1-Decyne

1-Decyne
Names
	Preferred IUPAC name Dec-1-yne
	Other names 1-Decyne
Identifiers
CAS Number	764-93-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:87322;
ChemSpider	12456 ;
ECHA InfoCard	100.011.029
EC Number	212-132-8;
PubChem CID	12997;
UNII	ULR28GD98Q ;
CompTox Dashboard (EPA)	DTXSID60870766 ;
	InChI InChI=1S/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3 Key: ILLHQJIJCRNRCJ-UHFFFAOYSA-N; InChI=1/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3 Key: ILLHQJIJCRNRCJ-UHFFFAOYAE;
	SMILES C(#C)CCCCCCCC;
Properties
Chemical formula	C10H18
Molar mass	138.254 g·mol−1
Appearance	Colorless liquid
Density	0.767 g/cm3
Melting point	−44 °C (−47 °F; 229 K)
Boiling point	174 °C (345 °F; 447 K)
Refractive index (nD)	1.426–1.428
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H315, H318, H335, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	48 °C (118 °F; 321 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related Alkynes	Octyne; Nonyne; Undecyne; Dodecyne
Related compounds	Decane; Decanol; Decene
	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

1-Decyne is the organic compound with the formula C₈H₁₇C≡CH. It is a terminal alkyne. A colorless liquid, 1-decyne is used as a model substrate when evaluating methodology in organic synthesis. It participates in a number of classical reactions including Suzuki-Miyaura couplings, Sonogashira couplings,^[1] Huisgen cycloadditions,^[2] and borylations.^[3]

Under the catalysis of platinum, it reacts with hydrogen to produce decane.^[4]

References

^ Anderson, Kevin W.; Buchwald, Stephen L. (2005). "General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water". Angewandte Chemie International Edition. 44 (38): 6173–6177. doi:10.1002/anie.200502017. PMID 16097019.
^ Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V.; Sharpless, K. Barry (2002). "A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes". Angewandte Chemie International Edition. 41 (14): 2596–2599. doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. PMID 12203546.
^ Ishiyama, Tatsuo; Matsuda, Nobuo; Miyaura, Norio; Suzuki, Akira (1993). "Platinum(0)-Catalyzed Diboration of Alkynes". Journal of the American Chemical Society. 115 (23): 11018–11019. doi:10.1021/ja00076a081.
^ Zhiqiang Guo; Lei Hu; Hsiao-hua Yu; Xueqin Cao; Hongwei Gu (2012). "Controlled hydrogenation of aromatic compounds by platinum nanowire catalysts". RSC Advances. 2 (8): 3477. Bibcode:2012RSCAd...2.3477G. doi:10.1039/c2ra01097f. ISSN 2046-2069. Retrieved 2021-11-16.

[1] Anderson, Kevin W.; Buchwald, Stephen L. (2005). "General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water". Angewandte Chemie International Edition. 44 (38): 6173–6177. doi:10.1002/anie.200502017. PMID 16097019.

[2] Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V.; Sharpless, K. Barry (2002). "A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes". Angewandte Chemie International Edition. 41 (14): 2596–2599. doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. PMID 12203546.

[3] Ishiyama, Tatsuo; Matsuda, Nobuo; Miyaura, Norio; Suzuki, Akira (1993). "Platinum(0)-Catalyzed Diboration of Alkynes". Journal of the American Chemical Society. 115 (23): 11018–11019. doi:10.1021/ja00076a081.

[4] Zhiqiang Guo; Lei Hu; Hsiao-hua Yu; Xueqin Cao; Hongwei Gu (2012). "Controlled hydrogenation of aromatic compounds by platinum nanowire catalysts". RSC Advances. 2 (8): 3477. Bibcode:2012RSCAd...2.3477G. doi:10.1039/c2ra01097f. ISSN 2046-2069. Retrieved 2021-11-16.

[1]

[2]

[3]

[4]

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

See also

References