1H-indazole-6-carboxylic acid

Product Name: 1H-indazole-6-carboxylic acid
CAS No.: 704-91-6
Chemical Name: 1H-indazole-6-carboxylic acid
Synonyms: 6-Carboxy-1H-indazole;INDAZOLE-6-CARBOXYLIC ACID;1H-Indazole-6-carboylic acid;1H-Indazol-6-carboxylic acid;1-H-indazole-6-carboxyle acid;1H-INDAZOLE-6-CARBOXYLIC ACID;6-(1H)INDAZOLE CARBOXYLIC ACID;1H-Indazole-6-carboxylic acid 97%;1H-Indazole-6-carboxylic acid, 97%+;1H-Indazole-6-carboxylic acid
CBNumber: CB3113514
Molecular Formula: C8H6N2O2
Formula Weight: 162.15
MOL File: 704-91-6.mol

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1H-indazole-6-carboxylic acid Property

Melting point:: 302-307 °C
Boiling point:: 443.7±18.0 °C(Predicted)
Density: 1.506±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
pka: 4.01±0.30(Predicted)
form: Crystalline Powder
color: 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

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Safety

WGK Germany: 3
HazardClass: IRRITANT
HS Code: 29339980

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 702420
Product name: 1H-Indazole-6-carboxylic acid
Purity: 97%
Packaging: 1g
Price: $110
Updated: 2023/06/20

TRC

Product number: I509000
Product name: 1H-Indazole-6-carboxylic acid
Packaging: 1g
Price: $120
Updated: 2021/12/16

Matrix Scientific

Product number: 053791
Product name: 1H-Indazole-6-carboxylic acid
Packaging: 1g
Price: $19
Updated: 2021/12/16

Apolloscientific

Product number: OR60063
Product name: 1H-Indazole-6-carboxylic acid
Purity: 95%
Packaging: 1g
Price: $22
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4H21-1-D0
Product name: 1H-Indazole-6-carboxylic acid
Purity: 95%
Packaging: 1g
Price: $24
Updated: 2021/12/16

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1H-indazole-6-carboxylic acid Chemical Properties,Usage,Production

Uses

1H-Indazole-6-carboxylic Acid is used as a reagent to synthesize azabicyclic aryl amides, which act as α7 nicotinic acetylcholine receptor agonists.

Preparation

Synthesis 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/cm?1 (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.

Synthesis

170487-40-8

704-91-6

General procedure for the synthesis of 1H-indazole-6-carboxylic acid from methyl 1H-indazole-6-carboxylate: to a stirred solution of methyl 1H-indazole-6-carboxylate (1.0 g, 5.676 mmol, 1 eq.) in a solvent mixture of tetrahydrofuran/ethanol/water (1:1:1, 10 mL) was added lithium hydroxide (476 mg, 11.353 mmol, 2 eq.) . The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was diluted with 10 mL of water and the pH was adjusted to 4-5 with 2N hydrochloric acid to give a solid precipitate. The precipitate was collected by filtration and dried to give 1H-indazole-6-carboxylic acid (900 mg, 97% yield) as an off-white solid.TLC conditions: methanol/dichloromethane (1:9), Rf value 0.1.1H NMR (300 MHz, DMSO-d6): δ 13.36 (s, 1H), 13.04 (s, 1H), 8.24-8.08 (m , 2H), 7.85 (dd, J=8.5,0.9Hz, 1H), 7.67 (dd, J=8.4,1.3Hz, 1H).

References

[1] Patent: WO2016/8590, 2016, A1. Location in patent: Page/Page column 56
[2] Patent: WO2005/44817, 2005, A1. Location in patent: Page/Page column 118-119
[3] Patent: CN105693520, 2016, A. Location in patent: Paragraph 0196; 0197; 0198; 0199; 0200; 0201
[4] Patent: EP3067351, 2016, A1. Location in patent: Paragraph 0087; 0088

1H-indazole-6-carboxylic acid Preparation Products And Raw materials

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1H-indazole-6-carboxylic acid Suppliers

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View Lastest Price from 1H-indazole-6-carboxylic acid manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: 1H-Indazole-6-carboxylic acid 704-91-6
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

Career Henan Chemical Co

Product: 1H-INDAZOLE-6-CARBOXYLIC ACID 704-91-6
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 150KG
Release date: 2019-07-09

704-91-6, 1H-indazole-6-carboxylic acidRelated Search:

Methyl 1H-indazole-6-carboxylate 1H-indazole-6-carboxylic acid INDAZOLE-3-CARBOXYLIC ACID Indazole-3-carboxylic acid 5-Benzyloxy-1H-indazole-3-carboxylic acid 1H-INDAZOLE-4-CARBOXYLIC ACID 1H-INDAZOLE-7-CARBOXYLIC ACID, 3-BROMO- 1H-Indazole-3-carboxylic acid, 6-bromo- 5-Fluoro-3-indazolecarboxylic acid 5-Nitroindazole-3-carboxylic acid 1H-INDAZOLE-3-CARBOXYLIC ACID ETHYL ESTER 5-Methoxy-3-indazolecarboxylic acid 5-Amino-1H-indazole-3-carboxylic acid methyl ester,1H-Indazole-3-carboxylic acid, 5-amino-, methyl ester METHYL 5-METHOXY-1H-INDAZOLE-3-CARBOXYLATE 5-TRIFLUOROMETHOXY-1H-INDAZOLE-3-CARBOXYLIC ACID 7-CHLORO-1H-INDAZOLE-3-CARBOXYLIC ACID 5-CHLORO-1H-INDAZOLE-3-CARBOXYLIC ACID INDAZOLE-5-CARBOXYLIC ACID METHYL ESTER

INDAZOLE-6-CARBOXYLIC ACID

1H-INDAZOLE-6-CARBOXYLIC ACID

6-(1H)INDAZOLE CARBOXYLIC ACID

1H-Indazole-6-carboxylic acid 97%

1H-Indazole-6-carboxylic acid, 97%+

6-Carboxy-1H-indazole

1-H-indazole-6-carboxyle acid

1H-Indazol-6-carboxylic acid

1H-Indazole-6-carboylic acid

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1<i>H</i>-Indazole-6-carboxylic acid

704-91-6

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