2-Hexyne

2-Hexyne
Names
	Preferred IUPAC name Hex-2-yne
Identifiers
CAS Number	764-35-2;
3D model (JSmol)	Interactive image;
ChemSpider	31016;
ECHA InfoCard	100.011.015
EC Number	212-117-6;
PubChem CID	33629;
UNII	EC0WA2IXU7;
CompTox Dashboard (EPA)	DTXSID9074725 ;
	InChI InChI=1S/C6H10/c1-3-5-6-4-2/h3,5H2,1-2H3 Key: MELUCTCJOARQQG-UHFFFAOYSA-N;
	SMILES CCCC#CC;
Properties
Chemical formula	C6H10
Molar mass	82.146 g·mol−1
Density	0.7317
Melting point	−88 °C (−126 °F; 185 K)
Boiling point	83.8 °C (182.8 °F; 356.9 K)
Refractive index (nD)	1.4135
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H304, H315, H319
Precautionary statements	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	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.

[1] 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.

[henn-2] 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.

[3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] 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.

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