1-Decyne

1-Decyne
Names
Preferred IUPAC name
Dec-1-yne
Other names
1-Decyne
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.029 Edit this at Wikidata
EC Number
  • 212-132-8
UNII
  • 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
  • C(#C)CCCCCCCC
Properties
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)
1.426–1.428
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H226, H315, H318, H335, H410
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).
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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]

  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.