7007-08-1

Basic information

• Product Name: 3,5-dimethyl-1-(1-methylethyl)-1H-pyrazole-4-carboxylic acid
• Synonyms: 1H-pyrazole-4-carboxylic acid, 3,5-dimethyl-1-(1-methylethyl)-; 1-Isopropyl-3,5-dimethyl-1H-pyrazole-4-carboxylic acid; 3,5-dimethyl-1-(propan-2-yl)-1H-pyrazole-4-carboxylic acid
• CAS NO: 7007-08-1
• Molecular Formula: C₁₅H₁₀BrNO
• Molecular Weight: 182.2197
• Mol File: 7007-08-1.mol

Chemical Properties

• Boiling Point: 306°C at 760 mmHg
• Flash Point: 138.9°C
• Density: 1.17g/cm³
• Vapor Pressure: 0.000345mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 3,5-dimethyl-1-(1-methylethyl)-1H-pyrazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dimethyl-1-(1-methylethyl)-1H-pyrazole-4-carboxylic acid(7007-08-1)
• EPA Substance Registry System: 3,5-dimethyl-1-(1-methylethyl)-1H-pyrazole-4-carboxylic acid(7007-08-1)

Safety Data

• Hazardous Substances Data: 7007-08-1(Hazardous Substances Data)

Upstream product

• 18735-78-9 2,5-diphenyloxazole-4-carboxylic acid 
• 39819-39-1 2-phenyl-oxazole-4-carboxylic acid ethyl ester 
• 591-50-4 iodobenzene 
• 92629-11-3 5-bromo-2-phenyl-1,3-oxazole 
• 3278-14-6 N-phenethylbenzamide 
• 460081-28-1 5-bromo-2-phenyl-oxazole-4-carboxylic acid ethyl ester 
• 92-71-7 2,5-diphenyloxazole 

Downstream Products

• 143031-97-4 Benzenesulfonyl-(2,5-diphenyl-oxazol-4-yl)-acetonitrile 
• 573-34-2 2,4,5-triphenyloxazole 
• 113923-95-8 2,5-diphenyl-4-vinyloxazole 

Relevant articles and documents

Enantioselective Olefin Hydrocyanation without Cyanide

The enantioselective hydrocyanation of olefins represents a conceptually straightforward approach to prepare enantiomerically enriched nitriles. These, in turn, comprise or are intermediates in the synthesis of many pharmaceuticals and their synthetic derivatives. Herein, we report a cyanide-free dual Pd/CuH-catalyzed protocol for the asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov hydrocyanation of terminal olefins in which oxazoles function as nitrile equivalents. After an initial hydroarylation process, the oxazole substructure was deconstructed using a [4 + 2]/retro-[4 + 2] sequence to afford the enantioenriched nitrile product under mild reaction conditions.

Solar photo-thermochemical syntheses of 4-bromo-2,5-substituted oxazoles from N-arylethylamides

Solar photo-thermochemical C(sp3)-H bromination, conducted efficiently in a specially designed reactor, was reported recently. In the present study, the more complex formation of 4-bromo-2,5-substituted oxazoles from N-arylethylamides using this approach was achieved. The one-pot syntheses were carried out with N-bromosuccinimide-dichloroethane over 6 h (10.00 am to 4.00 pm) on sunny days. The isolated yields were in the range 42-82%. Benzylic bromination, followed by O-C bond formation through intramolecular nucleophilic substitution, and a second benzylic bromination followed by HBr elimination, gave the oxazole ring. A third bromination of the ring yielded the final product. The feasibility of synthesizing thiazole derivatives using a similar approach was also demonstrated. During the course of the reactions, succinimide and HBr were co-generated in the aqueous phase. Treatment with NaBrO3 and additional acid returned the reagent in 57% isolated yield upon chilling. The overall methodology was greener as a result.

Polyarylated thiazoles via a combined halogen dance - Cross-coupling strategy

The application of the halogen dance reaction for the synthesis of starting materials for cross-coupling reactions is reported. The obtained compounds were then successfully applied, in sequential Stille and Suzuki-Miyaura cross-coupling reactions to obta

Ethyl 2-chlorooxazole-4-carboxylate: A versatile intermediate for the synthesis of substituted oxazoles

(formula presented) R1 = Ar, Het, alkenyl R2 = H, Ar, Het, alkenyl, alkynyl R3 = H, CO2H, Ar, Het, alkenyl, alkynyl By using a sequence of regiocontrolled halogenation and palladium-catalyzed coupling reactions,

Substituted Oxazoles: Synthesis via Lithio Intermediates

Reactions of 2-α-, 2-, 4-, and 5-lithiooxazoles are used to prepare various substituted derivatives.Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldhyde is described, and a rationale for this behavior is offered.Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with n-butyllithium.Deprotonation of the ortho position of the 2-phenyl group and addition of n-butyl to the 2-position of the oxazole compete with the desired 4-lithiation.The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-2,5-diphenyloxazole.This intermediate has been converted to the 4-bromo, -methyl, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivatives.Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position.Deprotonation of 2-alkyloxazoles occurs at the α-carbon in preference to ring sites.Further reaction of an α-phenyl-2-oxazolemethanol methoxymethyl ether with base and acetyl chloride leads to an acyloin derivative.Chromic acid oxidation is used to prepare both 2- and 4-benzoyloxazoles.The formation of an 2-ethoxyoxazole from 2-oxazolone vis Meerwein salt chemistry is described.