162758-35-2

Basic information

• Product Name: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid
• Synonyms: 5-(4-CHLORO-PHENYL)-1-(2,4-DICHLORO-PHENYL)-4-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID;RIMONABANT CARBOXYLIC ACID;5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHY-1H-PYRAZOLE-3-CARBOXYLIC ACID;RIMONABANTACID;5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid;1H-Pyrazole-3-carboxylic acid, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-;Rimonabant carboxylic acid ,99%
• CAS NO: 162758-35-2
• Molecular Formula: C₁₇H₁₁Cl₃N₂O₂
• Molecular Weight: 381.64
• Product Categories: pharmacetical
• Mol File: 162758-35-2.mol
• Article Data: 40

Chemical Properties

• Melting Point: 202-203 °C
• Boiling Point: 551.208 °C at 760 mmHg
• Flash Point: 287.161 °C
• Appearance: /
• Density: 1.48
• Vapor Pressure: 5.52E-13mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.33±0.34(Predicted)
• CAS DataBase Reference: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid(162758-35-2)
• EPA Substance Registry System: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid(162758-35-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 162758-35-2(Hazardous Substances Data)

Usage

Description

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid is a white fine solid powder that belongs to the class of pyrazole-carboxylic acids. It is a chemical compound with a specific molecular structure featuring a pyrazole ring and two chlorophenyl groups, which contribute to its unique properties and applications.

Uses

Used in Pharmaceutical Industry:
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid is used as a key intermediate in the synthesis of biarylpyrazole-based derivatives. These derivatives are known to act as cannabinoid CB1 receptor antagonists, which have potential applications in the development of antiobesity medications.
Specifically, this compound is identified as metabolite M9 of Rimonabant (R517800), an antiobesity agent. Rimonabant has been shown to help in weight management by targeting the endocannabinoid system, which is involved in regulating appetite and energy balance.

InChI:InChI=1/C17H11Cl3N2O2/c1-9-15(17(23)24)21-22(14-7-6-12(19)8-13(14)20)16(9)10-2-4-11(18)5-3-10/h2-8H,1H3,(H,23,24)

Upstream product

• 434952-87-1 (Z)-ethyl 2-[2-(2,4-dichlorophenyl)hydrazono]-4-(4-chlorophenyl)-3-methyl-4-oxobutanoate 
• 158941-22-1 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 
• 1012314-40-7 ethyl 4-(4-chlorophenyl)-3-methyl-4-oxydo-2-oxobuten-3-oate lithium salt 
• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 6285-05-8 4'-chloropropiophenone 
• 95-92-1 oxalic acid diethyl ester 
• 13123-92-7 (2,4-dichlorophenyl)hydrazine 
• 169544-41-6 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester 
• 170937-37-8 4-(4-chlorophenyl)-2-[(2,4-dichlorophenyl)-hydrazono]-3-methyl-4-oxobutyric acid ethyl ester 
• 944154-78-3 C₁₉H₁₈Cl₃N₂O₃^(1-)*Li⁽¹⁺⁾ 
• 192702-54-8 5-(4-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 
• 1193-72-2 1-bromo-2,4-dichlorobenzene 
• 68716-47-2 2,4-dichlorophenylboronic acid 
• 1030616-35-3 phenyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate 

Downstream Products

• 168273-05-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 
• 953758-69-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylpiperazin-1-yl)-1H-pyrazole-3-carboxamide 
• 1291067-90-7 O-4332 
• 1291067-91-8 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-[3-(N,N-diethylamino) propyl]-1H-pyrazol-3-carboxamide 
• 1291067-92-9 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-methylcyclohexyl)-1H-pyrazol-3-carboxamide 
• 1291067-93-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole-3-carboxamide 
• 1291067-94-1 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-(piperidin-1-yl)butyl)-1H-pyrazole-3-carboxamide 
• 1291067-95-2 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-[2-(7-methoxynaphthalen-2-yl)ethyl]-1H-pyrazol-3-carboxamide 
• 1627941-96-1 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627941-98-3 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-(pentafluoro-λ⁶-sulfanyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627942-00-0 N-(3-(tert-butyl)phenyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1627942-01-1 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627942-02-2 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-(pentafluoro-λ⁶-sulfanyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627942-03-3 N-(4-(tert-butyl)phenyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 

Relevant articles and documents

An improved synthesis of rimonabant: Anti-obesity drug

A novel, cost-effective, and efficient process was developed for the large-scale synthesis of Rimonabant 1, an anti-obesity drug. The process involves the conversion of 4-chloro propiophenone 2 to cyclized acid 6 as a key intermediate that afforded Rimonabant 1 in good yield.

Novel 1,5-diaryl pyrazole-3-carboxamides as selective COX-2/sEH inhibitors with analgesic, anti-inflammatory, and lower cardiotoxicity effects

COX-2 selective drugs have been withdrawn from the market due to cardiovascular side effects, just a few years after their discovery. As a result, a new series of 1,5-diaryl pyrazole carboxamides 19–31 was synthesized as selective COX-2/sEH inhibitors wit

Divalent cannabinoid-1 receptor ligands: A linker attachment point survey of SR141716A for development of high-affinity CB1R molecular probes

The cannabinoid-1 receptor (CB1R) inverse agonist SR141716A has proven useful for study of the endocannabinoid system, including development of divalent CB1R ligands possessing a second functional motif attached via a linker unit. These have predominantly employed the C3 position of the central pyrazole ring for linker attachment. Despite this precedent, a novel series of C3-linked CB1R-D2R divalent ligands exhibited extremely high affinity at the D2R, but only poor affinity for the CB1R. A systematic linker attachment point survey of the SR141716A pharmacophore was therefore undertaken, establishing the C5 position as the optimal site for linker conjugation. This linker attachment survey enabled the identification of a novel divalent ligand as a lead compound to inform ongoing development of high-affinity CB1R molecular probes.

SUBSTITUTED PYRAZOLE COMPOUNDS AS CB1 RECEPTOR ANTAGONISTS AND USES THEREOF

The present invention relates to compounds of formula 1, or isotopic forms, stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, polymorphs, prodrugs, S-oxides or N-oxides thereof, and processes for their preparation. The invention furth