17669-30-6

Basic information

• Product Name: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester
• Synonyms: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester
• CAS NO: 17669-30-6
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.246
• Mol File: 17669-30-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 371.3°Cat760mmHg
• Flash Point: 165.7°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.04E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(17669-30-6)
• EPA Substance Registry System: 4,5-Dihydro-3-phenylisoxazole-4,5-dicarboxylic acid dimethyl ester(17669-30-6)

Safety Data

• Hazardous Substances Data: 17669-30-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13NO5/c1-17-12(15)9-10(8-6-4-3-5-7-8)14-19-11(9)13(16)18-2/h3-7,9,11H,1-2H3

Upstream product

• 873-67-6 benzonitrile oxide 
• 624-49-7 dimethylfumarate 
• 186581-53-3 diazomethane 
• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid 
• 67-56-1 methanol 
• 17669-30-6 Z-dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate 
• 124-41-4 sodium methylate 
• 698-16-8 benzohydroximoyl chloride 
• 28198-51-8 potassium salt of phenyldinitromethane 
• 622-42-4 1-nitro-1-phenylmethane 
• 25327-36-0 (Z)-2-(hydroxyimino)-2-phenylacetic acid 
• 23055-10-9 1,4-dimethyl but-2-enedioate 
• 611-73-4 Benzoylformic acid 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 

Downstream Products

• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid 
• 17669-30-6 dimethyl 3-phenyl-4,5-dihydroisoxazole-4,5-dicarboxylate 
• 99972-90-4 (+/-)-3-phenyl-4,5-dihydro-isoxazole-4r,5c-dicarboxylic acid 
• 4872-58-6 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid 
• 100-47-0 benzonitrile 
• 35053-78-2 3-phenyl-4,5-dihydro-isoxazole-4r,5t-dicarboxylic acid diamide 

Relevant articles and documents

Electrochemical Synthesis of Isoxazolines: Method and Mechanism

An electrochemical method for the green and practical synthesis of a broad range of substituted isoxazoline cores is presented. Both aryl and more challenging alkyl aldoximes are converted to the desired isoxazoline in an electrochemically enabled regio- and diastereoselective reaction with electron-deficient alkenes. Additionally, in-situ reaction monitoring methods compatible with electrochemistry equipment have been developed in order to probe the reaction pathway. Supporting analyses from kinetic (time-course) modelling and density functional theory support a stepwise, radical-mediated mechanism, and discounts hypothesised involvement of closed shell [3+2] cycloaddition pathways.

Pd Catalysis in Cyanide-Free Synthesis of Nitriles from Haloarenes via Isoxazolines

A method to obtain aryl nitriles from the corresponding halides by Pd catalysis, in the absence of any cyanide source, is reported. The reaction of an aryl halide, ethyl nitroacetate, and an olefin readily delivers an aromatic nitrile. A variety of aryl iodides/bromides have been converted into the corresponding cyanoarenes in fair to excellent yields. The reaction likely involves the following steps: (a) Pd-catalyzed α-arylation of ethyl nitroacetate; (b) nitrile oxide formation; (c) [3 + 2]-cycloaddition with an olefin to provide an isoxazoline; (d) isoxazoline cleavage to benzonitrile formation.

Conversion of oximes to carbonyl compounds by triscetylpyridinium tetrakis(oxodiperoxotungsto) phosphate (PCWP)-mediated oxidation with hydrogen peroxide

Aromatic and aliphatic oximes have been deoximated in chloroform-water to the corresponding aldehydes with dilute hydrogen peroxide and triscetylpyridinium tetrakis (oxodiperoxotungsto) phosphate as catalyst. The presence of dipolarophiles in the reaction mixtures allows a competitive reaction that converts oximes into isoxazole and isoxazoline derivatives via the intermediate formation of nitrile oxide species.