PIVALAMIDE Chemical Properties

Melting point:

154-157 °C (lit.)

Boiling point:

212 °C (lit.)

Density 

0.903±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.4380 (estimate)

Flash point:

212°C

storage temp. 

Sealed in dry,Room Temperature

pka

16.60±0.50(Predicted)

form 

Crystalline Powder

color 

White to very slightly yellow

BRN 

1742147

InChI

InChI=1S/C5H11NO/c1-5(2,3)4(6)7/h1-3H3,(H2,6,7)

InChIKey

XIPFMBOWZXULIA-UHFFFAOYSA-N

SMILES

C(N)(=O)C(C)(C)C

CAS DataBase Reference

754-10-9(CAS DataBase Reference)

EPA Substance Registry System

Propanamide, 2,2-dimethyl- (754-10-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

PIVALAMIDE Usage And Synthesis

Chemical Properties

WHITE TO VERY SLIGHTLY YELLOW CRYSTALLINE POWDER

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 4941, 1986 DOI: 10.1016/S0040-4039(00)85102-3

Synthesis

The general procedure for the synthesis of trimethylacetamide from pivalic acid is as follows: to a 10 mL THF colorless solution containing 75 mg (0.50 mmol) of 3-phenylpropionic acid 1a at 0 °C, 67 μL (0.70 mmol, 1.4 eq.) of ethyl chloroformate and 209 μL (1.5 mmol, 3.0 eq.) of triethylamine were added sequentially. The reaction mixture was stirred at 0 °C for 30 min before adding 0.75 mL of 1.0 M NH4Cl aqueous solution (0.75 mmol, 1.5 equiv). Stirring was continued at 0 °C for 30 min, followed by the addition of 5 mL of water. The reaction mixture was extracted with 30 mL of ethyl acetate and the aqueous layer was then extracted with 20 mL of ethyl acetate. The organic layers were combined, washed with 5 mL of brine and dried with anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate) to give 72 mg (96% yield) of 3-phenylpropionamide 2a. Synthesis of trimethylacetamide 2d: 44 mg (87% yield) of a colorless solid was obtained; melting point: 105-108 °C; 1H NMR (400 MHz, CDCl3): δ1.23 (s, 9H, CH3*3), δ1.21 (br, 1H, 1H). 5.21 (br, 1H, NHA), 5.59 (br, 1H, NHB); 13C NMR (100MHz, CDCl3): δ 27.7,38.7,181.6; IR (KBr, vmax/cm-1): 3398 (CONH), 3205 (CONH), 2960 (CH3), 1653 (CON), 1653 (CON). 1624 (CON); HRMS (ESI-TOF): calculated value C5H11NONa(M+Na)+: 124.0733, measured value: 124.0723.

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 315 - 318
[2] Chemistry Letters, 2008, vol. 37, # 12, p. 1191 - 1192
[3] Synthesis, 2003, # 2, p. 272 - 276
[4] Tetrahedron Asymmetry, 2017, vol. 28, # 12, p. 1690 - 1699
[5] Tetrahedron Letters, 2000, vol. 41, # 50, p. 9809 - 9813

PIVALAMIDE(754-10-9)Related Product Information

• Pivalic acid
• PYRITHYLDIONE
• Cytochalasin H
• PIVALAMIDE
• Aminoglutethimide
• oxyphenisatine di(acetate)
• 3,3-BIS(P-HYDROXYPHENYL)OXINDOLE
• 5-ethyldihydro-5-(2-methylallyl)-2-thioxo-1H,5H-pyrimidine-4,6-dione
• 2-Ethyl-2-phenylmalonamide
• 5,5-DIETHYLBARBITURIC ACID SODIUM SALT
• Phenobarbital sodium
• ALPHA-METHYL-ALPHA-PROPYLSUCCINIMIDE
• 5-ETHYL-5-P-TOLYLBARBITURIC ACID 99+%
• 4-HYDROXYPHENOBARBITAL
• N-(4-CHLORO-6-METHOXYPHENYL)-2,2-DIMETHYLPROPANAMIDE
• ALPHA,ALPHA-DIMETHYL-BETA-METHYLSUCCINIMIDE
• DIHYDRO-5-PHENYL-5-PROPYL-4,6(1H,5H)-PYRIMIDINEDIONE
• ALPHA-METHYL-ALPHA-PHENYLSUCCINIMIDE