78543-06-3

Basic information

• Product Name: diethyl (3-fluoro-4-nitrophenyl)methylmalonate
• Synonyms: diethyl (3-fluoro-4-nitrophenyl)methylmalonate;2-[(3-Fluoro-4-nitrophenyl)methyl]propanedioic acid diethyl ester
• CAS NO: 78543-06-3
• Molecular Formula: C₁₄H₁₆FNO₆
• Molecular Weight: 313.2783432
• EINECS: 278-942-9
• Mol File: 78543-06-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 411.1°C at 760 mmHg
• Flash Point: 202.4°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 5.75E-07mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: diethyl (3-fluoro-4-nitrophenyl)methylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (3-fluoro-4-nitrophenyl)methylmalonate(78543-06-3)
• EPA Substance Registry System: diethyl (3-fluoro-4-nitrophenyl)methylmalonate(78543-06-3)

Safety Data

• Hazardous Substances Data: 78543-06-3(Hazardous Substances Data)

Usage

General Description

Diethyl (3-fluoro-4-nitrophenyl)methylmalonate is an organic compound with the chemical formula C15H17NO7. It is a yellow solid that is commonly used as a reagent in organic synthesis. This chemical is often employed in the formation of various pharmaceutical and agrochemical products, as well as in the production of dyes and pigments. Diethyl (3-fluoro-4-nitrophenyl)methylmalonate is known for its ability to undergo Michael addition reactions, making it a valuable intermediate in the synthesis of complex organic molecules. Additionally, it has potential applications in the field of medicinal chemistry due to its ability to act as a structural mimic of biologically active molecules.

InChI:InChI=1/C14H16FNO6/c1-3-21-13(17)10(14(18)22-4-2)7-9-5-6-12(16(19)20)11(15)8-9/h5-6,8,10H,3-4,7H2,1-2H3

Upstream product

• 609-08-5 Diethyl methylmalonate 
• 446-35-5 2,4-Difluoronitrobenzene 

Downstream Products

• 5104-49-4 (S)-(+)-flurbiprofen 
• 5104-49-4 (R)-flurbiprofen 
• 81937-33-9 2-(4-amino-3-fluorophenyl)propionic acid 
• 42771-82-4 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid 
• 88975-70-6 2-[4-(3-Benzoyl-1-methyl-thioureido)-3-fluoro-phenyl]-2-methyl-malonic acid diethyl ester 
• 88975-54-6 2-[4-(3-Benzoyl-thioureido)-3-fluoro-phenyl]-2-methyl-malonic acid diethyl ester 
• 88975-32-0 2-[3-Fluoro-4-(2,2,2-trifluoro-acetylamino)-phenyl]-2-methyl-malonic acid diethyl ester 
• 93914-70-6 2-(3-Fluoro-4-thiocarbamoyloxy-phenyl)-2-methyl-malonic acid diethyl ester 
• 88975-89-7 2-(4-Cyanato-3-fluoro-phenyl)-2-methyl-malonic acid diethyl ester 
• 73120-17-9 2-[3-fluoro-4-(N-methyl-N-thiazol-2-ylamino)phenyl]-propionic acid 
• 88975-22-8 2-(3-Fluoro-4-methylamino-phenyl)-2-methyl-malonic acid diethyl ester 
• 88975-42-2 2-(3-Fluoro-4-hydroxy-phenyl)-2-methyl-malonic acid diethyl ester 
• 73120-15-7 2-[3-fluoro-4-(N-thiazol-2-ylamino)phenyl]propionic acid 
• 56355-37-4 2-(3-fluoro-4-thiazol-2-yloxy-phenyl)-propionic acid 

Relevant articles and documents

Improved preparation of flurbiprofen

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Flurbiprofen intermediate and preparation method thereof

The invention provides a flurbiprofen intermediate and a preparation method thereof, wherein the reaction formula is defined in the specification after a compound represented by a formula III is prepared by a coupling reaction between a substituted phenylacetamide compound and a compound represented by a general formula II, R1 and R2 are the same or different halogen, ester group, alkyl-substituted ester group and cyano, X is halogen, R4 is hydrogen, hydroxyl, halogen, nitro, alkyl, alkoxy, aryloxycarbonyl, cyano and cycloalkyl, and R is lowly-substituted alkyl. According to the present invention, the flurbiprofen or the derivative thereof can be prepared by carrying out the hydrolysis and the deamination according to the any sequence; and the route is environmentally friendly, and is suitable for industrial production.

Preparation of optically pure flurbiprofen via an integrated chemo-enzymatic synthesis pathway

In the synthesis of chiral molecules, the incorporation of enantioselective enzymatic conversions within the synthetic route often presents a useful approach. For the substitution of a chemical step with an enzymatic reaction, however, the complete synthetic route leading to and from this reaction needs to be considered carefully. An integrated approach, taking the possibilities and challenges of both types of conversions into account, can give access to chemo-enzymatic processes with great potential for effective synthesis strategies. We here report on the synthesis of enantiopure flurbiprofen using arylmalonate decarboxylase (AMDase, EC 4.1.1.76) in a chemo-enzymatic approach. Interestingly, practical considerations required shifting the enzymatic step to an earlier position in the synthetic route than previously anticipated. Engineered enzyme variants made it possible to obtain both (R)- and (S)-enantiomers of the target compound in excellent optical purity (>99%ee). The presented results underline that enzymes are most useful when they fit in a synthetic route, and that the optimization of biocatalytic steps and the planning of synthetic routes should be an integrated process.