98477-12-4

Basic information

• Product Name: ethyl 1-tert-butyl-5-cyano-1H-pyrazole-4-carboxylate
• Synonyms: ethyl 1-tert-butyl-5-cyano-1H-pyrazole-4-carboxylate;Ethyl 5-cyano-1-tert-butyl-1H-pyrazole-4-carboxylate;Ethyl 5-cyano-1-(1,1-dimethylethyl)-1H-pyrazole-4-carboxylate
• CAS NO: 98477-12-4
• Molecular Formula: C11H15N3O2
• Molecular Weight: 221.2557
• Mol File: 98477-12-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 362℃
• Flash Point: 173℃
• Appearance: /
• Density: 1.11
• Vapor Pressure: 1.95E-05mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ethyl 1-tert-butyl-5-cyano-1H-pyrazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-tert-butyl-5-cyano-1H-pyrazole-4-carboxylate(98477-12-4)
• EPA Substance Registry System: ethyl 1-tert-butyl-5-cyano-1H-pyrazole-4-carboxylate(98477-12-4)

Safety Data

• Hazardous Substances Data: 98477-12-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1293, 1988 DOI: 10.1002/jhet.5570250504

InChI:InChI=1/C11H15N3O2/c1-5-16-10(15)8-7-13-14(9(8)6-12)11(2,3)4/h7H,5H2,1-4H3

Upstream product

• 119741-57-0 3-cyano-1H-pyrazole-4-carboxylic acid ethyl ester 
• 98477-11-3 1-tert-Butyl-5-(hydroxyimino-methyl)-1H-pyrazole-4-carboxylic acid ethyl ester 
• 119741-57-0 5-cyano-1H-pyrazole-4-carboxylic acid, ethyl ester 
• 115-11-7 isobutene 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 119741-54-7 5-Aminocarbonyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 98477-08-8 1-(1,1-dimethylethyl)-5-methyl-1H-pyrazole-4-carboxylic acid 
• 98477-10-2 5-formyl-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester 
• 98477-09-9 5-(bromomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester 
• 127049-85-8 5-cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 623-91-6 diethyl Fumarate 
• 141-05-9 Diethyl maleate 
• 112779-11-0 5-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester 

Downstream Products

• 98477-07-7 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide 

Relevant articles and documents

1,3-Dipolar Cycloaddition as Applied to the Synthesis of 5-Cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide

The title compound was synthesized via 1,3-dipolar cycloaddition of diazoacetonitrile and diethyl fumarate.

Alkylation of 3(5)-cyano-1H-pyrazole-4-carboxylic acid esters

The present invention provides a process for selectively alkylating pyrazoles comprising reacting a 3(5)-cyano-1H-pyrazole-4-carboxylic acid ester with a C4 -C8 alkene, or a C5 -C6 cycloalkene substituted at the 1-position with a C1 -C4 alkyl group, and a strong acid in a solvent which contains a strong electron withdrawing group. Also provided are new 3(5)-cyano-1H-pyrazole-4-carboxylic acid ester useful as starting materials in the process of the invention.

Synthesis of 1-(1,1-Dimethylethyl)-1H-pyrazole-4-carboxylate Ester Derivatives

Attempts to prepare ethyl 5-cyano-1-(1,1-dimethylethyl)-1H-pyrazole-4-carboxylate (7) by the reaction of the corresponding 5-chloro derivative 1b with cyanide ion were unsuccessful.The chloro ester was synthesized from the corresponding amino ester 1a utilizing nonaqueous diazotization with nitrosyl chloride.An alternate process was developed which allowed the preparation of 7 from the corresponding 5-methyl ester 3 in four steps.The structure of N-methylamide 8 synthesized from 7 was confirmed by X-ray diffraction analysis.