1H-indazole-6-carboxylic acid

HCID 16227938

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Grundinformationen

CAS: 704-91-6
Standard-SMILES: O=C(O)c1ccc2cn[nH]c2c1
InChIKey: DNCVTVVLMRHJCJ-UHFFFAOYSA-N
Summenformel: C8H6N2O2
Durchschnittliche Molmasse: 162,15 g/mol
Monoisotopische Masse: 162,04292743

Namen und Bezeichner

Bevorzugter Name: 1H-indazole-6-carboxylic acid
IUPAC: 1H-indazole-6-carboxylic acid
Englischer Name: 1H-indazole-6-carboxylic acid
Summenformel: C8H6N2O2
Molmasse: 162.15

Namen und Synonyme

1H-Indazole-6-carboxylic acid704-91-6DTXSID30585471RefChem:238414DTXCID80536236676-984-61H-indazole-6-carboxylicacidMFCD06804571INDAZOLE-6-CARBOXYLIC ACID6-carboxyindazole2H-indazole-6-carboxylic acid6-indazolecarboxylic acid

Weitere Namen anzeigen

6-Carboxy-1H-indazole1H-Indazole-6-carboylic acid1H-Indazol-6-carboxylic acid1-H-indazole-6-carboxyle acid6-(1H)INDAZOLE CARBOXYLIC ACID1H-Indazole-6-carboxylic acid 97%1H-Indazole-6-carboxylic acid, 97%+

CHEMBL4867341SCHEMBL260992SCHEMBL25401469SCHEMBL29365815DNCVTVVLMRHJCJ-UHFFFAOYSA-NBDBM505781001H-Indazole-6-carboxylic acid, 97%AKOS000118108

Datenbank-Bezeichner

CAS: 704-91-6
PubChem CID: 16227938
DTXSID: DTXSID30585471
ChEMBL: CHEMBL4867341
EC Number: 676-984-6
Nikkaji: J3.352.558C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,8
Polarare Oberfläche (TPSA): 66 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 1
Schwere Atome: 12
Formalladung: 0
Komplexität: 195

Physikochemische Eigenschaften

Schmelzpunkt: 302 · 302-307 °C
Siedepunkt: 443.7 · 443.7±18.0 °C(Predicted)
Dichte: 1.506 · 1.506±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
pka: 4.01 · 4.01±0.30(Predicted)
Aggregatzustand: Crystalline Powder
Farbe: White to light brown
InChI: InChI=1S/C8H6N2O2/c11-8(12)5-1-2-6-4-9-10-7(6)3-5/h1-4H,(H,9,10)(H,11,12)
InChIKey: DNCVTVVLMRHJCJ-UHFFFAOYSA-N
SMILES: N1C2=C(C=CC(C(O)=O)=C2)C=N1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (16.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (16.7%)

Sicherheitsdaten

wgk: 3
hs_code: 29339980
hazard_class: IRRITANT
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen

Verwenden1H-Indazole-6-carboxylic Acid is used as a reagent to synthesize azabicyclic aryl amides, which act as α7 nicotinic acetylcholine receptor agonists.

Darstellung · 1 Eintrag

synthetischeSynthesis of 1H-indazole-6-carboxylic acid, H2L3: MeL3Ac (1.0 g; 4.6 mmol) was dissolved in 40 mL THF, and this solution was added to a 40 mL aqueous solution of lithium hydroxide (5.0 g; 210 mmol). The resulting suspension was heated at reflux with vigorous stirring overnight, after which time the solution was concentrated under vacuum to remove the organic phase. The resulting solution was filtered, adjusted to pH 3 with conc. HCl, to precipitate the product as a pale brown solid, which was filtered, washed with water and dried under vacuum. Yield 315 mg, 43%. mp 292–296 °C (decomp); δH (500 MHz, d6-DMSO): 7.67 (dd, 1H, J = 8.3, 1.0 Hz, H4 ), 7.85 (dd, 1H, J = 8.3, 0.8 Hz, H3 ), 8.15 (s, 1H, H6 ), 8.18 (d, 1H, J = 0.8 Hz, H2 ), 13.24 (br s, 2H, H1 & H5 ); δC (125 MHz, CD3OD): 114.1, 122.0, 122.6, 127.1, 130.6, 135.2, 141.4, 170.4; HRMS-ESI m/z: found: 163.0503; C8H7N2O2 requires: 163.0502 [M + H+ ]; ˉνmax/cm1 (KBr): 3258 br, 2864 br, 2582 br, 1679 s, 1579 m, 1518 m, 1425 m, 1230 s, 1087 m, 954 s, 857 m, 762 m, 693 m.