2-Octyne

2-Octyne
Names
	Preferred IUPAC name Oct-2-yne
	Other names Amylmethylacetylene; Methylpentylacetylene
Identifiers
CAS Number	2809-67-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	16791;
EC Number	220-553-3;
PubChem CID	17769;
UNII	YP28K987X2 ;
	InChI InChI=1S/C8H14/c1-3-5-7-8-6-4-2/h3,5,7-8H2,1-2H3 Key: QCQALVMFTWRCFI-UHFFFAOYSA-N; InChI=1/C8H14/c1-3-5-7-8-6-4-2/h3,5,7-8H2,1-2H3 Key: QCQALVMFTWRCFI-UHFFFAOYAD;
	SMILES CC#CCCCCC;
Properties
Chemical formula	C8H14
Molar mass	110.200 g·mol−1
Density	0.759 g/mL
Boiling point	137 °C (279 °F; 410 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2-Octyne, also known as methylpentylethin and oct-2-yne,^[1] is a type of alkyne with a triple bond at its second carbon (the '2-' indicates the location of the triple bond in the chain). Its formula is C₈H₁₄.^[2] Its density at 25 °C and otherwise stable conditions is 0.759 g/ml.^[3] The boiling point is 137 °C.^[3] The average molar mass is 110.20 g/mol.^[2]

It is formed by isomerization of 1-octyne catalyzed by a Yb^II complex.^[4]

References

↑ "2-OCTYNE | C8H14 - PubChem". https://pubchem.ncbi.nlm.nih.gov/compound/2-octyne. Retrieved 16 August 2016.
↑ ^2.0 ^2.1 Rogers, D. W.; Dagdagan, O. A.; Allinger, N. L. (1979). "webbook.nist.gov/cgi/cbook.cgi". pp. 671–676. http://webbook.nist.gov/cgi/cbook.cgi?ID=C2809678&Mask=8. Retrieved 16 August 2016.
↑ ^3.0 ^3.1 Sigma-Aldrich Co., 2-Octyne. Retrieved on 16 August 2016.
↑ Makioka, Yoshikazu; Taniguchi, Yuki; Kitamura, Tsugio; Fujiwara, Yuzo; Saiki, Akira; Takaki, Ken. Isomerization of terminal alkynes catalyzed by ytterbium(II)-aromatic imine complexes. Bulletin de la Societe Chimique de France, 1997. Volume 134. (3&4) pp 349-355.

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Original source: https://en.wikipedia.org/wiki/2-Octyne. Read more

[pubchem-1] "2-OCTYNE | C8H14 - PubChem". https://pubchem.ncbi.nlm.nih.gov/compound/2-octyne. Retrieved 16 August 2016.

[nist-2] 2.0 ^2.1 Rogers, D. W.; Dagdagan, O. A.; Allinger, N. L. (1979). "webbook.nist.gov/cgi/cbook.cgi". pp. 671–676. http://webbook.nist.gov/cgi/cbook.cgi?ID=C2809678&Mask=8. Retrieved 16 August 2016.

[Sigma-3] 3.0 ^3.1 Sigma-Aldrich Co., 2-Octyne. Retrieved on 16 August 2016.

[4] Makioka, Yoshikazu; Taniguchi, Yuki; Kitamura, Tsugio; Fujiwara, Yuzo; Saiki, Akira; Takaki, Ken. Isomerization of terminal alkynes catalyzed by ytterbium(II)-aromatic imine complexes. Bulletin de la Societe Chimique de France, 1997. Volume 134. (3&4) pp 349-355.

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v t e Alkynes
Ethyne ( C₂H₂ ) Propyne ( C₃H₄ ) Butyne ( C₄H₆ ) 1 2 Pentyne ( C₅H₈ ) 1 2 Hexyne ( C₆H₁₀ ) Heptyne ( C₇H₁₂ ) Octyne ( C₈H₁₄ ) 2 4 Nonyne ( C₉H₁₆ ) Decyne ( C₁₀H₁₈ ) 1 5
Preparations	Cracking [[Chemistry:DehydrogenatDehydrogenation]] 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 Thiol-yne reaction Alkyne trimerisation Diels–Alder reaction Pauson–Khand reaction Azide-alkyne Huisgen cycloaddition Sonogashira coupling Cadiot–Chodkiewicz coupling Glaser coupling Favorskii reaction