1-Pentyne

1-Pentyne^[1]
	Skeletal formula of 1-pentyne
	Ball-and-stick model of 1-pentyne
Names
	Preferred IUPAC name Pent-1-yne
	Other names Propylacetylene
Identifiers
CAS Number	627-19-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL16262 ;
ChemSpider	11806 ;
ECHA InfoCard	100.009.989
PubChem CID	12309;
UNII	EW8XD8E5WF ;
CompTox Dashboard (EPA)	DTXSID7060835 ;
	InChI InChI=1S/C5H8/c1-3-5-4-2/h1H,4-5H2,2H3 Key: IBXNCJKFFQIKKY-UHFFFAOYSA-N ; InChI=1/C5H8/c1-3-5-4-2/h1H,4-5H2,2H3 Key: IBXNCJKFFQIKKY-UHFFFAOYAX;
	SMILES C#CCCC;
Properties
Chemical formula	C5H8
Molar mass	68.12
Appearance	colorless liquid
Density	0.691 g/mL
Melting point	−106 to −105 °C
Boiling point	40.2 °C (104.4 °F; 313.3 K)
Solubility in water	Insoluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable Liquid
Flash point	−20 °C (−4 °F; 253 K)
	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-Pentyne is an organic compound with the formula CH₃CH₂CH₂C≡CH. It is a terminal alkyne, in fact the smallest that is liquid at room temperature. The compound is a common terminal alkyne substrate in diverse studies of catalysis.^[2]^[3]

References

^ 1-Pentyne at Sigma-Aldrich
^ Guimond, Nicolas; Gouliaras, Christina; Fagnou, Keith (2010). "Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N−O Bond as a Handle for C−N Bond Formation and Catalyst Turnover". Journal of the American Chemical Society. 132 (20): 6908–6909. doi:10.1021/ja102571b. PMID 20433170.
^ Cassar, L. (1975). "Synthesis of aryl- and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes". Journal of Organometallic Chemistry. 93 (2): 253–257. doi:10.1016/s0022-328x(00)94048-8.

External links

NIST Chemistry WebBook page for 1-pentyne

[1] 1-Pentyne at Sigma-Aldrich

[2] Guimond, Nicolas; Gouliaras, Christina; Fagnou, Keith (2010). "Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N−O Bond as a Handle for C−N Bond Formation and Catalyst Turnover". Journal of the American Chemical Society. 132 (20): 6908–6909. doi:10.1021/ja102571b. PMID 20433170.

[3] Cassar, L. (1975). "Synthesis of aryl- and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes". Journal of Organometallic Chemistry. 93 (2): 253–257. doi:10.1016/s0022-328x(00)94048-8.

[1]

[2]

[3]

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

External links