609-02-9

Basic information

• Product Name: Dimethyl methylmalonate
• Synonyms: 2-methyl-malonicaciddimethylester;2-methyl-propanedioicaciddimethylester;Dimethyl 2-methylmalonate;Malonic acid, methyl-, dimethyl ester;methyl-propanedioicacidimethylester;Propanedioic acid, 2-methyl-, dimethyl ester;DIMETHYL METHYLMALONATE;Methylmalonicaciddimethylester
• CAS NO: 609-02-9
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 210-173-6
• Product Categories: Pharmaceutical Intermediates;C6 to C7;Carbonyl Compounds;Esters
• Mol File: 609-02-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 176-177 °C(lit.)
• Flash Point: 169 °F
• Appearance: /
• Density: 1.098 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.08±0.46(Predicted)
• CAS DataBase Reference: Dimethyl methylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl methylmalonate(609-02-9)
• EPA Substance Registry System: Dimethyl methylmalonate(609-02-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 609-02-9(Hazardous Substances Data)

Usage

General Description

Dimethyl methylmalonate is an ester. Microwave-enhanced Pd(0)/acetic acid catalyzed allylation of C, N and O-nucleophiles with dimethyl methylmalonate has been reported.

InChI:InChI=1/C7H8N4/c8-4-6-5-11-3-1-2-9-7(11)10-6/h1-3,5H,4,8H2

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 759-65-9 diethyl oxalpropionate 
• 39619-07-3 2-methylmalonyl dichloride 
• 116-11-0 2-Methoxypropene 
• 63921-06-2 3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 
• 108-59-8 malonic acid dimethyl ester 
• 50-00-0 formaldehyd 
• 74-88-4 methyl iodide 
• 292638-85-8 acrylic acid methyl ester 
• 80-62-6 methacrylic acid methyl ester 

Downstream Products

• 65896-61-9 2-methyl-2-n-propylpropanedioic acid dimethyl ester 
• 4165-96-2 3-phenylglutaric acid 
• 21118-89-8 2-<(4-methoxyphenyl)methyl>-2-methylpropanedioic acid, dimethyl ester 
• 81144-13-0 (3,4-Dioxo-2-phenylcyclobut-1-enyl)(methyl)malonsaeure-dimethylester 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 93-55-0 1-phenyl-propan-1-one 
• 204582-16-1 (4R,5R)-4-methyl-5-phenyl-1,3-dioxolan-2-one 
• 99-91-2 para-chloroacetophenone 
• 3609-53-8 methyl 4-acetylbenzoate 

Relevant articles and documents

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

“Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.