2-Hexyne
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Names | |
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Preferred IUPAC name
Hex-2-yne | |
Identifiers | |
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3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.011.015 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C6H10 | |
Molar mass | 82.146 g·mol−1 |
Density | 0.7317 |
Melting point | −88 °C (−126 °F; 185 K)[1] |
Boiling point | 83.8 °C (182.8 °F; 356.9 K)[2] |
Refractive index (nD)
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1.4135 |
Hazards | |
GHS labelling: | |
Signal word
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Danger |
H225, H304, H315, H319 | |
P210, P233, P240, P241, P242, P243, P264, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, P501 | |
Related compounds | |
Related compounds
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3-Hexyne, 1-Hexyne |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
2-Hexyne is an organic compound that belongs to the alkyne group. Just like its isomers, it also has the chemical formula of C6H10.
Reactions[]
2-Hexyne can be semihydrogenated to yield or fully hydrogenated to hexane.[3] With appropriate noble metal catalysts it can selectively form cis-2-hexene.[4]
2-Hexyne can act as a ligand on gold atoms.[5]
With strong sulfuric acid, the ketone 2-hexanone is produced. However this reaction also causes polymerization and charring.[6]
Under heat and pressure 2-hexyne polymerizes to linear oligomers and polymers. This can be hastened by some catalysts such as molybdenum pentachloride with . However Ziegler–Natta catalysts have no action as the triple bond is hindered.[7]
References[]
- ^ Campbell, Kenneth N.; Eby, Lawrence T. (October 1941). "The Reduction of Multiple Carbon—Carbon Bonds. III. Further Studies on the Preparation of Olefins from Acetylenes 1,2". Journal of the American Chemical Society. 63 (10): 2683–2685. doi:10.1021/ja01855a050.
- ^ Hennion, G. F.; Sheehan, J. J. (June 1949). "1,2-Hexadiene". Journal of the American Chemical Society. 71 (6): 1964–1966. doi:10.1021/ja01174a017.
- ^ Ulan, Judith G.; Maier, Wilhelm F. (September 1989). "Mechanism of 2-hexyne hydrogenation on heterogeneous palladium". Journal of Molecular Catalysis. 54 (2): 243–261. doi:10.1016/0304-5102(89)80220-2.
- ^ Schrock, Richard R.; Osborn, John A. (April 1976). "Catalytic hydrogenation using cationic rhodium complexes. II. The selective hydrogenation of alkynes to cis olefins". Journal of the American Chemical Society. 98 (8): 2143–2147. doi:10.1021/ja00424a021.
- ^ Zuccaccia, Daniele; Belpassi, Leonardo; Rocchigiani, Luca; Tarantelli, Francesco; Macchioni, Alceo (5 April 2010). "A Phosphine Gold(I) π-Alkyne Complex: Tuning the Metal−Alkyne Bond Character and Counterion Position by the Choice of the Ancillary Ligand". Inorganic Chemistry. 49 (7): 3080–3082. doi:10.1021/ic100093n.
- ^ Thomas, Robert J.; Campbell, Kenneth N.; Hennion, G. F. (March 1938). "Catalytic Hydration of Alkylacetylenes 1". Journal of the American Chemical Society. 60 (3): 718–720. doi:10.1021/ja01270a061.
- ^ Higashimura, Toshinobu; Deng, Yun Xiang; Masuda, Toshio (March 1982). "Polymerization of 2-hexyne and higher 2-alkynes catalyzed by MoCl 5 Ph 4 Sn and WCl 6 Ph 4 Sn 1". Macromolecules. 15 (2): 234–238. doi:10.1021/ma00230a005.
Categories:
- Alkynes