74073-22-6

Basic information

• Product Name: Methyl 2-(2,3-dichlorobenzylidine)acetoacetate
• Synonyms: METHYL-2-(2,3-DICHLORBENZYLIDEN)-ACETOACETATE;2,3-Dichlorobenzylideneaceto;METHYL 2-(2,3-DICHLOROBENZYLIDINE)ACETOACETATE;2-[(2,3-Dichlorophenyl)methylene]-3-oxobutanoic acid methyl ester;BUTANOICACID,2-[(2,3-DICHLOROPHENYL)METHYLENE]-3-OXO-,METHYLESTER(9CI);2-nitro-4-methylsulfonyl benzoyl chloride;Methyl 2-(2,3-dichlo;Methyl 2-(2,3-Dichlorobenzylidene)acetoacetate
• CAS NO: 74073-22-6
• Molecular Formula: C₁₂H₁₀Cl₂O₃
• Molecular Weight: 273.11
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Intermediates
• Mol File: 74073-22-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 81-83 °C
• Boiling Point: 383.6 °C at 760 mmHg
• Flash Point: 157.1 °C
• Appearance: /
• Density: 1.337
• Vapor Pressure: 4.35E-06mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl 2-(2,3-dichlorobenzylidine)acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(2,3-dichlorobenzylidine)acetoacetate(74073-22-6)
• EPA Substance Registry System: Methyl 2-(2,3-dichlorobenzylidine)acetoacetate(74073-22-6)

Safety Data

• Hazardous Substances Data: 74073-22-6(Hazardous Substances Data)

Usage

Description

Methyl 2-(2,3-dichlorobenzylidine)acetoacetate is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which features a methyl group, an acetoacetate moiety, and a 2,3-dichlorobenzylidine group. Methyl 2-(2,3-dichlorobenzylidine)acetoacetate plays a significant role in the development of dihydropyridine calcium antagonists, which are essential in the treatment of cardiovascular diseases.

Uses

Used in Pharmaceutical Industry:
Methyl 2-(2,3-dichlorobenzylidine)acetoacetate is used as a key intermediate in the synthesis of dihydropyridine calcium antagonists for the treatment of cardiovascular diseases. These antagonists are known to relax blood vessel walls, leading to improved blood flow and reduced blood pressure. Methyl 2-(2,3-dichlorobenzylidine)acetoacetate's unique structure allows for the development of effective medications that can help manage and treat conditions such as hypertension, angina, and certain heart arrhythmias.

InChI:InChI=1/C12H10Cl2O3/c1-7(15)9(12(16)17-2)6-8-4-3-5-10(13)11(8)14/h3-6H,1-2H3/b9-6+

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 6334-18-5 2,3-dichlorobenzylaldehyde 

Downstream Products

• 96918-80-8 cyclopropylmethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 
• 110962-94-2 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate methyl ester-(2-cyanoethyl)ester 
• 72509-76-3 ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate 
• 123853-39-4 (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid 
• 74073-26-0 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate-(tert-butyl) methylester 
• 101411-53-4 4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-2-(2-hydroxyethoxymethyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine 

Relevant articles and documents

An efficient and recyclable 3D printed α-Al2O3 catalyst for the multicomponent assembly of bioactive heterocycles

A catalytic methodology is reported that enables the efficient, operationally simple and environmentally friendly synthesis of diverse 1,4-dihydropyridines and 3,4-dihydropyrimidin-2(1H)-ones, including some relevant drugs and pharmacologically active derivatives. This strategy is based on the use of a 3D printed Al2O3 woodpile material that was sintered to generate a rigid structure with controlled porosity and noteworthy catalytic performance. The 3D printed Al2O3 catalyst exhibits remarkable efficacy as a Lewis acid in Biginelli and Hantzsch reactions and it can be recovered and reused ten times without any decrease in the activity. Remarkable E factors, excellent recyclability and scalability, broad substrate scope, short reaction times, excellent yields, solvent-free conditions and easy isolation procedures are key features of this methodology.