| Identification | More | [Name]
Pivaloylacetonitrile | [CAS]
59997-51-2 | [Synonyms]
1-CYANO-3,3-DIMETHYL-2-BUTANONE
4,4-DIMETHYL-3-OXO-N-VALERONITRILE
4,4-DIMETHYL-3-OXOPENTANENITRILE
4,4-dimethyl-3-oxovaleronitrile
CYANOPINACOLONE
PIVALOYLACETONITRILE
TIMTEC-BB SBB008437
TRIMETHYLACETYLACETONITRILE
4,4-dimethyl-3-oxo-pentanenitril
Pentanenitrile, 4,4-dimethyl-3-oxo-
1-Cyanopinacolone
Pivaloyl Acetonitrile 99%min
4,4-DIMETHYL-3-OXOVALERONITRILE(PIVALOYLACETONITRILE)
4,4,-Dimethyl-3-Ox-Valeronitrile(Pivaloylacetonitrile)
Trimethylacetylacetonitrile, 98+%
Trimethylacetylacetonitrile,99%
4,4-DIMETHYL-3-OXOPENTANENITRILE(PIVALOYLACETONITRILE)
PIVALOYLACETONITRILE (4,4-DIMETHYL-3-OXOPENTANENITRILE) (1-CYANOPINACOLONE)
Valeronitrile, 4,4-dimethyl-3-oxo
3-Oxo-4,4-dimethylpentanenitrile | [EINECS(EC#)]
262-017-1 | [Molecular Formula]
C7H11NO | [MDL Number]
MFCD00010208 | [Molecular Weight]
125.17 | [MOL File]
59997-51-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3439 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
SA2991000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to cream crystals or crystalline powder | [Uses]
Trimethylacetylacetonitrile is a useful intermediate. 4,4-Dimethyl-3-oxopentanenitrile has been used in the preparation of 4,4-dimethyl-3-oxo-2-benzylpentanenitrile, 4,4-dimethyl-3-oxo-2-(4-hydroxybenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(4-methoxybenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(4-fluorobenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(3,4-methylenedioxybenzyl)pentanenitrile, 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-phenylurea. | [Synthesis]
1. NaH (50% in paraffin oil, 1.2 eq., 4.6 g) was added to 1,4-dioxane (120 ml) and stirred for several minutes to disperse the mixture.
2. Acetonitrile (1.2 eq., 4.2 g) was slowly added dropwise to the above mixture over a period of 15 minutes and stirring was continued for 30 minutes after completion of the addition.
3. Methyl pivalate (1 eq., 10 g) was added slowly and dropwise to the reaction system over 15 minutes, after which the reaction mixture was heated to reflux for 3 hours.
4. After completion of the reaction, the reaction mixture was poured into ice water (200 g) and the pH was adjusted to 4.5 with acid.
5. The aqueous phase was extracted several times with dichloromethane (12 x 250 ml) and the organic phase was combined.
6. The combined organic phases were dried with anhydrous sodium sulfate, filtered and concentrated.
7. The concentrate was recrystallized with hexane (100 ml) to give the brown solid product 4,4-dimethyl-3-oxopentanenitrile (5 g, 51% yield). | [References]
[1] Tetrahedron, 1993, vol. 49, # 23, p. 5091 - 5098
[2] Journal of the Chemical Society, Chemical Communications, 1992, # 1, p. 50 - 51
[3] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 95
[4] Patent: WO2010/127856, 2010, A1. Location in patent: Page/Page column 78
[5] Patent: US2012/46301, 2012, A1. Location in patent: Page/Page column 28; 29 |
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