22035-53-6

Basic information

• Product Name: dimethyl isopropylidenemalonate
• Synonyms: dimethyl isopropylidenemalonate;dimethyl 2-(propan-2-ylidene)malonate;2-(1-Methylethylidene)propanedioicacid 1,3-dimethyl ester;Isopropylidene-Malonic Acid DiMethyl Ester;dimethyl isopropylidenemalote;dimethyl 2-propan-2-ylidenepropanedioate
• CAS NO: 22035-53-6
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• Product Categories: Aliphatics;Miscellaneous Reagents
• Mol File: 22035-53-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 179℃
• Flash Point: 76℃
• Appearance: /
• Density: 1.070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Acetone, Chloroform, Dichloroemethane, Ethyl Acetate
• CAS DataBase Reference: dimethyl isopropylidenemalonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl isopropylidenemalonate(22035-53-6)
• EPA Substance Registry System: dimethyl isopropylidenemalonate(22035-53-6)

Safety Data

• Hazardous Substances Data: 22035-53-6(Hazardous Substances Data)

Usage

Description

Dimethyl isopropylidenemalonate is a colorless oil with unique chemical properties that make it a valuable compound in various applications. It is an organic compound derived from the malonate family, characterized by its isopropylidene group and two methyl ester groups.

Uses

Used in Pharmaceutical Industry:
Dimethyl isopropylidenemalonate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Cancer Treatment:
Dimethyl isopropylidenemalonate is used as a precursor in the preparation of inhibitors of indoleamine 2,3-dioxygenase (IDO). These inhibitors have shown promise in the treatment of cancer, as they can modulate the immune system and potentially slow down tumor growth.
Used in Chemical Synthesis:
As a colorless oil, dimethyl isopropylidenemalonate serves as a versatile building block in the synthesis of various organic compounds. Its reactivity and functional groups make it a valuable component in the development of new chemicals and materials.

Upstream product

• 67-64-1 acetone 
• 108-59-8 malonic acid dimethyl ester 
• 187737-37-7 propene 
• 18424-76-5 dimethyl malonate sodium salt 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 17640-15-2 methyl cyanoformate 
• 110622-26-9 2,4-Bis-methoxycarbonyl-3,3-dimethyl-pentanedioic acid dimethyl ester 
• 67-56-1 methanol 

Downstream Products

• 57090-81-0 2-(1,1-Dimethyl-2,2-diphenyl-ethyl)-malonic acid dimethyl ester 
• 148904-67-0 2-((2E,4E)-1-Methyl-5-phenyl-penta-2,4-dienylidene)-malonic acid 
• 39520-25-7 tert-Butylmalonsaeure-dimethylester 
• 133475-87-3 2,6,6-Trimethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 133475-91-9 (2R,5S)-2,5,6,6-Tetramethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 133475-88-4 6,6-Dimethyl-4-(4-methyl-pent-3-enyl)-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 133475-90-8 2,4,6,6-Tetramethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 51122-91-9 dimethyl isopropylmalonate 
• 28010-27-7 2-((E)-1-Methyl-3-phenyl-allylidene)-malonic acid 
• 133475-89-5 3,4,6,6-Tetramethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 133475-86-2 4,6,6-Trimethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 133494-04-9 dimethyl 3,3-dimethoxybutane-1,1-dicarboxylate 
• 170464-48-9 Methyl 2-(methoxycarbonyl)-3-methyl-3-phenylbutanoate 
• 24889-15-4 methyl 2-(methoxycarbonyl)-4-oxopentanonate 

Relevant articles and documents

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α-Carboxy-β-lactones from photoinduced ring contraction of 3-diazodihydrofuran-2,4-diones

β-Lactones were prepared by irradiation of 3-diazodihydrofuran-2,4- diones via Wolff rearrangement proceeding with retention of the configuration of the migrating carbon atom. In the presence of alcohols or thiols, but not amines, the corresponding 3-(alkoxycarbonyl)- or 3-[(alkylsulfanyl)carbonyl]- β-lactones were obtained. 5-Alkyl-3-diazodihydrofuran-2,4-diones gave exclusively trans-3,4-disubstituted β-lactones. Georg Thieme Verlag Stuttgart · New York.

Substituent Effects on the C-C Bond Strength, 19. Geminal Substituent Effects, 10. Radical Stabilization Enthalpies of α,α-Bis(methoxycarbonyl)alkyl and Tris(methoxycarbonyl)methyl Radicals

Heats of formation ΔH0f(g) were determined from enthalpies of combustion ΔH0f(c) and enthalpies of vaporization ΔH0vap or sublimation ΔH0sub for the eight substituted methanetricarboxylates 2a-h.From these data and from previously determined enthalpies of formation ΔH0f of substituted malonic esters new thermochemical group increments were derived.From these increments and from the recently published improved increments for carboxylic acid esters the gem. interaction enthalpies of two and three COOR groups were calculated.The radical stabilization enthalpies RSE of α,α-bis(methoxycarbonyl)alkyl (18.2 kJ mol-1, 1a) and tris(methoxycarbonyl)methyl radicals (5.2 kJ mol-1, 1b) were derived from kinetic data obtained by means of our previously developed protocol.They were corrected for the gem. interaction energies of the ester groups in the ground state and are satisfactorily explained by an additive stabilizing effect for the ester substituents and by dipolar substituent interactions in the radicals.The dipolar energies were taken from MM2 calculations. - Keywords: Enthalpies of formation / Geminal substituents, energetic interaction of / Bond cleavage, C-C, kinetics of / Radicals, stabilization of / Increments, thermochemical, of esters