607-81-8

Basic information

• Product Name: Diethyl benzylmalonate
• Synonyms: BENZYLMALONIC ACID DIETHYL ESTER;DIETHYL BENZYLMALONATE;AKOS BBS-00006590;(phenylmethyl)-propanedioicacidiethylester;Diethyl 2-benzylmalonate;Malonic acid, 2-benzyl-, diethyl ester;Malonic acid, benzyl-, diethyl ester;Diethyl benzylmalonate,97%
• CAS NO: 607-81-8
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.29
• EINECS: 210-142-7
• Product Categories: Pharmaceutical Intermediates;Aromatic Esters;TheMalonateRamificationProducts;Aromatics Compounds;Aromatics;C12 to C63;Carbonyl Compounds;Esters;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 607-81-8.mol
• Article Data: 97

Chemical Properties

• Boiling Point: 162-163 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colourless Liquid
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• PKA: 12.56±0.46(Predicted)
• Water Solubility: immiscible
• BRN: 615793
• CAS DataBase Reference: Diethyl benzylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl benzylmalonate(607-81-8)
• EPA Substance Registry System: Diethyl benzylmalonate(607-81-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 607-81-8(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Liquid

Uses

Different sources of media describe the Uses of 607-81-8 differently. You can refer to the following data:
1. Diethyl Benzylmalonate (cas# 607-81-8) is a compound useful in organic synthesis.
2. Diethyl benzylmalonate was used in the synthesis of macrocyclic ligands and determination of stability constants of their Cu(II), Ni(II) and Co(II) complexes. It was used as starting reagent for the synthesis of 2-benzyl-1,3-propane diol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 620, 1966 DOI: 10.1021/jo01340a523

General Description

Diethyl benzylmalonate on condensation with 2-amino-benzimidazole yields 3-benzyl-4-hydroxypyrimido[1,2-a]benzimidazole-2-one.

InChI:InChI=1/C14H18O4/c1-3-17-13(15)12(14(16)18-4-2)10-11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3

Upstream product

• 996-82-7 sodium diethylmalonate 
• 3204-68-0 benzyldimethylphenylammonium chloride 
• 100-44-7 benzyl chloride 
• 105-53-3 diethyl malonate 
• 616-75-1 2-benzylmalonic acid 
• 55791-06-5 benzyl mesylate 
• 100-39-0 benzyl bromide 
• 92303-29-2 CH(CO₂C₂H₅)2 
• 103514-63-2 C₁₃H₂₅N₃PS⁽¹⁺⁾ 
• 82044-44-8 diethyl benzyl(prop-2'-en-1'-yl)propanedioate 
• 100-52-7 benzaldehyde 
• 123-91-1 1,4-dioxane 
• 854838-60-1 1,4-bis-(2,2-bis-ethoxycarbonyl-1-phenyl-ethyl)-piperazine 
• 60-29-7 diethyl ether 

Downstream Products

• 101599-89-7 4-benzyl-1-methyl-2-(1-methyl-[4]piperidyl)-pyrazolidine-3,5-dione 
• 75979-24-7 6-benzyl-2,3-dihydro-thiazolo[3,2-a]pyrimidine-5,7-dione 
• 101350-74-7 3-benzyl-1,2-dihydro-4-hydroxy-7-methyl-2-oxo-1,8-naphthyridine 
• 102162-95-8 benzyl-(2,6-dioxo-cyclohexylmethyl)-malonic acid dimethyl ester 
• 15018-53-8 5-benzyl-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 54986-54-8 2-butyl-3-hexyl-indene 
• 6943-96-0 ethyl 2-(hydroxyimino)-3-phenylpropanoate 
• 107524-40-3 benzyl-(2-methylsulfanyl-ethyl)-malonic acid diethyl ester 
• 116055-59-5 5-benzyl-2-seleno-barbituric acid 
• 23450-66-0 5-benzyl-1-methyl-barbituric acid 
• 101499-51-8 2-benzyl-octanedioic acid 
• 103034-83-9 2-benzyl-tridecanedioic acid diethyl ester 
• 361446-66-4 5-benzyl-1-phenyl-barbituric acid 
• 859200-53-6 benzyl-(3-bromo-benzyl)-malonic acid diethyl ester 

Relevant articles and documents

Solid Molecular Frustrated Lewis Pairs in a Polyamine Organic Framework for the Catalytic Metal-free Hydrogenation of Alkenes

We report for the first time a metal-free heterogeneously catalyzed hydrogenation using a semi-solid frustrated Lewis pair (FLP). The catalyst consists of a solid polyamine organic framework and molecular tris(pentafluorophenyl)borane (BCF) that form a semi-immobilized FLP in situ in the catalytic hydrogenation of diethyl benzylidenemalonate. 11B NMR spectroscopy proves the successful hydrogen activation by the FLP. Furthermore, the B?N interactions between the polyamine and BCF are investigated by IR and solid state NMR spectroscopy. The FLP 1,4-diazabicyclo[2.2.2]octane (DABCO)/BCF, which combines the features of a FLP and a classical Lewis adduct, functions as molecular reference in both, catalysis and characterization. Furthermore, computational studies enable a better insight into the hydrogen activation through DABCO/BCF and polyamine/BCF.

FRUSTRATED LEWIS PAIR-IMPREGNATED POROUS MATERIALS AND USES THEREOF

Described herein are compositions composed of frustrated Lewis pairs impregnated in porous materials such as, for example, metal-organic frameworks, and their uses thereof. These compositions may allow new applications of frustrated Lewis pairs in catalysis by sequestering and protecting the frustrated Lewis pair within the nanospace of the porous material. Also provided are methods of hydrogenating an organic compound having at least one unsaturated functional group comprising using the compositions described herein.

Validating the 1,2-Difluoro Motif As a Hybrid Bioisostere of CF3and et Using Matrix Metalloproteinases As Structural Probes

Matrix metalloproteinases (MMPs) are involved in a spectrum of physiological processes, rendering them attractive targets for small-molecule drug discovery. Strategies to achieve selective inhibition continue to be intensively pursued, facilitated by advances in structural biology. Herein, we harness MMPs 2, 8, 9, and 13 to validate the vicinal difluoro motif as a hybrid bioisostere of CF3 and Et (BITE) in a series of modified barbiturate inhibitors. Crystallographic analyses of representative structures reveal conformations of the vicinal difluoro motif that manifest stabilizing hyperconjugative interactions consistent with the stereoelectronic gauche effect. Detailed docking studies of a potent difluorinated probe with MMP-9 are also disclosed and indicate that the structural basis of inhibition is a consequence of the anisotropic nature of the motif. Significant selectivity of MMP 13 versus MMP-2 can be achieved by subtle chain contraction in a BITE-modified inhibitor.