78606-96-9

Basic information

• Product Name: 2-(2-METHYLBENZYL)-MALONIC ACID
• Synonyms: 2-(2-METHYLBENZYL)-MALONIC ACID;RARECHEM DK HC T303;2-(2-Methoxybenzyl)malonic acid
• CAS NO: 78606-96-9
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• Mol File: 78606-96-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 393 °C at 760 mmHg
• Flash Point: 205.6 °C
• Appearance: /
• Density: 1.291 g/cm³
• Vapor Pressure: 7E-07mmHg at 25°C
• Refractive Index: 1.571
• PKA: 3.22±0.11(Predicted)
• CAS DataBase Reference: 2-(2-METHYLBENZYL)-MALONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHYLBENZYL)-MALONIC ACID(78606-96-9)
• EPA Substance Registry System: 2-(2-METHYLBENZYL)-MALONIC ACID(78606-96-9)

Safety Data

• Hazardous Substances Data: 78606-96-9(Hazardous Substances Data)

Usage

Description

2-(2-METHYLBENZYL)-MALONIC ACID is a chemical compound characterized by the molecular formula C12H12O4. It is a derivative of malonic acid, featuring a methylbenzyl group attached to its structure. This unique arrangement endows it with potential applications in organic synthesis and pharmaceutical research, where it serves as a versatile building block for the creation of complex organic molecules.

Uses

Used in Organic Synthesis:
2-(2-METHYLBENZYL)-MALONIC ACID is used as a key intermediate in the synthesis of various organic compounds due to its distinctive structure. It plays a crucial role in the formation of complex organic molecules, which can have a wide range of applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(2-METHYLBENZYL)-MALONIC ACID is utilized as a building block for the development of pharmaceutical drugs. Its unique structure allows for the creation of new drug candidates that can address specific medical needs.
Used in Agrochemical Development:
2-(2-METHYLBENZYL)-MALONIC ACID also finds application in the agrochemical sector, where it is used as a starting material for the synthesis of agrochemicals. Its versatility enables the development of new compounds that can improve crop protection and yield.
As an Important Reagent in Organic Chemistry:
2-(2-METHYLBENZYL)-MALONIC ACID is recognized as an important reagent in the field of organic chemistry. Its role as a versatile intermediate makes it instrumental in the synthesis of a variety of organic compounds, contributing to the advancement of chemical research and development.

InChI:InChI=1/C11H12O4/c1-7-4-2-3-5-8(7)6-9(10(12)13)11(14)15/h2-5,9H,6H2,1H3,(H,12,13)(H,14,15)

Upstream product

• 89-92-9 2-methylbenzyl bromide 
• 105-53-3 diethyl malonate 
• 58818-65-8 o-methylphenylmethylenemalonic acid 
• 6619-57-4 diethyl 2-(2-methylbenzyl)-malonate 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 22084-89-5 3-(2-methylphenyl)propanoic acid 
• 24644-78-8 4-methylindanone 
• 85829-29-4 3-(2-methylphenyl)propionic acid chloride 
• 192987-46-5 4-[1-(1-hydroxy-4-methylindanyl)]-N-(triphenylmethyl)imidazole 

Relevant articles and documents

Medetomidine analogs as α2-adrenergic ligands. 3. Synthesis and biological evaluation of a new series of medetomidine analogs and their potential binding interactions with α2-adrenoceptors involving a 'methyl pocket'

The synthesis and the biological evaluation of a new series of medetomidine analogs are reported. The substitution pattern at the phenyl ring of the tetralin analogs had a distinct influence on the α2- adrenoceptor binding affinity. 4-Methylindan analog 6 was the most potent α2-adrenoceptor binding ligand among these 4-substituted imidazoles, and its α2-adrenoceptor selectivity was greater than the 5-methyl tetralin analog 4c. Ligand-pharmacophore and receptor modeling were combined to rationalize α2-adrenoceptor binding data of the imidazole analogs in terms of ligand-receptor interactions. The structure-activity relationships that were apparent from this and previous studies were qualitatively rationalized by the binding site models of the α2-adrenoceptor. The benzylic methyl group of medetomidine or the naphthyl analog 2a was superimposable with the α-methyl group of (-)-α-methylnorepinephrine and fit into the proposed 'methyl pocket' of the α2-adrenoceptor defined by the residues Leu110, Leu169, Phe391, and Thr395.

Synthesis of Polycyclic Aromatic Hydrocarbons via a Novel Annelation Method

A new general synthetic approach to polycyclic aromatic hydrocarbons is described.The method is based on the convenient availability of o-lithioarylamides from regiospecific metalation of N,N-diethylarylamides with alkyllithium-amine reagents.Addition of the o-lithioarylamide to an aryl ketone or aldehyde affords a lactone.Reduction of the latter with zinc and alkali or HI generates the free acid which undergoes cyclization with ZnCl2 and Ac2O and reduction with zinc and alkali or HI to furnish the fully aromatic polyarene.Compounds synthesized via this route include 3-methylcholanthrene, benzanthracene, dibenzanthracene, dibenzanthracene, benzopyrene, and their methyl derivatives.Overall yields are generally good.Competitive enolate anion formation depresses the yield in the initial step in the reactions of enolizable ketones.However, this pathway can be suppressed with substantial improvement in yield through deuterium exchange of the hydrogens α to the carbonyl.The last three steps of the general method can be condensed to only one step through reductive cyclization of the lactone intermediates with hydriodic acid in acetic acid.While tertiary lactones are resistant to HI under these conditions, the corresponding free acids undergo reductive cyclization under similar conditions.

SYNTHESIS OF 3-METHYLCHOLANTHRENE

A novel synthesis of 3-methylcholanthrene is described which is operationally simpler than the method in current use and is potentially applicable to the synthesis of a wide range of other polycyclic hydrocarbons and their oxidized carcinogenic metabolites.