123066-64-8

Basic information

• Product Name: 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine
• Synonyms: 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine;4-(3,5-Bis(trifluoroMethyl)-1H-pyrazol-1-yl)aniline;CRAC intermediate 2;4-[3,5-bis(trifluoromethyl)pyrazol-1-yl]aniline
• CAS NO: 123066-64-8
• Molecular Formula: C₁₁H₇F₆N₃
• Molecular Weight: 295.1837992
• Mol File: 123066-64-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 140-142 °C
• Boiling Point: 298.4°C at 760 mmHg
• Flash Point: 134.3°C
• Appearance: /
• Density: 1.52 g/cm³
• Vapor Pressure: 0.00127mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.65±0.10(Predicted)
• CAS DataBase Reference: 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine(123066-64-8)
• EPA Substance Registry System: 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine(123066-64-8)

Safety Data

• Hazardous Substances Data: 123066-64-8(Hazardous Substances Data)

Usage

General Description

4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine is a chemical compound with the molecular formula C14H9F12N3. It is a phenylamine derivative containing a pyrazole ring and two trifluoromethyl groups. 4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)-phenylamine is often used in pharmaceutical research and development due to its potential biological activities and pharmacological properties. It has been studied for its potential applications in treating a variety of medical conditions, including cancer and inflammatory diseases. The presence of the trifluoromethyl groups in the molecule can enhance its bioavailability and metabolic stability, making it a promising candidate for further drug development.

InChI:InChI=1/C11H7F6N3/c12-10(13,14)8-5-9(11(15,16)17)20(19-8)7-3-1-6(18)2-4-7/h1-5H,18H2

Upstream product

• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 1694-30-0 1,1,1,5,5,5-hexafluoro-4-hydroxy-pent-3-en-2-one 
• 123066-63-7 1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole 
• 100-16-3 4-nitrophenylhydrazone 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 

Downstream Products

• 1101891-14-8 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-2,3,3-trichloroacrylamide 
• 1315322-99-6 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)-4-chlorobenzenesulfonamide 
• 1315323-00-2 N-(4-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)phenyl)-4-methylbenzenesulfonamide 
• 1431385-27-1 [(2,6-difiuorophenyl)methyl]-N-{4-[3,5-bis(trifluoromethyl)pyrazolyl]phenyl}amine 
• 1076689-99-0 2-methoxy-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl] nicotinanilide 
• 292610-93-6 4-methyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-nicotinanilide monohydrochloride 
• 1076692-18-6 2,4-dimethyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide monohydrochloride 
• 245745-97-5 2-chloro-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide 
• 1076689-98-9 4-trifluoromethyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide 
• 1076690-01-1 5-chloro-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide 
• 1026350-55-9 5-fluoro-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide 
• 1076690-00-0 5-methyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]nicotinanilide 
• 1076692-17-5 6-methyl-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl] nicotinanilide monohydrochloride 
• 1076689-97-8 4-chloro-4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-nicotinanilide 

Relevant articles and documents

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Microwave-assisted and continuous flow multistep synthesis of 4-(pyrazol-1-yl)carboxanilides

A series of 4-(pyrazol-1-yl)carboxanilides active as inhibitors of canonical transient receptor potential channels were synthesized in an efficient three-step protocol using controlled microwave heating. The general synthetic strategy involves condensation of 4-nitrophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by reduction of the nitro group to the amine, which is then amidated with carboxylic acids. Compared to the conventional protocol a dramatic reduction in overall processing time from ～2 days to a few minutes was achieved, accompanied by significantly improved product yields. In addition, the first two steps in the synthetic pathway were also performed under continuous flow conditions providing similar isolated product yields. As an alternative to the three-step protocol, a novel two-step route to the desired 4-(pyrazol-1-yl)carboxanilides was devised involving condensation of 4-bromophenylhydrazine with appropriate 1,3-dicarbonyl building blocks, followed by Pd-catalyzed Buchwald-Hartwig amidation with carboxylic acid amides.