574-92-5

Basic information

• Product Name: 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID
• Synonyms: BUTTPARK 21\09-48;4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID;4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ACID;AKOS BBS-00000363;4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylicaci;4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINE- CARBOXYLIC ACID, TECH., 85%;3-Carboxy-4-hydroxy-7-trifluoromethylquinoline.;4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid, HPLC 85%
• CAS NO: 574-92-5
• Molecular Formula: C₁₁H₆F₃NO₃
• Molecular Weight: 257.17
• EINECS: 209-377-8
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 574-92-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 259-260 °C (dec.)(lit.)
• Boiling Point: 354.7 °C at 760 mmHg
• Flash Point: 168.3 °C
• Appearance: /
• Density: 1.4646 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.52±0.30(Predicted)
• CAS DataBase Reference: 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID(574-92-5)
• EPA Substance Registry System: 4-HYDROXY-7-TRIFLUOROMETHYL-3-QUINOLINECARBOXYLIC ACID(574-92-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: VB2188000
• Hazardous Substances Data: 574-92-5(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE CRYSTALLINE POWDER

Uses

4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid was used in the preparation of (4-hydroxy-7-trifluoromethylquinolin-3-yl)formaldehyde.

InChI:InChI=1/C11H6F3NO3/c12-11(13,14)5-1-2-6-8(3-5)15-4-7(9(6)16)10(17)18/h1-4H,(H,15,16)(H,17,18)

Upstream product

• 391-02-6 4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 98-16-8 3-trifluoromethylaniline 
• 370-35-4 diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate 

Downstream Products

• 322-97-4 7-trifluoromethyl-quinolin-4-ol 
• 59197-90-9 4-Hydroxy-7-trifluormethyl-3-chinolincarbonsaeurechlorid 
• 1471178-15-0 1-(2,4-dichlorobenzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-21-8 1-(2,4-dichlorobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-17-2 1-(4-cyanobenzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 1471178-23-0 1-(4-cyanobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid 
• 346-55-4 4-chloro-7-trifluoromethyl quinoline 

Relevant articles and documents

Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives

Abstract: Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (1) exhibits a moderate cytotoxic activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line and a weak activity against the HCT-116 human colorectal carcinoma cell line. In order to enhance the cytotoxic activity of this compound, it was modified by changing the side-chain substituent and/or forming a new heterocyclic ring fused to the pyridine ring. Heating compound 1 with chloroacetyl chloride gave a mixture of two isomeric O-acylation products ethyl 4-(2-chloroacetoxy)-7-(trifluoromethyl)-quinoline-3-carboxylate and 3-chloro-8-(trifluoromethyl)-2H-pyrano[3,2-c]quinoline-2,4(3H)-dione, whereas the reaction with acetyl chloride in NaOH formed an N-acylation product 1-acetyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid. The reactions of compound 1 with urea, thiourea, hydrazine hydrate, hydroxylamine, o-phenylenediamine, phenyl isothiocyanate, and ethyl acetoacetate yielded the corresponding condensation products 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]urea, 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]thiourea, 7-(trifluoromethyl)-1,2-dihydropyrazolo[4,3-c]quinolin-3-one, 7-(trifluoromethyl)isoxazolo[4,5-c]quinolin-3(2H)-one, 3-(trifluoromethyl)-13H-benzo[2,3][1,4]diazepino[6,5-c]quinolin-7-ol, 3-phenyl-2-thioxo-8-(trifluoromethyl)-2,3-dihydro-4H-[1,3]oxazino[5,6-c]quinolin-4-one and ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4H-pyrano[3,2-c]quinolone 3-carboxylate, respectively. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data.

Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof

Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.