2-Undecanone
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2008-05-04T20:02:57Z
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{{Chembox new
| Name = 2-Undecanone
| ImageFile = 2-undecanone.svg
<!-- | ImageSize = 300px -->
| ImageName = 2-undecanone
| OtherNames = Methyl nonyl ketone (MNK)</br>Nonyl methyl ketone</br>Methyldecananone</br>2-Hendecanone</br>Undecanone
| Section1 = {{Chembox Identifiers
| SMILES = CCCCCCCCCC(=O)C
| CASNo = 112-12-9
| RTECS = YQ2820000
}}
| Section2 = {{Chembox Properties
| Formula = CH<sub>3</sub>CO(CH<sub>2</sub>)<sub>8</sub>CH<sub>3</sub>
| MolarMass = 170.2942 g/mol
| Appearance = Colorless or pale yellow liquid
| Density = 0.829 g/cm³, liquid
| Solubility = 0.00179 g/100 ml (25 °C)
| MeltingPt = 15 °C (288 K)
| BoilingPt = 231 °C (504 K)
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/UN/2-undecanone.html External MSDS]
| EUClass = Flammable ('''F''')<br />Irritant ('''Xi''')
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R =
| RPhrases = {{R50}}, {{R51}}
| SPhrases = {{S23}}, {{S24}}, {{S25}}
| FlashPt = 88 °C
}}
| Section8 = {{Chembox Related
| Function = [[Ketone]]s
| OtherFunctn = [[Acetone]]<br />[[Butanone|Butan-2-one]]</br>[[3-Pentanone|3-pentanone]]
}}
}}
'''2-Undecanone''' is an oily [[organic chemistry|organic]] liquid manufactured synthetically, but which can also be extracted from oil of [[rue]]. It is found naturally in bananas, cloves, ginger, guava, and strawberries. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect or animal repellant. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, [[aerosol spray]], or gel.
2-Undecanone is a [[ketone]], also known as '''methyl nonyl ketone (MNK)'''. It is soluble in [[ethanol]], [[benzene]], [[chloroform]], and [[acetone]], but its large carbon chain renders it insoluble in water. Like most [[methyl]] [[ketone]]s, 2-undecanone undergoes a [[haloform reaction]] when in the presence of a base. For example, the reaction between 2-undecanone and [[sodium hypochlorite]] yields [[sodium decanoate]], [[chloroform]], and [[sodium hydroxide]].
CH<sub>3</sub>CO(CH<sub>2</sub>)<sub>8</sub>CH<sub>3</sub> + 3NaOCl → CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COONa + CHCl<sub>3</sub> + 2NaOH
==References==
* ''Lange's Handbook of Chemistry (14th Edition)'', McGraw-Hill, 1992; Section 1; Table 1.15
* ''The Condensed Chemical Dictionary (10th Edition)'', Gesner G. Hawley
* http://www.thegoodscentscompany.com/data/rw1021151.html
<references/>{{citationstyle}}
[[Category:Ketones|Undecanone, 2-]]