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Indazole-3-carboxylic acid

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Name

Indazole-3-carboxylic acid

EINECS 224-794-5
CAS No. 4498-67-3 Density 1.506 g/cm3
PSA 65.98000 LogP 1.26110
Solubility N/A Melting Point 266-268 °C
Formula C8H6N2O2 Boiling Point 443.7 °C at 760 mmHg
Molecular Weight 162.148 Flash Point 222.2 °C
Transport Information N/A Appearance yellow crystal
Safety 26-36/37/39-22 Risk Codes 22-36-36/37/38
Molecular Structure Molecular Structure of 4498-67-3 (Indazole-3-carboxylic acid) Hazard Symbols IrritantXi, HarmfulXn
Synonyms

Indazole-3-carboxylicacid (7CI);3(1H)-Indazolecarboxylic acid;3-Carboxy-1H-indazole;3-Carboxyindazole;NSC 520610;1H-indazole-3-carboxylic acid;1H-Indazole-3-carboxylicacid;

Article Data 27

Indazole-3-carboxylic acid Synthetic route

91-56-5

indole-2,3-dione

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydroxide In water at 20 - 50℃; for 1.5h;
Stage #2: With sulfuric acid; sodium nitrite In water at 0℃; for 1h;
Stage #3: With hydrogenchloride; tin(ll) chloride In water for 1.16667h;
100%
With sodium hydroxide; sulfuric acid; sulfur dioxide; sodium nitrite Reagens 4: Zinnchloruer;
With sulfuric acid; sodium nitrite danach SnCl2;
186966-06-3

methyl 1-acetylindazole-3-carboxylate

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In hydrogenchloride; water100%
With sodium hydroxide; water for 1.5h; Heating;97%
78155-12-1

ethyl 1-acetyl-1H-indazole-3-carboxylate

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; water for 1.5h; Heating;98%
186966-03-0

1-(3-(morpholine-4-carbonyl)-1H-indazol-1-yl)ethanone

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; water for 3h; Heating;96%
1630015-70-1

4-bromobenzylideneaminoisatine

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-bromobenzylideneaminoisatine With hydrogenchloride In water; acetic acid at 90 - 100℃; for 1h;
Stage #2: With acetic acid at 115℃; for 1h;
85%
10604-20-3

1-(benzylideneamino)indoline-2,3-dione

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In dichloromethane; ISOPROPYLAMIDE; water at 15 - 90℃; Product distribution / selectivity; Reflux; Inert atmosphere;76%
Stage #1: 1-(benzylideneamino)indoline-2,3-dione With hydrogenchloride; acetic acid In water at 90℃; for 1h;
Stage #2: With acetic acid at 115℃; for 0.5h;
71%
64132-13-4

3-(hydroxymethyl)-1H-indazole

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With chromium(VI) oxide; sulfuric acid In acetone at 20℃; for 24h;64%
With chromium(VI) oxide; sulfuric acid In acetone at 20℃; for 24h;64%

tin(II)chloride dihydrate

91-56-5

indole-2,3-dione

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid; sodium nitrite In hydrogenchloride; water31%
861798-91-6

1-dimethylamino-indolin-2-one

871876-73-2

2,3-dimethyl-4-nitroso-aniline

141-52-6

sodium ethanolate

4498-67-3

1H-Indazole-3-carboxylic acid

10604-20-3

1-benzylideneamino-indole-2,3-dione

64-19-7

acetic acid

A

100-52-7

benzaldehyde

B

4498-67-3

1H-Indazole-3-carboxylic acid

Conditions
ConditionsYield
mit Wasserdampf;

Indazole-3-carboxylic acid Specification

With the CAS registry number 4498-67-3, the IUPAC name of Indazole-3-carboxylic acid is 1H-indazole-3-carboxylic acid. The product's categories are Pharmaceutical Intermediates; Acids and Derivatives; Heterocycles; Indoles and Derivatives; Pharmacetical; Carboxylic Acids; Organic Acids; Indazoles; Indole Derivatives; Carboxylic Acids; Fused Ring Systems; Building Blocks; Heterocyclic Building Blocks. It is yellow crystal which is stable under normal temperature and pressure. Additioanlly, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1).ACD/LogP: 1.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.38; (4)ACD/LogD (pH 7.4): -1.57; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.06; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.743; (13)Molar Refractivity: 43.54 cm3; (14)Molar Volume: 107.6 cm3; (15)Polarizability: 17.26×10-24 cm3; (16)Surface Tension: 85.2 dyne/cm; (17)Enthalpy of Vaporization: 73.93 kJ/mol; (18)Vapour Pressure: 1.18E-08 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 4; (21)Exact Mass: 162.042927; (22)MonoIsotopic Mass: 162.042927; (23)Topological Polar Surface Area: 66; (24)Heavy Atom Count: 12; (25)Complexity: 196.

Preparation of Indazole-3-carboxylic acid: It can be obtained by 1-acetyl-1H-indazole-3-carboxylic acid ethyl ester. This reaction needs reagents NaOH and water by heating. The reaction time is 1.5 hours. The yield is 98%.

Uses of Indazole-3-carboxylic acid: It is used in organic synthesis. For example: it can react with 1,4-dimethyl-[1,4]diazepan-6-ylamine to get 1H-indazole-3-carboxylic acid (1,4-dimethyl-[1,4]diazepan-6-yl)-amide. This reaction needs reagent 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride and solvent CH2Cl2 at ambient temperature. The reaction time is 5 hours. The yield is 21%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(O)c2nnc1ccccc12
2. InChI:InChI=1/C8H6N2O2/c11-8(12)7-5-3-1-2-4-6(5)9-10-7/h1-4H,(H,9,10)(H,11,12) 
3. InChIKey:BHXVYTQDWMQVBI-UHFFFAOYAD

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