MONO-BENZYL MALONATE Chemical Properties

Melting point:

47-51 °C (lit.)

Boiling point:

352.3±25.0 °C(Predicted)

Density 

1.0737 g/cm3

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

2.82±0.32(Predicted)

form 

Powder or Crystalline Powder

color 

White to off-white

InChIKey

CFLAHQSWDKNWPW-UHFFFAOYSA-N

Safety Information

WGK Germany 

3

HS Code 

2917399590

MONO-BENZYL MALONATE Usage And Synthesis

Uses

Monobenzyl Malonate is a useful synthetic intermediate. It was used to synthesize constrained cyclic agonists of the cholecystokinin CCK-B receptor. It was also used to prepare aspartate transcarbamoylase inhibitors.

Definition

ChEBI: A dicarboxylic acid monoester obtained by the formal condensation of one of the carboxy groups of malonic acid with benzyl alcohol.

General Description

mono-Benzyl malonate can be synthesized by the reaction of Meldrum′s acid (2,2-dimethyl- 1,3-dioxane-4,6-dione) with benzyl alcohol.

Synthesis

Meldrum acid (2.00 g, 13.8 mmol) and anhydrous acetonitrile (40 mL) were added to a flame-dried 150 mL pressure tube under argon protection. Benzyl alcohol (1.44 mL, 13.8 mmol) was added to the resulting solution and the reaction tube was sealed. The reaction mixture was refluxed overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the product was purified by column chromatography (eluent: 70/30 hexane/ethyl acetate) to afford the target product, monophenylmethyl malonate (1.28 g, 6.59 mmol), as a colorless oil in 48% yield.

References

[1] Helvetica Chimica Acta, 2002, vol. 85, # 1, p. 288 - 319
[2] Heterocycles, 1993, vol. 35, # 2, p. 1205 - 1235
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1143 - 1148
[4] Journal of Organometallic Chemistry, 2001, vol. 619, # 1-2, p. 179 - 193
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 21, p. 4933 - 4936

MONO-BENZYL MALONATE(40204-26-0)Related Product Information

• BENZYL TERT-BUTYL MALONATE
• BENZYL ETHYL MALONATE
• PHENYLMALONIC ACID MONOBENZYL ESTER
• MONO-BENZYL MALONATE
• MALONIC ACID MONO-4-NITROBENZYL ESTER MAGNESIUM SALT
• Anhydrous Magnesium Mono-Benzyl Malonate
• 4-Nitrobenzyl hydrogen malonate
• BENZYL METHYL MALONATE
• DIBENZYL MALONATE
• Malonic acid
• MALONIC ACID BIS(4-NITROBENZYL) ESTER
• MONO-BENZYL MALONATE
• FMOC-DL-GLA(OBZL)2-OH
• BOC-DL-GLA(OBZL)2-OH
• 5-METHYL-2-OXO-5-PHENYL-2,5-DIHYDROFURAN-3-CARBOXYLIC ACID METHYL ESTER
• BOC-L-GLA(OBZL)2-OH
• FMOC-L-GLA(OBZL)2-OH
• 2,5-DIHYDRO-2-OXO-5-PHENYL-5-(2-PROPENYL)-3-FURANCARBOXYLIC ACID, METHYL ESTER