1-Butyne

1-Butyne
Names
	Preferred IUPAC name But-1-yne
	Other names Ethylacetylene; Ethylethyne, UN 2452
Identifiers
CAS Number	107-00-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48087 ;
ChemSpider	7558 ;
ECHA InfoCard	100.003.139
EC Number	203-451-3;
PubChem CID	7846;
UNII	A6B47CPN6W ;
UN number	2452
CompTox Dashboard (EPA)	DTXSID4029141 ;
	InChI InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYSA-N ; InChI=1/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYAI;
	SMILES C#CCC;
Properties
Chemical formula	C4H6
Molar mass	54.091 g/mol
Density	0.6783 g cm−3
Melting point	−125.7 °C (−194.3 °F; 147.5 K)
Boiling point	8.08 °C (46.54 °F; 281.23 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
	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-Butyne is an organic compound with the formula CH₃CH₂C≡CH. It is a terminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustible gas.^[1]

1-Butyne participates in reactions typical for terminal alkynes, such as alkyne metathesis,^[2] hydrogenation, condensation with formaldehyde. Based on its heat of combustion, it is slightly more stable than its isomer 2-butyne.^[3]

References

^ ^a ^b ^c ^d ^e Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–84. ISBN 978-0-8493-0488-0.
^ Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. (2004). "Highly Active Trialkoxymolybdenum(VI) Alkylidyne Catalysts Synthesized by a Reductive Recycle Strategy". Journal of the American Chemical Society. 126 (1): 329–335. doi:10.1021/ja0379868. PMID 14709099.
^ Prosen, E.J.; Maron, F.W.; Rossini, F.D. (1951). "Heats of combustion, formation, and insomerization of ten C4 hydrocarbons". Journal of Research of the National Bureau of Standards. 46 (2): 106. doi:10.6028/jres.046.015.

External links

NIST Chemistry WebBook page for 1-butyne

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[CRC-1] Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–84. ISBN 978-0-8493-0488-0.

[2] Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. (2004). "Highly Active Trialkoxymolybdenum(VI) Alkylidyne Catalysts Synthesized by a Reductive Recycle Strategy". Journal of the American Chemical Society. 126 (1): 329–335. doi:10.1021/ja0379868. PMID 14709099.

[3] Prosen, E.J.; Maron, F.W.; Rossini, F.D. (1951). "Heats of combustion, formation, and insomerization of ten C4 hydrocarbons". Journal of Research of the National Bureau of Standards. 46 (2): 106. doi:10.6028/jres.046.015.

[1]

[2]

[3]

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
${\ce {H-C#C}}{-}{\ce {\overset {\displaystyle {H} \atop \|}{\underset {\| \atop \displaystyle {H}}{C}}}}{-}{\ce {\overset {\displaystyle {H} \atop \|}{\underset {\| \atop \displaystyle {H}}{C}}}}{\ce {-H}}$


Preferred IUPAC name But-1-yne
Other names Ethylacetylene Ethylethyne, UN 2452
Identifiers
CAS Number	107-00-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48087^Y
ChemSpider	7558^Y
ECHA InfoCard	100.003.139
EC Number	203-451-3
PubChem CID	7846
UNII	A6B47CPN6W^Y
UN number	2452
CompTox Dashboard (EPA)	DTXSID4029141
InChI InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3^Y Key: KDKYADYSIPSCCQ-UHFFFAOYSA-N^Y InChI=1/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYAI
SMILES C#CCC
Properties^[1]
Chemical formula	C₄H₆
Molar mass	54.091 g/mol
Density	0.6783 g cm⁻³^[1]
Melting point	−125.7 °C (−194.3 °F; 147.5 K)^[1]
Boiling point	8.08 °C (46.54 °F; 281.23 K)^[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

1-Butyne

See also

References

External links