TERT-BUTYL METHYL MALONATE Chemical Properties

Melting point:

-10 °C

Boiling point:

80 °C11 mm Hg(lit.)

Density 

1.03 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.415(lit.)

Flash point:

175 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

11.83±0.46(Predicted)

form 

Liquid

color 

Clear colorless to slightly yellow

BRN 

1772136

InChI

InChI=1S/C8H14O4/c1-8(2,3)12-7(10)5-6(9)11-4/h5H2,1-4H3

InChIKey

XPSYZCWYRWHVCC-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CC(OC)=O

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

29171900

MSDS

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

TERT-BUTYL METHYL MALONATE Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

General Description

tert-Butyl methyl malonate is an ester. Stereospecific Pd(O)-catalyzed addition of tert-butyl methyl malonate to allylic carbonates is reported.

Synthesis

To a 200 mL round bottom flask equipped with a magnetic stirrer was added mono-tert-butyl malonate (3.0 g, 18.7 mmol) and methanol (70 mL). To this solution was added hafnium(IV) chloride tetrahydrofuran complex (1:2) (88 mg, 0.19 mmol). The reaction mixture was stirred at room temperature for 48 hours. After completion of the reaction, saturated saline was added to the mixture and extracted with dichloromethane (3 x 70 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 50:50) to afford the target compound tert-butyl methyl malonate (3.0 g, 91% yield) as a colorless oily liquid.1H NMR (400 MHz, CDCl3) δ 3.74 (s, 3H), 3.30 (s, 2H), 1.47 (s, 9H); 13C NMR ( 100 MHz, CDCl3) δ 167.5, 165.8, 82.1, 52.3, 42.7, 27.9; HR-FAB MS m/z calculated value C8H15O4 [M+H]+ 175.0883, measured value 175.0875.

References

[1] Tetrahedron Asymmetry, 2015, vol. 26, # 4, p. 214 - 218

TERT-BUTYL METHYL MALONATE(42726-73-8)Related Product Information

• BENZYL TERT-BUTYL MALONATE
• Di-tert-Butyl malonate
• TERT-BUTYL ETHYL MALONATE
• Diisopropyl malonate
• Ethyl potassium malonate
• 3-tert-Butoxy-3-oxopropanoic acid
• Dimethyl malonate
• Potassium 3-methoxy-3-oxopropanoate
• Ethyl hydrogen malonate
• Diethyl malonate
• MONOMETHYL MALONATE
• Malonic acid
• tert-Butylhydrazine hydrochloride
• tert-Butyldimethylsilyl chloride
• tert-butyl((4-bromo-5-cyano-1-methyl-1H-pyrazol-3-yl)methyl)(methyl)carbamate
• tert-Butyl nitrite
• tert-Butylchlorodiphenylsilane
• Coumarin 338