39562-17-9

Basic information

• Product Name: Methyl 3-nitrobenzylideneacetoacetate
• Synonyms: METHYL 2-(M-NITROBENZYLIDENE)-ACETOACETATE;Methyl 3-nitrobenzylideneacetoacetate;methyl 2-(3-nitrobenzylidene)-acetoacetate;ETHYL 3-NITROBENZYLIDENACETOACETATE;2-(3-NITROBENZYLIDENE)ACETOACETIC ACID METHYL ESTER;2-[(3-Nitrophenyl)methylene]-3-oxo-butanoic acid methyl ester;SALOR-INT L133515-1EA;Methyl 2-(3-nitrobenzylidene)-3-oxobutanoate
• CAS NO: 39562-17-9
• Molecular Formula: C₁₂H₁₁NO₅
• Molecular Weight: 249.22
• EINECS: 405-270-7
• Product Categories: Organic acids;(intermediate of nitrendipine)
• Mol File: 39562-17-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 158°C
• Boiling Point: 387°C
• Flash Point: 172°C
• Appearance: /
• Density: 1.296
• Vapor Pressure: 3.27E-06mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• Solubility: Chloroform; Dichloromethane; DMSO
• CAS DataBase Reference: Methyl 3-nitrobenzylideneacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-nitrobenzylideneacetoacetate(39562-17-9)
• EPA Substance Registry System: Methyl 3-nitrobenzylideneacetoacetate(39562-17-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 24-37-60-61
• Hazardous Substances Data: 39562-17-9(Hazardous Substances Data)

Usage

Uses

Methyl 2-(3-Nitrobenzylidene)-3-oxobutanoate is a useful reactant in organic synthesis.

InChI:InChI=1/C12H11NO5/c1-8(14)11(12(15)18-2)7-9-4-3-5-10(6-9)13(16)17/h3-7H,1-2H3/b11-7+

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 93181-50-1 4,7-dihydro-1,3,6-trimethyl-4-(3-nitrophenyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid methyl ester 
• 111634-72-1 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester 
• 21881-77-6 m-nifedipine 
• 168902-10-1 (+/-)-MN₉₂₀₂ 
• 225785-54-6 3-methyl 5-n-propyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 39562-70-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester 
• 88284-34-8 5-n-dodecyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 88284-23-5 3-methyl 5-n-octyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 1137518-89-8 5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 96996-36-0 1,3,7-Trimethyl-5-(3-nitro-phenyl)-4-oxo-2-thioxo-1,2,3,4,5,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid methyl ester 
• 92388-31-3 4,7-dihydro-1,6-dimethyl-4-(3-nitrophenyl)-3-(n-butyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester 
• 118431-16-6 methyl 1,3-dicyclopentyl-6-methyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate 
• 92406-26-3 methyl 3-(3,5-dichlorophenyl)-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate 
• 97820-60-5 1,6-Dimethyl-3-(1-methyl-pyrrolidin-2-yl)-4-(3-nitro-phenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester 

Relevant articles and documents

Preparation method of benidipine hydrochloride

The invention belongs to the field of chemical synthesis of drugs, and particularly relates to a preparation method of a hypotensive drug benidipine hydrochloride. The method comprises the following steps: carrying out a Knoevenagel reaction, a Michael addition reaction, cyclization and hydrolysis on starting raw materials 3-nitrobenzaldehyde and methyl acetoacetate in the presence of a catalyst, reacting with thionyl chloride, directly reacting with 1-benzyl-3-hydroxypiperidine, and refining to obtain the benidipine hydrochloride. The benidipine hydrochloride obtained by adopting the preparation method of the benidipine hydrochloride is high in purity, column chromatography isolation is not needed, and the HPLC purity of the product is 99.5% or above. The yield of the obtained benidipine hydrochloride is relatively high and can reach 68% or above.

An expedient synthesis of β-acetamido- and β-benzamidocarbonyl compounds via KAL(SO4)2·12H2O-catalyzed three-component coupling reaction

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Synthesis and antihypertensive activity evaluation in spontaneously hypertensive rats of nitrendipine analogues

The antihypertensive activity of nitrendipine analogues can be improved by properly lengthening its alkyl chain in 3- or 5-position. Nitrendipine and its seven analogues were synthesized, and their antihypertensive activities in spontaneously hypertensive rats (SHR) were evaluated by ig administration. It was found that 5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4- dihydropyridine- 3,5-dicarboxylate [(±)-5] exhibited the strongest antihypertensive effect amongst eight compounds. (?)-5-nheptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylate [(+)-5] was also prepared. Antihypertensive activities of (±)-5 and (?)-5 in SHR were compared. The results showed that (±)-5 and (?)-5 had a higher potency than nitrendipine, and (+)-isomer was 1.79-fold the raceme at a dose of 2 mg/kg. Springer Science+Business Media, LLC 2010.