16695-14-0

Basic information

• Product Name: MONOMETHYL MALONATE
• Synonyms: AURORA KA-6464;MONOMETHYL MALONATE;Methyl hydrogen malonate, 96%;1-Methyl malonate;Malonic acid 1-hydrogen 3-methyl ester;Malonic acid hydrogen 1-methyl ester;3-methoxy-3-oxopropanoic acid;(Methoxycarbonyl)acetic acid
• CAS NO: 16695-14-0
• Molecular Formula: C₄H₆O₄
• Molecular Weight: 118.09
• Product Categories: Miscellaneous Reagents
• Mol File: 16695-14-0.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 232℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.128
• Refractive Index: 1.428
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.83±0.32(Predicted)
• CAS DataBase Reference: MONOMETHYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: MONOMETHYL MALONATE(16695-14-0)
• EPA Substance Registry System: MONOMETHYL MALONATE(16695-14-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 16695-14-0(Hazardous Substances Data)

Usage

Description

MONOMETHYL MALONATE is a clear liquid that serves as a reagent in chemical reactions, particularly in the lactonization of olefins. It is commonly used in conjunction with ceric ammonium nitrate (CAN) to facilitate the process, which can be carried out in solvents such as acetic acid or acetonitrile. The use of ultrasound irradiation in this reaction can lead to an acceleration compared to the mechanically stirred process.

Uses

Used in Chemical Synthesis:
MONOMETHYL MALONATE is used as a reagent in the lactonization of olefins, a chemical reaction that involves the formation of a cyclic ester from an olefin and a carboxylic acid. This process is essential in the synthesis of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, MONOMETHYL MALONATE is used as a key intermediate in the synthesis of drugs and drug candidates. Its ability to participate in lactonization reactions allows for the creation of complex molecular structures that can exhibit therapeutic properties.
Used in Research and Development:
MONOMETHYL MALONATE is utilized in research and development settings to explore new chemical reactions and synthesize novel compounds. Its versatility in participating in lactonization reactions makes it a valuable tool for chemists working on the design and synthesis of new molecules with potential applications in various fields.
Used in Environmental Applications:
Although not explicitly mentioned in the provided materials, MONOMETHYL MALONATE may also find use in environmental applications, such as the synthesis of biodegradable polymers or the development of green chemistry processes that minimize waste and reduce environmental impact.

Upstream product

• 67-56-1 methanol 
• 105-53-3 diethyl malonate 
• 16501-24-9 S,S'-diethyl dithiomalonate 
• 141-82-2 malonic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 51849-23-1 Methyl trimethylsilyl malonate 
• 591-12-8 5-methyl-2-furanone 
• 108-59-8 malonic acid dimethyl ester 
• 38330-80-2 monomethyl monopotassium malonate 
• 7732-18-5 water 
• 17041-60-0 dimethyl ethylidenemalonate 

Downstream Products

• 1664-59-1 3-(3-nitrophenyl)acrylic acid methyl ester 
• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 42726-73-8 methyl t-butyl malonate 
• 207919-13-9 cis-caffeic acid methyl ester 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 6932-46-3 (2Z,4E)-hexadienoic acid methyl ester 
• 32775-94-3 methyl (E)-3,5-hexadienoate 
• 106183-37-3 methyl 3-<2'-(2''-thienyl)phenyl>3-oxopropanoate 
• 155257-35-5 N-benzyl-N-(4-methylphenyl)-α-carbomethoxyacetamide 
• 64252-49-9 (E)-4-Phenyl-2-pentensaeure-methylester 
• 67376-72-1 (2R,3S)-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione 
• 155257-32-2 N-(methoxycarbonylethyl)-N-(4-methoxyphenyl)-α-carbomethoxyacetamide 
• 155257-30-0 N-benzyl-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide 
• 155257-37-7 N-butyl-N-(4-methoxycarbonylphenyl)-α-carbomethoxyacetamide 

Relevant articles and documents

PHOTOCHEMISTRY OF 1,3-DIMETHYLURACIL. A NOVEL PHOTOCHEMICAL RING-OPENING LEADING TO AN ENAMINE

Besides known reduction and solvent addition products, the photolysis of 1,3-dimethyluracil in methanol resulted in formation of the enamine 2-methoxycarbonyl-N-methyl-3-methylaminopropenamide (5) via a novel ring-opening reaction.A mechanism for the formation of 5 is suggested and its structure was confirmed by an independent synthesis.

Method for preparing diacid diester compound under catalysis of deep eutectic solvent

The invention belongs to the technical field of organic synthesis, and discloses a method for preparing a diacid diester compound through catalysis of a deep eutectic solvent, wherein the deep eutectic solvent takes ammonium salt and ferric salt as hydrogen acceptors, takes p-toluenesulfonic acid as a hydrogen donor, takes diacid or anhydride of the diacid and an alcohol compound as raw materials, and adopts a one-pot method to prepare the diacid diester compound; and under the catalysis of the deep eutectic solvent, the esterification reaction is performed to generate the diester product. The selected deep eutectic solvent has characteristics of environmental protection, easy preparation, cheap components and easy recovery; the preparation method has characteristics of simple operation, simple separation, no water-carrying agent, repeated use of the deep eutectic solvent, and high diester yield.

A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids

A Br?nsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network was formed by self-condensation of dodecatungstophosphoric acid and a zwitterionic organosilane precursor containing both imidazolinium and sulfonate groups. The resulting hybrid material POS-HPA-IL was investigated as a catalyst for the selective esterification of dicarboxylic acids.

Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.