| Identification | More | [Name]
2-CHLORO-3-QUINOLINECARBOXYLIC ACID | [CAS]
73776-25-7 | [Synonyms]
2-CHLORO-3-QUINOLINECARBOXYLIC ACID
2-CHLORO-QUINOLINE-3-CARBOXYLIC ACID
AKOS BBS-00007300
IFLAB-BB F1973-0014
RARECHEM AL BE 0745
VITAS-BB TBB000076 | [Molecular Formula]
C10H6ClNO2 | [MDL Number]
MFCD03030039 | [Molecular Weight]
207.61 | [MOL File]
73776-25-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
199-240 °C | [Boiling point ]
363.8±27.0 °C(Predicted) | [density ]
1.469±0.06 g/cm3(Predicted) | [storage temp. ]
Store at room temperature | [form ]
solid | [pka]
2.06±0.30(Predicted) | [color ]
Grey | [InChI]
InChI=1S/C10H6ClNO2/c11-9-7(10(13)14)5-6-3-1-2-4-8(6)12-9/h1-5H,(H,13,14) | [InChIKey]
XFSORZYTTCOBFN-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C=C(C(O)=O)C=1Cl | [CAS DataBase Reference]
73776-25-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
2933491090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Useful quinolinecarboxylic acid for quinoline chemistry. | [Synthesis Reference(s)]
Journal of Medicinal Chemistry, 32, p. 2178, 1989 DOI: 10.1021/jm00129a026
Journal of Heterocyclic Chemistry, 26, p. 1589, 1989 | [Synthesis]
General procedure for the synthesis of 2-chloro-3-quinolinecarboxylic acid from 2-chloro-3-quinolinecarboxaldehyde: General method: a mixed solution of 2-chloro-3-quinolinecarboxaldehyde (0.5 mmol), tert-butylhydrogen peroxide (TBHP, 4.0 eq.), and dichloroethane (DCE, 2.0 mL) was placed under aerobic environment and heated at 80°C for 6 to 8 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the reaction mixture and extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with water and saturated saline and subsequently dried over anhydrous sodium sulfate (Na2SO4). The organic solvent was removed by concentration under reduced pressure, and the resulting crude product was purified by column chromatography (eluent ratio: hexane:ethyl acetate=15:5) to afford the target product 2-chloro-3-quinolinecarboxylic acid. | [References]
[1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1019 - 1022
[2] Green Chemistry, 2012, vol. 14, # 6, p. 1649 - 1656
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10329 - 10342
[4] Australian Journal of Chemistry, 2017, vol. 70, # 10, p. 1082 - 1092
[5] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1339 - 1340 |
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