142818-03-9

Basic information

• Product Name: 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID
• Synonyms: 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID;1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID;TIMTEC-BB SBB001236;1-(4-Nitrophenyl)-5-(trifluoromethyl)pyrazole-4-carboxylic acid 97%;1-(4-Nitrophenyl)-5-(trifluoromethyl)pyrazole-4-carboxylicacid97%;1-(4-Nitrophenyl)-5-(trifluoromethyl)pyrazole-;BUTTPARK 33\06-15
• CAS NO: 142818-03-9
• Molecular Formula: C₁₁H₆F₃N₃O₄
• Molecular Weight: 301.18
• EINECS: 238-178-9
• Product Categories: Carboxylic Acids;Pyrazoles & Triazoles;Carboxylic Acids;Pyrazoles & Triazoles;Building Blocks;Heterocyclic Building Blocks;Pyrazoles
• Mol File: 142818-03-9.mol

Chemical Properties

• Melting Point: 199-203 °C
• Boiling Point: 452.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.65±0.1 g/cm3(Predicted)
• PKA: 2.61±0.36(Predicted)
• CAS DataBase Reference: 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID(142818-03-9)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID(142818-03-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 142818-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, potentially offering novel therapeutic options for a range of medical conditions.
Used in Pesticide Industry:
In the pesticide industry, 1-(4-NITROPHENYL)-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLIC ACID is used as a building block for the creation of new pesticides. Its chemical properties may contribute to the effectiveness of these products in controlling pests and protecting crops, while also potentially reducing the environmental impact of traditional pesticides.

InChI:InChI:1S/C11H6F3N3O4/c12-11(13,14)9-8(10(18)19)5-15-16(9)6-1-3-7(4-2-6)17(20)21/h1-5H,(H,18,19)

Upstream product

• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 571-55-1 ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate 
• 175137-35-6 ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate 
• 100-16-3 4-nitrophenylhydrazone 
• 142809-85-6 4-trifluoroacetyl-5-trifluoromethyl-1-(p-nitrophenyl)pyrazole 

Relevant articles and documents

Discovery of a Highly Selective and Potent TRPC3 Inhibitor with High Metabolic Stability and Low Toxicity

The overactivation of transient receptor potential canonical 3 (TRPC3) is associated with neurodegenerative diseases and hypertension. Pyrazole 3 (Pyr3) is reported as the most selective TRPC3 inhibitor, but it has two inherent structural limitations: (1) the labile ester moiety leads to its rapid hydrolysis to the inactive Pyr8 in vivo, and (2) the alkylating trichloroacrylic amide moiety is known to be toxic. To circumvent these limitations, we designed a series of conformationally restricted Pyr3 analogues and reported that compound 20 maintains high potency and selectivity for human TRPC3 over its closely related TRP channels. It has significantly improved metabolic stability compared with Pyr3 and has a good safety profile. Preliminary evaluation of 20 demonstrated its ability to rescue Aβ-induced neuron damage with similar potency to that of Pyr3 in vitro. Collectively, these results suggest that 20 represents a promising scaffold to potentially ameliorate the symptoms associated with TRPC3-mediated neurological and cardiovascular disorders.

FACILE SYNTHETIC METHODS FOR 3- AND 5-TRIFLUOROMETHYL-4-TRIFLUOROACETYLPYRAZOLES AND THEIR CONVERSION INTO PYRAZOLE-4-CARBOXYLIC ACIDS

3- and 5-Trifluoromethyl-4-trifluoroacetylpyrazoles (4 and 5) were easily synthesized in excellent yields by reaction of β,β-bis(trifluoroacetyl)vinyl ethers 1, sulfides 2, and -amines 3 with hydrazines.Hydrolysis of these compounds (4 and 5) with aqueous potassium hydroxide gave the corresponding pyrazole-4-carboxylic acids (6 and 7) in high yields.