| Identification | Back Directory | [Name]
MONO-BENZYL MALONATE | [CAS]
40204-26-0 | [Synonyms]
MONO-BENZYL MALONATE
Mono-Benzyl Malonate 95%
MALONIC ACID MONO-BENZYL ESTER
3-oxo-3-phenylmethoxypropanoate
3-(benzyloxy)-3-oxopropanoic acid
3-oxo-3-phenylmethoxypropanoic acid
Propanedioic acid, 1-(phenylmethyl) ester
Propanedioic acid, Mono(phenylMethyl) ester | [Molecular Formula]
C10H10O4 | [MDL Number]
MFCD00138132 | [MOL File]
40204-26-0.mol | [Molecular Weight]
194.18 |
| Chemical Properties | Back Directory | [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) | [form ]
Powder or Crystalline Powder | [pka]
2.82±0.32(Predicted) | [color ]
White to off-white | [InChIKey]
CFLAHQSWDKNWPW-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [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 |
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