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 
• 616-75-1 2-benzylmalonic acid 
• 3204-68-0 benzyldimethylphenylammonium chloride 
• 100-39-0 benzyl bromide 
• 82044-44-8 diethyl benzyl(prop-2'-en-1'-yl)propanedioate 
• 100-52-7 benzaldehyde 
• 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 
• 36861-61-7 3-benzyl-pyrido[1,2-a]pyrimidine-2,4-dione 
• 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 
• 859977-13-2 1,7-diphenyl-heptane-2,2,6,6-tetracarboxylic acid tetraethyl ester 
• 10444-15-2 diethyl 2-benzyl-2-(2-cyanoethyl)malonate 
• 15000-41-6 3-benzyl-quinoline-2,4-diol 
• 5243-31-2 An-mPhe-OH 
• 54505-60-1 4-benzyl-1-phenyl-3,5-pyrazolidinedione 
• 56640-46-1 1-(phenylmethyl)butanoic acid 
• 36092-42-9 2-benzylsuccinic acid 
• 128099-93-4 5-benzyl-6-hydroxy-1,2-dihydro-4H-pyrrolo<3,2,1-ij>quinolin-4-one 
• 90-47-1 xanth-9-one 
• 141221-74-1 2-Benzyl-2-(9H-xanthen-9-yl)-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.

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

FLP-catalysis meets hydrogen-bond activation

The potential of two chiral amidines and three non-chiral boranes in the metal-free hydrogen activation was explored. The resulting chiral amidiunium borohydride salts were investigated in asymmetric hydrogenation reactions of ketimines, activated double bonds and dehydro amioacid esters.