2-Butene

2-Butene
source ↗ cis	source ↗ trans
source ↗ cis	source ↗ trans
Names
	Preferred IUPAC name But-2-ene
	Other names β-Butylene
Identifiers
CAS Number	107-01-7 Y; (cis): 590-18-1 Y; (trans): 624-64-6 Y;
3D model (JSmol)	Interactive image; (cis): Interactive image; (trans): Interactive image;
Beilstein Reference	1718755 1361341
ChEBI	CHEBI:48363 Y; (cis): CHEBI:48366; (trans): CHEBI:48365;
ChemSpider	11719 Y; (cis): 4449912 N; (trans): 56442 N;
ECHA InfoCard	100.003.140
EC Number	203-452-9;
Gmelin Reference	25196 1140 1141
PubChem CID	(cis): 5287573; (trans): 62695;
RTECS number	EM2932000 1718756;
UNII	S1SK37516R Y; (cis): L35ORC9C05 Y; (trans): 017NGL487F Y;
CompTox Dashboard (EPA)	DTXSID1026748 ;
	InChI InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3 Y Key: IAQRGUVFOMOMEM-UHFFFAOYSA-N Y; InChI=1/C4H8/c1-3-4-2/h3-4H,1-2H3 Key: IAQRGUVFOMOMEM-UHFFFAOYAW; (cis): InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3- Key: IAQRGUVFOMOMEM-ARJAWSKDSA-N; (trans): InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3/b4-3+ Key: IAQRGUVFOMOMEM-ONEGZZNKSA-N;
	SMILES C(=CC)C; (cis): C/C=C\C; (trans): C/C=C/C;
Properties
Chemical formula	C4H8
Molar mass	56.108 g·mol−1
Density	0.641 g/ml (cis, 3.7 °C); 0.626 g/ml (trans, 0.9 °C)
Melting point	−138.9 °C (−218.0 °F; 134.2 K) (cis); −105.5 °C (trans)
Boiling point	0.8 to 3.7 °C (33.4 to 38.7 °F; 273.9 to 276.8 K) (Z = 3.7 °C); (E = 0.8 °C)
Magnetic susceptibility (χ)	−42.6·10−6 cm3/mol (cis); −43.3·10−6 cm3/mol (trans);
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
NFPA 704 (fire diamond)	source ↗ 1 4 0
Flash point	−72 °C (−98 °F; 201 K)
Autoignition; temperature	325 °C (617 °F; 598 K)
Related compounds
Related butenes	1-Butene; cis-2-Butene; trans-2-Butene; Isobutene
Related compounds	Butane; Butyne
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

2-Butene is an acyclic alkene with four carbon atoms. It is the simplest alkene exhibiting cis/trans-isomerism (also known as (E/Z)-isomerism); that is, it exists as two geometric isomers cis-2-butene ((Z)-but-2-ene) and trans-2-butene ((E)-but-2-ene).

It is a petrochemical, produced by the catalytic cracking of crude oil or the dimerization of ethylene. Its main uses are in the production of high-octane gasoline (petrol) on alkylation units and butadiene,⁵ although some 2-butene is also used to produce the solvent butanone via hydration reaction to 2-butanol followed by oxidation.

The two isomers are extremely difficult to separate by distillation because of the proximity of their boiling points (~4 °C for cis and ~1 °C for trans⁶). However, separation is unnecessary in most industrial settings, as both isomers behave similarly in most of the desired reactions. A typical industrial 2-butene mixture is 70% (Z)-but-2-ene (cis-isomer) and 30% (E)-but-2-ene (trans-isomer). Butane and 1-butene are common impurities, present at 1% or more in industrial mixtures, which also contain smaller amounts of isobutene, butadiene and butyne.⁵

References

International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. P-45.6.2. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
cis-2-Butene, International Chemical Safety Card 0397, Geneva: International Programme on Chemical Safety, March 1996. trans-2-Butene, International Chemical Safety Card 0398, Geneva: International Programme on Chemical Safety, March 1996.
2-Butene (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
InChem: Chemical Safety Information from Intergovernmental Organizations Archived December 9, 2009, at the Wayback Machine

External links

SIDS Initial Assessment Report for 2-Butene from the Organisation for Economic Co-operation and Development (OECD)

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. P-45.6.2. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[GESTIScis-2] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[GESTIStrans-3] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[4] s-2-Butene, International Chemical Safety Card 0397, Geneva: International Programme on Chemical Safety, March 1996. trans-2-Butene, International Chemical Safety Card 0398, Geneva: International Programme on Chemical Safety, March 1996.

[SIDS-5] 2-Butene (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.

[6] InChem: Chemical Safety Information from Intergovernmental Organizations Archived December 9, 2009, at the Wayback Machine

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