160842-62-6

Basic information

• Product Name: 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE
• Synonyms: BUTTPARK 43\57-64;3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE;3-(TERT-BUTYL)-1-METHYLPYRAZOLE-5-CARBONYL CHLORIDE;TIMTEC-BB SBB005464;1H-Pyrazole-5-carbonyl chloride, 3-(1,1-dimethylethyl)-1-methyl- (9CI);3-(tert-Butyl)-1-methylpyrazole-5-carbonyl;3-(tert-Butyl)-5-(chlorocarbonyl)-1-methyl-1H-pyrazole, 3-(tert-Butyl)-5-(chloroformyl)-1-methyl-1H-pyrazole;5-tert-butyl-2-methylpyrazole-3-carbonyl chloride
• CAS NO: 160842-62-6
• Molecular Formula: C₉H₁₃ClN₂O
• Molecular Weight: 200.67
• Product Categories: ACIDHALIDE
• Mol File: 160842-62-6.mol

Chemical Properties

• Boiling Point: 117 °C
• Flash Point: 121.1°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.00474mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.38±0.10(Predicted)
• CAS DataBase Reference: 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE(160842-62-6)
• EPA Substance Registry System: 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE(160842-62-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• Hazardous Substances Data: 160842-62-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE is used as a reactive intermediate for the synthesis of pharmaceuticals, leveraging its carbonyl chloride functionality to facilitate acylation and amidation reactions in the development of new drug molecules.
Used in Organic Chemistry:
In the field of organic chemistry, 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE is utilized as a building block in the preparation of heterocyclic compounds, contributing to the diversity and complexity of organic synthesis.
Used in Agrochemical Production:
3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE is employed in the production of agrochemicals, where its reactivity aids in the creation of compounds designed to protect crops and enhance agricultural productivity.
Used in Fine Chemicals Industry:
3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE is also used in the synthesis of fine chemicals, where its unique properties are harnessed to produce specialty chemicals for various applications, including but not limited to fragrances, dyes, and other high-value products.

InChI:InChI=1/C9H13ClN2O/c1-9(2,3)7-5-6(8(10)13)12(4)11-7/h5H,1-4H3

Upstream product

• 175277-11-9 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylic acid 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 133261-10-6 5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester 
• 13395-36-3 ethyl trimethylacetopyruvate 

Downstream Products

• 194290-01-2 3-[(5-tert-Butyl-2-methyl-2H-pyrazole-3-carbonyl)-amino]-benzoic acid ethyl ester 

Relevant articles and documents

From Lead to Drug Candidate: Optimization of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as Agents for the Treatment of Triple Negative Breast Cancer

Herein we report the sophisticated process of structural optimization toward a previously disclosed Src inhibitor, compound 1, which showed high potency in the treatment of triple negative breast cancer (TNBC) both in vitro and in vivo but had considerable toxicity. A series of 3-(phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives were synthesized. In vitro cell-based phenotypic screening together with in vivo assays and structure-activity relationship (SAR) studies finally led to the discovery of N-(3-((4-amino-1-(trans-4-hydroxycyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)ethynyl)-4-methylphenyl)-4-methyl-3-(trifluoromethyl)benzamide (13an). 13an is a multikinase inhibitor, which potently inhibited Src (IC50 = 0.003 μM), KDR (IC50 = 0.032 μM), and several kinases involved in the MAPK signal transduction. This compound showed potent anti-TNBC activities both in vitro and in vivo, and good pharmacokinetic properties and low toxicity. Mechanisms of action of anti-TNBC were also investigated. Collectively, the data obtained in this study indicate that 13an could be a promising drug candidate for the treatment of TNBC and hence merits further studies.

Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides

The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.