2-Undecanone
| Names | |
|---|---|
| Preferred IUPAC name
Undecan-2-one | |
| Other names
Methyl nonyl ketone (MNK)
Nonyl methyl ketone Methyldecananone 2-Hendecanone Undecanone IBI-246 | |
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| Properties | |
| C11H22O | |
| Molar mass | 170.296 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.829 g/cm3, liquid |
| Melting point | 15 °C (59 °F; 288 K) |
| Boiling point | 231 °C (448 °F; 504 K) |
| 0.00179 g/100 mL (25 °C) | |
| Hazards | |
| GHS labelling: | |
| GHS09: Environmental hazard | |
| Warning | |
| H400 | |
| P273, P391, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 88 °C (190 °F; 361 K) |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related Ketones
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Acetone Butan-2-one 3-pentanone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an organic compound with the formula CH3C(O)C9H19. It is a colorless oil. 2-Undecanone is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial leaf vegetable Houttuynia cordata.[1]
Uses
[edit | edit source]Because of its strong odor it is primarily used as an insect repellent or animal repellent. 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 also used in the perfumery and flavoring industries.
It has been investigated as a mosquito repellant, like DEET.[2][3]
Chemical properties
[edit | edit source]2-Undecanone is a ketone that is soluble in organic solvents but insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.
- CH3CO(CH2)8CH3 + 3 NaOCl → CH3(CH2)8COONa + CHCl3 + 2 NaOH
See also
[edit | edit source]Notes
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET Archived 2023-09-28 at the Wayback Machine, Science Daily, June 2002
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
References
[edit | edit source]- Lange's Handbook of Chemistry (14th Edition), McGraw-Hill, 1992; Section 1; Table 1.15
- The Condensed Chemical Dictionary (10th Edition), Gesner G. Hawley
- 2-Undecanone from The Good Scents Company
- MSDS for 2-Undecanone[permanent dead link]