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

Description

Diethyl benzylmalonate, with the chemical formula C17H20O4, is a colorless liquid that is widely utilized in the field of organic synthesis. It is known for its ability to form macrocyclic ligands and complexes with various metal ions, such as Cu(II), Ni(II), and Co(II). This versatile compound is also used as a starting reagent for the synthesis of 2-benzyl-1,3-propane diol and undergoes condensation with 2-amino-benzimidazole to yield 3-benzyl-4-hydroxypyrimido[1,2-a]benzimidazole-2-one.

Uses

1. Used in Organic Synthesis:
Diethyl benzylmalonate is used as a key intermediate in the synthesis of various organic compounds. Its ability to form complexes with metal ions makes it a valuable component in the development of new chemical structures and materials.
2. Used in the Synthesis of Macrocyclic Ligands:
Diethyl benzylmalonate is employed as a starting reagent for the synthesis of macrocyclic ligands, which are essential in the formation of stability constants with Cu(II), Ni(II), and Co(II) complexes. These complexes have potential applications in various fields, including catalysis and coordination chemistry.
3. Used in the Synthesis of 2-Benzyl-1,3-Propane Diol:
As a starting reagent, Diethyl benzylmalonate is used in the synthesis of 2-benzyl-1,3-propane diol, a compound with potential applications in the pharmaceutical and chemical industries.
4. Used in the Condensation with 2-Amino-Benzimidazole:
Diethyl benzylmalonate is used in the condensation reaction with 2-amino-benzimidazole, resulting in the formation of 3-benzyl-4-hydroxypyrimido[1,2-a]benzimidazole-2-one. Diethyl benzylmalonate may have potential applications in the development of new drugs and pharmaceuticals.

Synthesis Reference(s)

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

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 
• 100-44-7 benzyl chloride 
• 996-82-7 sodium diethylmalonate 
• 105-53-3 diethyl malonate 
• 2021-28-5 ethyl dihydrocinnamate 
• 141-52-6 sodium ethanolate 
• 105-58-8 Diethyl carbonate 
• 55791-06-5 benzyl mesylate 
• 100-51-6 benzyl alcohol 
• 60-29-7 diethyl ether 
• 5292-53-5 diethyl benzalmalonate 
• 7664-41-7 ammonia 
• 85533-87-5 4-phenyl-but-1-ene-1,1,3,3-tetracarboxylic acid tetraethyl ester 
• 100-63-0 phenylhydrazine 

Downstream Products

• 101268-99-9 4-benzyl-1-(1-methyl-[4]piperidyl)-pyrazolidine-3,5-dione 
• 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 
• 36861-61-7 3-benzyl-pyrido[1,2-a]pyrimidine-2,4-dione 
• 101350-74-7 3-benzyl-1,2-dihydro-4-hydroxy-7-methyl-2-oxo-1,8-naphthyridine 
• 412337-51-0 2-benzyl-1-hydroxy-4H-[4,7]phenanthrolin-3-one 
• 109554-51-0 3-phenyl-1,2,2-propanetricarboxylic acid 1,2,2-triethyl ester 
• 502769-47-3 2-benzyl-2-[3-(dimethylamino)propyl] malonic acid diethyl ester 
• 120537-84-0 7-amino-3-benzyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine 
• 114469-28-2 2-Benzyl-2-(3,3-dimethyl-2-oxo-butyl)-malonic acid diethyl ester 
• 129082-04-8 diethyl benzyl(4-phenylbut-2-enyl)malonate 
• 141344-93-6 2,2-Bis(ethoxycarbonyl)-4-phenyl-1,2-dihydronaphthalene 
• 160618-33-7 6-benzyl-1,4,8,11-tetraazaundecane-5,7-dione 
• 5292-53-5 diethyl benzalmalonate 

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.