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

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 
• 112779-11-0 5-(hydroxyiminomethyl)-1-tert-butyl-1H-pyrazole-4-carboxylic acid, ethyl ester 
• 141-05-9 Diethyl maleate 
• 623-91-6 diethyl Fumarate 
• 127049-85-8 5-cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 98477-09-9 5-(bromomethyl)-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.

Carbon-13 NMR Chemical Shifts of 1-Alkyl-3(5)-cyano-1H-pyrazole-4-carboxylic Acid Esters

A compilation of 13C NMR chemical shifts for 13 pairs of 3- and 5-cyano-substituted pyrazole regioisomers is reported.All of the ring carbon and cyano carbon 13C chemical shifts show a regular, predictable correlation with the particular isomer, whether 3-cyano or 5-cyano.These shifts occured in very narrow ranges, precluding any confusion of assignment within the group of compounds studied.X-ray crystallographic analysis was performed on one of the samples.

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.

A Novel Regioselective t-Butylation as Applied to the Synthesis of 5-Cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide

The title compound was synthesized in a regiocontrolled way from 5-cyano-1H-pyrazole-4-carboxylic acid, ethyl ester (5) with isobutylene, p-toluenesulfonic acid and methylamine.

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.

Herbicidal and algicidal 1-aryl-5-cyano-1H-pyrazole-4-carboxamides

The present invention is directed to compounds of the formula STR1 wherein R1 is C1 -C6 alkyl, C5 -C6 cycloalkyl, STR2 each of R2 and R3 is taken separately and is independently

Cyanopyrazole intermediates

5-Cyano-1-substituted-1H-pyrazole-4-carboxylic acids and esters useful as intermediates to the corresponding 4-carboxyamide derivatives having herbicidal and algicidal activity.