73776-25-7

Basic information

• Product Name: 2-CHLORO-3-QUINOLINECARBOXYLIC ACID
• Synonyms: 2-CHLORO-QUINOLINE-3-CARBOXYLIC ACID;2-CHLORO-3-QUINOLINECARBOXYLIC ACID;IFLAB-BB F1973-0014;RARECHEM AL BE 0745;VITAS-BB TBB000076;3-Carboxy-2-chloroquinoline;2-Chloroquinoline-3-carboxylicacid95%;AKOS BBS-00007300
• CAS NO: 73776-25-7
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Product Categories: pharmacetical;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 73776-25-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: 199-240 °C
• Boiling Point: 363.8 °C at 760 mmHg
• Flash Point: 173.8 °C
• Appearance: /
• Density: 1.469 g/cm³
• Vapor Pressure: 6.24E-06mmHg at 25°C
• PKA: 2.06±0.30(Predicted)
• CAS DataBase Reference: 2-CHLORO-3-QUINOLINECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-3-QUINOLINECARBOXYLIC ACID(73776-25-7)
• EPA Substance Registry System: 2-CHLORO-3-QUINOLINECARBOXYLIC ACID(73776-25-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 73776-25-7(Hazardous Substances Data)

Usage

Uses

Useful quinolinecarboxylic acid for quinoline chemistry.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 2178, 1989 DOI: 10.1021/jm00129a026Journal of Heterocyclic Chemistry, 26, p. 1589, 1989

InChI:InChI=1/C10H6ClNO2/c11-9-7(10(13)14)5-6-3-1-2-4-8(6)12-9/h1-5H,(H,13,14)/p-1

Upstream product

• 2003-79-4 2-oxo-1,2-dihydro-quinoline-3-carboxylic acid 
• 612-62-4 2-Chloroquinoline 
• 108-20-3 di-isopropyl ether 
• 108-18-9 diisopropylamine 
• 1215476-61-1 C₂₀H₁₈ClN₃O 
• 103-84-4 Acetanilid 
• 62-53-3 aniline 
• 36926-82-6 2-oxo-1,2-dihydroquinoline-3-carbonitrile 
• 124-38-9 carbon dioxide 
• 862249-68-1 2-chloro-3-lithioquinoline 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 

Downstream Products

• 136812-19-6 2-chloroquinoline-3-carbonyl chloride 
• 1308339-08-3 (R)-(6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)(2-(2-fluorobenzyl)quinolin-3-yl)methanone 
• 1039880-02-8 C₁₇H₁₃NO₃ 
• 88284-17-7 C₁₆H₁₁NO₃ 
• 1621109-04-3 N-(3-sulfamoylphenyl)-2-(triazolo[4,5-b]pyridin-3-yloxy)quinoline-3-carboxamide 
• 1621108-31-3 5-(2-(2-chloro-4-fluorophenoxy)quinoline-3-carboxamido)picolinic acid 
• 1621108-34-6 4-(2-(2,4-difluorophenoxy)quinoline-3-carboxamido)benzoic acid 
• 1621109-01-0 methyl 4-(2-chloroquinoline-3-carboxamido)benzoate 
• 1621109-02-1 C₂₄H₁₆F₂N₂O₄ 
• 1621108-75-5 2-(4-fluoro-2-methoxy-phenoxy)-N-(3-sulfamoylphenyl)quinoline-3-carboxamide 
• 929569-13-1 1-(4-methoxybenzyl)pyrazolo[4',3':5,6]pyrano[2,3-b]quinolin-4(1H)-one 
• 929569-11-9 3-methyl-1-phenylpyrazolo[4',3':5,6]pyrano[2,3-b]quinolin-4(1H)-one 
• 929569-12-0 1-phenylpyrazolo[4',3':5,6]pyrano[2,3-b]quinolin-4(1H)-one 
• 16498-85-4 methyl 2-chloroquinoline-3-carboxylate 

Relevant articles and documents

Cytotoxic triterpenoid–safirinium conjugates target the endoplasmic reticulum

Safirinium P and Q fluorescence labels were synthesized and conjugated with spacered triterpenoic acids to access hybrid structures. While the parent safirinium compounds were not cytotoxic at all, many triterpenoid safirinium P and Q conjugates showed moderate cytotoxicity. An exception, however, was safirinium P derived compound 30 holding low EC50 = 5.4 μM (for A375 cells) to EC50 = 7.5 μM (for FaDu cells) as well as EC50 = 6.6 μM for non-malignant fibroblasts NIH 3T3. Fluorescence imaging showed that the safirinium core structures cannot enter the cells (not even after a prolonged incubation time of 24 h), while the conjugates (as exemplified for 30) are accumulating in the endoplasmic reticulum but not in the mitochondria. The development of safirinium–hybrids targeting the endoplasmic reticulum can be regarded as a promising strategy in the development of cytotoxic agents.

TBHP-promoted oxidative cyclization of o-alkynylquinoline aldehydes: Metal/additive-free domino synthesis of pyrano[4,3-b]quinolin-1-ones

TBHP-promoted domino synthesis of pyrano[4,3-b]quinolin-1-ones is described from o-alkynylquinoline aldehydes. The radical reaction proceeded without metal and additive via oxidation of aldehydic C-H bond into C-OH bond followed by intramolecular 6-endo-d

Friedel-Crafts Chemistry. Part 48. Concise Synthesis of Condensed Azaheterocyclic [1,8]naphthyridinones, Azepino-, Azocino-, and Azoninoquinoline Systems via Friedel-Crafts Ring Closures

Unprecedented construction of a novel series of quinoline heteropolycycles (tetracyclic keto-analogues of [1,8]naphthyridinones, azepino-, azocino-A nd azonino[2,3-b]quinolinones systems) 10a-i by Friedel-Crafts cycliacylation reactions is described. Starting heterocyclic acids precursors 3a-i were prepared from easily accessible 2-chloroquinoline-3-carbaldehyde 1 via a three different synthetic pathways. Acid-catalyzed ring closures of the resulting tosylated acids were achieved under the influence of both Br?nsted and Lewis acid catalysts. The present strategy enables a straightforward synthesis to fused tetracyclic quinolinone skeletons as demonstrated by concise and atom-economical syntheses.