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DIBENZYL MALONATE

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DIBENZYL MALONATE Basic information

Product Name:
DIBENZYL MALONATE
Synonyms:
  • Propanedioic acid, bis(phenylmethyl) ester
  • Dibenzyl malonate, tech., 90%
  • propanedioic acid dibenzyl ester
  • MALONIC ACID DIBENZYL ESTER
  • 2,5-Dimethyl-3-Hezine-Diol
  • Dibenzylmalonateca
  • Malonic acid dibenzyl ester~Propanedioic acid dibenzyl ester
  • DIBENZYL MALONATE
CAS:
15014-25-2
MF:
C17H16O4
MW:
284.31
EINECS:
239-099-2
Product Categories:
  • Building Blocks
  • C12 to C63
  • C12 to C63
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • Carbonyl Compounds
  • Esters
Mol File:
15014-25-2.mol
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DIBENZYL MALONATE Chemical Properties

Boiling point:
188 °C/0.2 mmHg (lit.)
Density 
1.137 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.546(lit.)
Flash point:
>230 °F
storage temp. 
Sealed in dry,Room Temperature
pka
11.65±0.46(Predicted)
form 
clear liquid
color 
Colorless to Light yellow to Light orange
Specific Gravity
1.17
Water Solubility 
Sparingly soluble in water; miscible in all proportions with ether and alcohol.
BRN 
1998264
InChIKey
RYFCSKVXWRJEOB-UHFFFAOYSA-N
CAS DataBase Reference
15014-25-2(CAS DataBase Reference)
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Safety Information

Safety Statements 
23-24/25
WGK Germany 
3
HS Code 
29171910

MSDS

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DIBENZYL MALONATE Usage And Synthesis

Chemical Properties

CLEAR YELLOWISH LIQUID

Uses

Dibenzyl malonate was used in the preparation of tetraethyl 3,3-bis(benzyloxycarbonyl)propylene bisphosphonate. It was also used in the preparation of benzyl umbelliferone-3-carboxylate via Knoevenagel condensation with 2,4-dihydroxybezaldehyde.

General Description

Direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox (pybox = pyridine bisoxazoline) complexes has been investigated.

Purification Methods

Dissolve the ester in toluene, wash it with aqueous NaHCO3, H2O, dry over MgSO4, filter, evaporate and distil it at high vacuum. [Ginsburg & Pappo J Am Chem Soc 75 1094 1953, Baker et al. J Org Chem 17 77 1952, Beilstein 6 IV 2270.]

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