3-Penten-2-one

3-Penten-2-one
Names
	Preferred IUPAC name Pent-3-en-2-one
	Other names Ethylidene acetone
Identifiers
CAS Number	625-33-2 (unspecified) ; 3102-33-8 (E) ; 3102-32-7 (Z) ;
3D model (JSmol)	(E): Interactive image; (Z): Interactive image;
Beilstein Reference	3-01-00-02985
ChemSpider	11747 (unspecified); 553493 (E); 4512214 (Z);
ECHA InfoCard	100.009.899
EC Number	210-888-3;
PubChem CID	12248 (unspecified); 637920 (E); 5356572 (Z);
UNII	4WN5NGB7KX (E) ; W8XX21WHYC (Z) ;
CompTox Dashboard (EPA)	DTXSID0060800 ;
	InChI (unspecified): InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3 Key: LABTWGUMFABVFG-UHFFFAOYSA-N; (E): InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+ Key: LABTWGUMFABVFG-ONEGZZNKSA-N; (Z): InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3- Key: LABTWGUMFABVFG-ARJAWSKDSA-N;
	SMILES (unspecified): CC=CC(=O)C; (E): C/C=C/C(=O)C; (Z): C/C=C\C(=O)C;
Properties
Chemical formula	C5H8O
Molar mass	84.118 g·mol−1
Appearance	colourless liquid
Density	0.861 g·cm−3; 0,862 g·cm−3 (E)
Boiling point	122 °C (252 °F; 395 K)
Solubility in water	soluble in water, acetone and ether (E)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable and toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H312, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS)	Safety Data Sheet
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Penten-2-one is an organic compound with the formula CH₃C(O)CH=CHCH₃. It exists as (E) and (Z) stereoisomers. The compound is classified as an α,β-unsaturated ketone. It is a colorless volatile liquid with fruity to pungent odor.^[4]^[5]

Preparation, occurrence, uses

The (E) isomer is classically obtained from the 3-chloropentanone by dehydrohalogenation.^[6] It can also be obtained by dehydration of 4-hydroxy-pentan-2-one using oxalic acid as a catalyst.^[5]

3-Penten-2-one occurs naturally in the berries of two species of Aronia melanocarpa.^[7] It has also been found in other plants and foods such as tomatoes, cocoa, tea, and potato chips.^[5]

3-Penten-2-one can be used for the synthesis of other compounds such as the alkaloids senepodine G and cermizine C, for example.^[7] It is also a useful flavoring agent.^[5]

References

^ ^a ^b Record of 3-Penten-2-on in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 25 July 2017.
^ Carl L. Yaws (2015), The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics, Gulf Professional Publishing, p. 72, ISBN 978-0-12-801146-1
^ William M. Haynes (2016), CRC Handbook of Chemistry and Physics (97th ed.), CRC Press, p. 440, ISBN 978-1-4987-5429-3
^ "L13031 3-Penten-2-one, tech. 85%". Alfa Aesar.
^ ^a ^b ^c ^d George A. Burdock (1997), Encyclopedia of Food and Color Additives, CRC Press, p. 2997, ISBN 978-0-8493-9414-0
^ H. C. Odom & A. R. Pinder (1971). "trans-3-Penten-2-one". Org. Synth. 51: 115. doi:10.15227/orgsyn.051.0115.
^ ^a ^b Sigma-Aldrich Co., product no. {{{id}}}.

[GESTIS-1] Record of 3-Penten-2-on in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 25 July 2017.

[Carl_L._Yaws-2] Carl L. Yaws (2015), The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics, Gulf Professional Publishing, p. 72, ISBN 978-0-12-801146-1

[William_M._Haynes-3] William M. Haynes (2016), CRC Handbook of Chemistry and Physics (97th ed.), CRC Press, p. 440, ISBN 978-1-4987-5429-3

[Alfa-4] "L13031 3-Penten-2-one, tech. 85%". Alfa Aesar.

[George_A._Burdock-5] George A. Burdock (1997), Encyclopedia of Food and Color Additives, CRC Press, p. 2997, ISBN 978-0-8493-9414-0

[6] H. C. Odom & A. R. Pinder (1971). "trans-3-Penten-2-one". Org. Synth. 51: 115. doi:10.15227/orgsyn.051.0115.

[Sigma-7] Sigma-Aldrich Co., product no. {{{id}}}.

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