C6H10
Molar mass	82.14 g/mol
Appearance	Colorless liquid
Density	0.723 g/cm3
Melting point	−105 °C (−157 °F; 168 K)
Boiling point	81 to 82 °C (178 to 180 °F; 354 to 355 K)
Solubility in water	low
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H304, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	−14 °C (7 °F; 259 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]

Structure of the coordination complex NbCl₃(dimethoxyethane)(3-hexyne).^[2]

References

^ Maynard, R. B.; Borodinsky, L.; Grimes, R. N. (1984). "2,3-diethyl-2,3-dicarba- nido -hexaborane(8)". Inorganic Syntheses. Vol. 22. pp. 211–214. doi:10.1002/9780470132531.ch49. ISBN 9780470132531.
^ Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.

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[1] Maynard, R. B.; Borodinsky, L.; Grimes, R. N. (1984). "2,3-diethyl-2,3-dicarba- nido -hexaborane(8)". Inorganic Syntheses. Vol. 22. pp. 211–214. doi:10.1002/9780470132531.ch49. ISBN 9780470132531.

[2] Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.

[1]

[2]

v t e Alkynes
Ethyne (C₂H₂) Propyne (C₃H₄) Butyne (C₄H₆) 1 2 Pentyne (C₅H₈) 1 2 Hexyne (C₆H₁₀) 1 2 3 Heptyne (C₇H₁₂) Octyne (C₈H₁₄) 2 4 Nonyne (C₉H₁₆) Decyne (C₁₀H₁₈) 1 5
Preparations	Cracking Dehydrogenation of alkane, alkene Alkylation of alkynyl anion Dehydrohalogenation of dihaloalkane Fritsch–Buttenberg–Wiechell rearrangement Corey–Fuchs reaction Seyferth–Gilbert homologation
Reactions	Deprotonation Hydrogenation Halogenation Hydration Hydroboration Hydrohalogenation Alkynylation Thiol-yne reaction Alkyne trimerisation Diels–Alder reaction Pauson–Khand reaction Azide-alkyne Huisgen cycloaddition Sonogashira coupling Cadiot–Chodkiewicz coupling Glaser coupling Favorskii reaction