595-46-0

Usage

Uses

Used in Pharmaceutical Industry:
Dimethylmalonic acid is used as an intermediate in the synthesis of various pharmaceutical compounds, such as vitamins, antibiotics, and other therapeutic agents. Its unique chemical structure allows for the development of novel drugs with potential applications in treating various diseases.
Used in Chemical Synthesis:
Dimethylmalonic acid serves as a key building block in the synthesis of various organic compounds, including specialty chemicals, dyes, and polymers. Its versatile reactivity and functional groups make it a valuable component in the chemical industry.
Used in Nutritional Supplements:
As a component of certain metabolic pathways, dimethylmalonic acid can be used in the formulation of nutritional supplements to support overall health and well-being. It may play a role in energy production and the maintenance of healthy cellular functions.
Used in Research and Development:
Dimethylmalonic acid is utilized in research laboratories for studying various biological processes and mechanisms. Its unique properties make it an interesting subject for scientific investigation, potentially leading to new discoveries and applications in medicine and other fields.

Purification Methods

Crystallise the acid from *benzene/pet ether. It sublimes in a vacuum with slight decomposition. [Beilstein 2 IV 1955.]

InChI:InChI=1/C5H8O4/c1-5(2,3(6)7)4(8)9/h1-2H3,(H,6,7)(H,8,9)

Upstream product

• 600-00-0 ethyl 2-bromoisobutyrate 
• 151-50-8 potassium cyanide 
• 116070-49-6 dimethyl malonamic acid 
• 2437-52-7 3-tert-Butyl-2,4,4-trimethyl-pent-2-ene 
• 38923-57-8 methyl 2,2-dimethyl-3-oxobutanoate 
• 143688-40-8 t-butyl dimethylmalonate 
• 1195-79-5 1,3,3-trimethyl-2-norbornanone 
• 7556-50-5 4,4,4',4',7,7'-hexamethyl-2,2'-spirobichroman 
• 1066-30-4 chromium(lll) acetate 
• 1619-62-1 2,2-dimethylmalonic acid diethyl ester 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 1623-99-0 phenyl sodium 
• 79-31-2 isobutyric Acid 
• 71-43-2 benzene 

Downstream Products

• 72708-59-9 2,2-dimethyl-3-oxo-3-(phenylamino)propanoic acid 
• 24448-94-0 5,5-dimethylbarbituric acid 
• 57186-07-9 4,4-dimethyl-1-phenylpyrazolidine-3,5-dione 
• 62214-48-6 1,4,4-trimethyl-2-phenyl-pyrazolidine-3,5-dione 
• 79-31-2 isobutyric Acid 
• 15719-64-9 methylammonium carbonate 
• 5659-93-8 2,2-Dimethylmalonyl chloride 
• 77463-49-1 bis(benzoylmethyl) 2,2-dimethylpropane-1,3-dioate 
• 13051-21-3 3-methoxy-2,2-dimethyl-3-oxopropanoic acid 
• 57772-82-4 dibenzyl dimethylmalonate 
• 92367-59-4 3,3-dimethyl-3,4-dihydroquinolin-2(1H)-one 
• 94844-02-7 N-phenyl-2-(hydroxymethyl)-2-methylpropylamine 
• 112565-64-7 2,2-dimethyl-N-phenyl-3-p-tolylsulphonyloxypropionamide 
• 112565-63-6 N-(2,2-dimethyl-3-p-tolylsulphonyloxypropyl)-N-phenyltoluene-p-sulphonamide 

Relevant academic research and scientific papers

Method for continuous-flow preparation of 2,2-dimethylmalonic acid

The invention provides a method for continuous-flow preparation of 2,2-dimethylmalonic acid. According to the method, a micro-channel reactor is utilized, a 2,2-dimethyl propylene glycol solution is used as a material 1, nitric acid is used as a material 2, and the materials are introduced into the micro-channel reactor for continuous-flow synthesis of 2,2-dimethylmalonic acid, wherein the reaction temperature is 30-100 DEG C, and the reaction time is 20-100 s. Compared with a conventional tank reactor in the prior art, the method provided by the invention has the advantages that the reactiontime is greatly shortened, mass transfer and heat transfer are uniform, the amplification effect is avoided, and the yield is improved to a certain extent compared with a tank reaction; more importantly, a liquid holding volume of the method is small, so the potential risk of nitric acid oxidation is greatly reduced; and the safety and operability of the method are improved.

