2-Pentyne

2-Pentyne
	Skeletal formula of 2-pentyneSkeletal formula of 2-pentyne
	Ball-and-stick model of 2-pentyneBall-and-stick model of 2-pentyne
Names
	Preferred IUPAC name Pent-2-yne
	Other names Ethylmethylacetylene, 1-Ethyl-2-methylacetylene propyl acetylene
Identifiers
CAS Number	627-21-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	11807 ;
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PubChem CID	12310;
UNII	57NG6HKI9D ;
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	InChI InChI=1S/C5H8/c1-3-5-4-2/h3H2,1-2H3 Key: NKTDTMONXHODTI-UHFFFAOYSA-N ; InChI=1/C5H8/c1-3-5-4-2/h3H2,1-2H3;
	SMILES CC#CCC; C(#CCC)C;
Properties
Chemical formula	C5H8
Molar mass	68.12
Density	0.71 g/mL
Melting point	−109 °C (−164 °F; 164 K)
Boiling point	56 to 57 °C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable Liquid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒ verify (what is Error creating thumbnail: ☒ ?) Infobox references

2-Pentyne, an organic compound with the formula CH₃CH₂C≡CCH₃ and is an internal alkyne. It is an isomer of 1-pentyne, a terminal alkyne.

1-Pentyne

Synthesis

2-Pentyne can be synthesized by the rearrangement 1-pentyne in a solution of ethanolic potassium hydroxide or NaNH2/NH3.^[1]

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v t e 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

Names
Skeletal formula of 2-pentyne Skeletal formula of 2-pentyne
Ball-and-stick model of 2-pentyne Ball-and-stick model of 2-pentyne
Preferred IUPAC name Pent-2-yne
Other names Ethylmethylacetylene, 1-Ethyl-2-methylacetylene propyl acetylene
Identifiers
CAS Number	627-21-4^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	11807^Y
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	12310
UNII	57NG6HKI9D^Y
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
InChI InChI=1S/C5H8/c1-3-5-4-2/h3H2,1-2H3^Y Key: NKTDTMONXHODTI-UHFFFAOYSA-N^Y InChI=1/C5H8/c1-3-5-4-2/h3H2,1-2H3
SMILES CC#CCC C(#CCC)C
Properties
Chemical formula	C₅H₈
Molar mass	68.12
Density	0.71 g/mL
Melting point	−109 °C (−164 °F; 164 K)
Boiling point	56 to 57 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammable Liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is ^{Error creating thumbnail: Y☒N} ?) Infobox references