PIVALOYL CYANIDE

The 3,3-Dimethyl-2-oxobutanenitrile, with the CAS registry number 42867-40-3, is also known as Pivaloyl cyanide. Its EINECS registry number is 255-978-3. This chemical's molecular formula is C₆H₉NO and molecular weight is 111.14. What's more, both its IUPAC name and systematic name are the same which is called 3,3-Dimethyl-2-oxobutanenitrile.

Physical properties about 3,3-Dimethyl-2-oxobutanenitrile are: (1)ACD/LogP: 1.227; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.23; (4)ACD/LogD (pH 7.4): 1.23; (5)ACD/BCF (pH 5.5): 5.04; (6)ACD/BCF (pH 7.4): 5.04; (7)ACD/KOC (pH 5.5): 110.80; (8)ACD/KOC (pH 7.4): 110.80; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 40.86 Å²; (13)Index of Refraction: 1.418; (14)Molar Refractivity: 29.755 cm³; (15)Molar Volume: 118.127 cm³; (16)Polarizability: 11.796×10^-24cm³; (17)Surface Tension: 31.26 dyne/cm; (18)Density: 0.941 g/cm³; (19)Flash Point: 42.504 °C; (20)Enthalpy of Vaporization: 38.367 kJ/mol; (21)Boiling Point: 146.669 °C at 760 mmHg ; (22)Vapour Pressure: 4.587 mmHg at 25 °C.

Preparation of 3,3-Dimethyl-2-oxobutanenitrile: this chemical can be prepared by 2,2-dimethyl-propionyl chloride with tributyltin cyanide. This reaction temperature is 30 °C and reaction time is 10 min. The yield is 92.2 %.

Uses of 3,3-Dimethyl-2-oxobutanenitrile: it is used to produce other chemicals. For example, it can react with N-(4-chloro-phenyl)-hydroxylamine to get N-(4-chlorophenyl)-O-pivaloylhydroxylamine. The reaction needs reagent N-ethylmorpholine and solvent at ambient temperature.

The reaction time is 20 min. The yield is 75 %.You can still convert the following datas into molecular structure:
(1) SMILES: N#CC(=O)C(C)(C)C
(2) InChI: InChI=1S/C6H9NO/c1-6(2,3)5(8)4-7/h1-3H3
(3) InChIKey: NPBLQPWAISGYEU-UHFFFAOYSA-N