Pivaloylacetonitrile Chemical Properties

Melting point:

66-69 °C(lit.)

Boiling point:

125-126 °C22 mm Hg(lit.)

Density 

1.0459 (rough estimate)

refractive index 

1.4693 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.25±0.10(Predicted)

form 

Crystals or Crystalline Powder

color 

White to cream

Water Solubility 

Insoluble in water.

BRN 

1746674

InChI

InChI=1S/C7H11NO/c1-7(2,3)6(9)4-5-8/h4H2,1-3H3

InChIKey

MXZMACXOMZKYHJ-UHFFFAOYSA-N

SMILES

C(#N)CC(=O)C(C)(C)C

CAS DataBase Reference

59997-51-2(CAS DataBase Reference)

NIST Chemistry Reference

4,4-Dimethyl-3-oxopentanenitrile(59997-51-2)

EPA Substance Registry System

Pentanenitrile, 4,4-dimethyl-3-oxo- (59997-51-2)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

36/37/39-45

RIDADR 

UN 3439 6.1/PG 3

WGK Germany 

3

RTECS 

SA2991000

F 

8

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:4,4-Dimethyl-3-oxovaleronitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pivaloylacetonitrile Usage And Synthesis

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

Pivaloylacetonitrile(59997-51-2)Related Product Information

• Methylene dithiocyanate
• Dimethyl sulfide
• Dimethyl sebacate
• Iminodiacetonitrile
• 2-Chloro-3-cyanopyridine
• N,N-Dimethylformamide
• Dimethyl sulfoxide
• Dimethyl sulfate
• Dimethyl fumarate
• Dimethyl carbonate
• Dimethyl ether
• Cyanoacetic acid
• Dacthal
• Ethyl N-cyanoethanimideate
• ETHANE
• Sodium cyanoborohydride
• ETHYL 2-CYANOACRYLATE
• Methyl pivaloylacetate