Preparation and Characterisation of a Bis-μ-Hydroxo-NiIII 2 Complex

Hydroxide-bridged high-valent oxidants have been implicated as the active oxidants in methane monooxygenases and other oxidases that employ bimetallic clusters in their active site. To understand the properties of such species, bis-μ-hydroxo-NiII 2 complex (1) supported by a new dicarboxamidate ligand (N,N′-bis(2,6-dimethyl-phenyl)-2,2-dimethylmalonamide) was prepared. Complex 1 contained a diamond core made up of two NiII ions and two bridging hydroxide ligands. Titration of the 1 e? oxidant (NH4)2[CeIV(NO3)6] with 1 at ?45 °C showed the formation of the high-valent species 2 and 3, containing NiIINiIII and NiIII 2 diamond cores, respectively, maintaining the bis-μ-hydroxide core. Both complexes were characterised using electron paramagnetic resonance, X-ray absorption, and electronic absorption spectroscopies. Density functional theory computations supported the spectroscopic assignments. Oxidation reactivity studies showed that bis-μ-hydroxide-NiIII 2 3 was capable of oxidizing substrates at ?45 °C at rates greater than that of the most reactive bis-μ-oxo-NiIII complexes reported to date.

Photodegradation of Myrigalone A, an Allelochemical from Myrica gale: Photoproducts and Effect of Terpenes

This study investigated the environmental fate of myrigalone A, a light absorbing natural herbicide found on leaves and fruits of Myrica gale. Myrigalone A was irradiated in water and as a dry solid deposit to simulate reactions on leaves, alone and in the presence of the terpenes generated by Myrica gale. The phototransformation was fast (t1/2 = 35 min in water). Analyses by liquid chromatography coupled to high resolution orbitrap electrospray mass spectrometry (MS) and gas chromatography-MS revealed the formation of 11 photoproducts in water and solid and 9 in gaseous phase. Some were detected in the leaf glands and oil covering the fruits of Myrica gale, which suggested that photodegradation occurred in the field. Moreover, myrigalone A photoinduced the oxidation of terpenes that in turn protected it against photolysis. This highlights the need for additional research on the effect of terpenes on the photodegradation of pesticides on vegetation.

Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect

A series of malonamides possessing two quinoline moieties were synthesized and characterized as fluoroionophores for the Zn2+ ion. We focused on the relationship between the substituents introduced to the C2-position of the malonamides and their Zn2+ ion-selectivity, exploiting the structural effect of the substituents in the design of the fluoroionophores with high selectivity. The substituents introduced to the malonamides were the methyl, benzyl and naphthalenylmethyl groups. In dimethyl sulfoxide solvent, all substituted bisquinolinyl malonamides showed excellent fluorescence sensing for the Zn2+ ion, while unsubstituted bisquinolinyl malonamide 1 displayed ratiometric sensing for the Co2+ ion. N,N′-Bis(8-quinolyl)-2-methyl-2-naphthalenylmethyl malonamide 4 exhibited the highest Zn2+ ion-selectivity against the Cd2+ ion. Although the substituents introduced into the C2-position are spatially distant from the quinoline recognition moiety, this study indicated that they greatly influenced the ion selectivities of the bisquinolinyl malonamides. Furthermore, it was demonstrated that visible fluorescence analyses could be performed on malonamide 4.

