1-Decyne

{{Chembox

| verifiedrevid = 396324541

| Name = 1-Decyne

| ImageFile1 = 1-Decyne.svg

| ImageFile2 = $\backslash scriptstyle\backslash ce\{CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-C\#CH\}$

| ImageSize2 = 300px

| PIN = Dec-1-yne

| OtherNames = 1-Decyne

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|changed|CAS}}

| CASNo = 764-93-2

| ChEBI = 87322

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 12456

| InChI = 1/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3

| InChIKey = ILLHQJIJCRNRCJ-UHFFFAOYAE

| StdInChI = 1S/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3

| StdInChIKey = ILLHQJIJCRNRCJ-UHFFFAOYSA-N

| PubChem = 12997

| EC_number = 212-132-8

| UNII = ULR28GD98Q

| UNII_Ref = {{fdacite|correct|FDA}}

| SMILES = C(#C)CCCCCCCC

}}

|Section2={{Chembox Properties

| C=10 | H=18

| Appearance = Colorless liquid

| Density = 0.767 g/cm³

| MeltingPtC = -44

| BoilingPtC = 174

| RefractIndex = 1.426–1.428

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/DE/1-decyne.html External MSDS]

| NFPA-H =

| NFPA-F =

| NFPA-R =

| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|315|318|335|410}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|362|370+378|391|403+233|403+235|405|501}}

| FlashPtC = 48

| AutoignitionPtC =

}}

|Section8={{Chembox Related

| OtherFunction_label = Alkynes

| OtherFunction = Octyne
Nonyne
Undecyne
Dodecyne

| OtherCompounds = Decane
Decanol
Decene

}}

}}

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,{{cite journal |doi=10.1002/anie.200502017|title=General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water|year=2005|last1=Anderson|first1=Kevin W.|last2=Buchwald|first2=Stephen L.|journal=Angewandte Chemie International Edition|volume=44|issue=38|pages=6173–6177|pmid=16097019}} Huisgen cycloadditions,{{cite journal |doi=10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4|title=A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes|year=2002|last1=Rostovtsev|first1=Vsevolod V.|last2=Green|first2=Luke G.|last3=Fokin|first3=Valery V.|last4=Sharpless|first4=K. Barry|journal=Angewandte Chemie International Edition|volume=41|issue=14|pages=2596–2599|pmid=12203546}} and borylations.{{cite journal |doi=10.1021/ja00076a081|title=Platinum(0)-Catalyzed Diboration of Alkynes|year=1993|last1=Ishiyama|first1=Tatsuo|last2=Matsuda|first2=Nobuo|last3=Miyaura|first3=Norio|last4=Suzuki|first4=Akira|journal=Journal of the American Chemical Society|volume=115|issue=23|pages=11018–11019}}

Under the catalysis of platinum, it reacts with hydrogen to produce decane.{{cite journal|journal=RSC Advances|volume=2|issue=8|language=en|issn=2046-2069|date=2012|pages=3477|doi=10.1039/c2ra01097f|url=http://xlink.rsc.org/?DOI=c2ra01097f|title=Controlled hydrogenation of aromatic compounds by platinum nanowire catalysts|accessdate=2021-11-16|author1=Zhiqiang Guo|author2=Lei Hu|author3=Hsiao-hua Yu|author4=Xueqin Cao|author5=Hongwei Gu|bibcode=2012RSCAd...2.3477G}}