| Identification | More | [Name]
Indazole-3-carboxylic acid | [CAS]
4498-67-3 | [Synonyms]
1H-INDAZOL-3-CARBONIC ACID
1H-INDAZOLE-3-CARBONIC ACID
1H-INDAZOLE-3-CARBOXYLIC ACID
3-CARBOXYINDAZOLE
3-INDAZOLECARBOXYLIC ACID
AKOS BB-9978
INDAZOLE-3-CARBOXYLIC ACID
3-Carboxy-1H-indazole
INDAPAMIDE
3(1H)-Indazolecarboxylic Acid
NSC 520610
Indazole-3-carboxylic acid ,98% | [EINECS(EC#)]
224-794-5 | [Molecular Formula]
C8H6N2O2 | [MDL Number]
MFCD00211066 | [Molecular Weight]
162.15 | [MOL File]
4498-67-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystal | [Melting point ]
266-270 °C (dec.) | [Boiling point ]
443.7±18.0 °C(Predicted) | [density ]
1.506±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
powder
| [pka]
3.03±0.10(Predicted) | [color ]
beige
| [Usage]
Indole derivatives useful in treatment of pain and inflammation | [Detection Methods]
HPLC,NMR | [BRN ]
6354 | [InChI]
InChI=1S/C8H6N2O2/c11-8(12)7-5-3-1-2-4-6(5)9-10-7/h1-4H,(H,9,10)(H,11,12) | [InChIKey]
BHXVYTQDWMQVBI-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2)C(C(O)=O)=N1 | [CAS DataBase Reference]
4498-67-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H319 | [Precautionary statements ]
P264-P270-P280-P301+P312-P305+P351+P338-P337+P313 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [REACH Registrations]
Inactive | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystal | [Uses]
Indazole-3-carboxylic acid is indole derivatives useful in treatment of pain and inflammation
| [Application]
Indazole-3-carboxylic acid is a key synthetic intermediate for the preparation of various indazole derivatives. Its ester derivatives can react with hydrazine hydrate to form acylhydrazines, which in turn react with aldehydes and ketones to form hydrazones. It can act as a ligand to form coordination compounds with biochemical properties [1]. Furthermore, it can replace the traditional indazole-3-carboxylic acid methyl ester as a direct starting material for the synthesis of synthetic cannabinoids (SCs) and their metabolites [2]. | [Preparation]
Indazole-3-carboxylic acids are prepared from the corresponding isatins via the von Auwers method[3]. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 26, p. 531, 1989 DOI: 10.1002/jhet.5570260251 | [References]
[1] García-Valdivia, A. A., Jannus, F., García-García, A., Choquesillo-Lazarte, D., Fernández, B., Medina-O’donnell, M., Lupiáñez, J. A., Cepeda, J., Reyes-Zurita, F. J., & Rodríguez-Diéguez, A. (2021). Anti-cancer and anti-inflammatory activities of a new family of coordination compounds based on divalent transition metal ions and indazole-3-carboxylic acid. Journal of Inorganic Biochemistry, 215, Article 111308. https://doi.org/10.1016/j.jinorgbio.2020.111308
[2] Rautio, T., Connolly, M. J., Liu, H., Konradsson, P., Gréen, H., Dahlén, J., & Wu, X. (2024). Direct and selective alkylation of indazole-3-carboxylic acid for the preparation of synthetic cannabinoids and metabolites. Forensic Chemistry, 40, Article 100603. https://doi.org/10.1016/j.forc.2024.100603
[3] Buu-Hoi, N. P., Hoeffinger, J. P., & Jacquignon, P. (1964). Indazole-3-carboxylic acids and their derivatives. Journal of Heterocyclic Chemistry, 1 5, 239–241. https://doi.org/10.1002/jhet.5570010505
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