Microwave assisted hydrolysis of Meldrum's acid derivatives and decarboxylation of derived malonic acids

Microwave induced hydrolysis of alkyl Medrum's acids and decarboxylation of derived malonic acids using poly-4-vinylpyridine as a catalyst gives high yields of carboxylic acids in a short time.

Process for preparing malonic acid and alkylmalonic acids

Malonic acid and alkylmalonic acids are prepared by a process of acid-catalyzed saponification of malonic acid esters, which comprises: contacting an aqueous mixture of the ester II with an acid ion exchanger containing sulfonic acid groups at from 30°-100° C. and from 40-1000 mbar according to the following scheme: STR1 where R1 =H, CH3, R2 =H, CH3 or R1 +R2 =--CH2 --CH2 --and R3 =CH3, C2 H5, C3 H7, C(CH3)3 ; distilling off the alcohol R3 OH which is formed; separating the water, with the aid of organic solvents, from the malonic acid or alkylmalonic acid product; and then isolating the product by crystallization.

RETROVIRAL PROTEASE INHIBITORS

Urea-containing hydroxyethylamine peptide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

Ligandgesteuerte Ringkontraktion von Nickela-Fuenf- in Vierringkomplexe-neuartige Startsysteme fuer die praeparative Chemie

Nickela-compounds with a five-membered ring, 4, are formed on Ni0 from CO2 and alkenes in the presence of the heterodifunctional ligand (cyclo-C6H11)2PCH2-CH2-2-pyridyl (2).A ring contraction occurs on addition of a promotor, such as BeCl2 or on heating.The greater reactivity of the nickela-complex with a four-membered ring, 6, can be used in the former reactions with CO2, CO or CH2=CH2.Such a sequence of reactions can be employed for the catalytic reaction of ethene with acrylic anilide on a (C6H11)3P/Ni0 system.

The E1cb Route for Ester Hydrolysis; Volumes of Activation as an Additional Criterion of Mechanism

Hydrolyses of esters which possess an acidic proton at the α or vinylogous position can, in principle, hydrolyse by the E1cb route via a ketenoid intermediate.To the kinetic evidence for such a mechanism in the hydrolyses of 4-hydroxybenzoates, malonates, acetoacetates and fluorenecarboxylates is now added the further criterion of volumes of activation.Values of ΔV(excit.) for reactions proceeding by the E1cb route are positive and contrast with the negative values associated with hydrolyses by the more usual BAc2 mechanism.

The Nitration of 3,4,5,6-Tetramethylbenzene-1,2-dicarbonitrile, 2,3,5,6-Tetramethylbenzonitrile, 1,2,3-Trimethyl-4,6-dinitrobenzene and 1,2,4,5-Tetramethyl-3,6-dinitrobenzene. Methyl Migrations Following ipso-Substitution

Nitration of 3,4,5,6-tetramethylbenzene-1,2-dicarbonitrile (1a) gives epimeric pairs of dinitro ketones (6a) and (7a), and hydroxy ketones (9) and (10), in addition to the benzyl nitrate (4) and phthalide (5).Nitration of 2,3,5,6-tetramethylbenzonitrile (11) gives the epimeric dinitro ketones (15) and (16), in addition to the nitrobenzonitrile (12) and the nitrophthalide (13).Nitration of 1,2,3-trimethyl-4,6-dinitrobenzene (17) gives dimethylpropanedioic acid (23), the dinitrobenzoic acid (24), and the hydroxy dienone (25).Nitration of 1,2,4,5-tetramethyl-3,6-dinitrobenzene (18) gives dimethylpropanedioic acid (23), the dinitrobenzoic acid (26), and the nitro dicarboxylic acid (27).The formation of compounds (6a), (7a), (9), (10), (15), (16), (23) and (27) all involve methyl migrations following nitronium ion attack ipso to the migrating methyl group.X-Ray structure determinations are reported for compounds (6a), (9) and (15).