Indazole-3-carboxylic acid supplier

Name
Indazole-3-carboxylic acid
EINECS 224-794-5
CAS No. 4498-67-3
Article Data27
CAS DataBase
Density 1.506 g/cm³
Solubility
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
Appearance yellow crystal
Safety 26-36/37/39-22
Risk Codes 22-36-36/37/38
Molecular Structure
Hazard Symbols Xi, Xn
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;
PSA 65.98000
LogP 1.26110

Synthetic route

: 91-56-5
indole-2,3-dione

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In hydrogenchloride; water	100%
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide; water for 3h; Heating;	96%

: 1630015-70-1
4-bromobenzylideneaminoisatine

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide; sulfuric acid; sodium nitrite In hydrogenchloride; water	31%

: 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

...Expand

: 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

Conditions	Yield
mit Wasserdampf;

...Expand

: 50264-88-5
indazole-3-carbonitrile

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 123704-99-4
N-acetylaminoisatin

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid for 2.5h; Heating;

: 7664-93-9
sulfuric acid

: 1-acetylamino-indoline-2,3-dione-3-oxime

: 4498-67-3
1H-Indazole-3-carboxylic acid

N-acetylamino-isatin-β oxime: N-acetylamino-isatin-β oxime

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid

N-benzylidenamino-isatin: N-benzylidenamino-isatin

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 7647-01-0
hydrogenchloride

: 10604-20-3
1-benzylideneamino-indole-2,3-dione

A: 100-52-7
benzaldehyde

B: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
mit Wasserdampf;

...Expand

: 109411-83-8
oxalic acid-(benzylidene-phenyl-hydrazide)-chloride

A: 4498-67-3
1H-Indazole-3-carboxylic acid

B N-benzylidenamino-isatin: N-benzylidenamino-isatin

Conditions

Conditions	Yield
With carbon disulfide; aluminium trichloride

: 3740-52-1
2-(2-nitrophenyl)acetic acid

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / cc. H2SO4 / 4 h / Heating 2: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 4: 97 percent / NaOH, water / 1.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 94 percent / cc. H2SO4 / 4 h / Heating 2: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 98 percent / NaOH, water / 1.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 89 percent / SOCl2 / dimethylformamide; 1,2-dichloro-ethane / 35-40 deg C, 2 h then 20 deg C, 2 h 2: 95 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 3: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 96 percent / NaOH, water / 3 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 89 percent / SOCl2 / dimethylformamide; 1,2-dichloro-ethane / 35-40 deg C, 2 h then 20 deg C, 2 h 2: 92 percent / Fe, aq. NH4Cl / propan-2-ol / 1 h / Heating 3: toluene / rt to 95 deg C 4: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 5: 96 percent / NaOH, water / 3 h / Heating View Scheme

: 30095-98-8
methyl (2-nitrophenyl)acetate

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 3: 97 percent / NaOH, water / 1.5 h / Heating View Scheme

: 31912-02-4
ethyl 2-nitrophenylacetate

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 98 percent / NaOH, water / 1.5 h / Heating View Scheme

: 186966-08-5
(2-acetylamino-phenyl)-acetic acid ethyl ester

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 2: 98 percent / NaOH, water / 1.5 h / Heating View Scheme

: 134810-89-2
methyl 3-(2-acetamidophenyl)propanoate

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / 90percent t-BuONO / acetic acid / 0.5 h / 90 - 95 °C 2: 97 percent / NaOH, water / 1.5 h / Heating View Scheme

: 25888-16-8
4-[(2-nitro-phenyl)-acetyl]-morpholine

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / H2 / 5percent Pd/C / toluene / Ambient temperature 2: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 96 percent / NaOH, water / 3 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 92 percent / Fe, aq. NH4Cl / propan-2-ol / 1 h / Heating 2: toluene / rt to 95 deg C 3: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 4: 96 percent / NaOH, water / 3 h / Heating View Scheme

: 80798-83-0
4-(2-aminophenylacetyl)morpholine

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / rt to 95 deg C 2: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 3: 96 percent / NaOH, water / 3 h / Heating View Scheme

: 186966-07-4
N-[2-(2-Morpholin-4-yl-2-oxo-ethyl)-phenyl]-acetamide

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / 90percent t-BuONO / toluene / 0.5 h / 90 - 95 °C 2: 96 percent / NaOH, water / 3 h / Heating View Scheme

: 123704-98-3
N-Acetylaminoisonitrosoacetanilide

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96percent H2SO4 / 0.25 h / 85 °C 2: aq. H2SO4 / 2.5 h / Heating View Scheme

: 114-83-0
1-acetyl-2-phenylhydrazine

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / hydroxylamine hydrochloride, sodium sulphate, 1 N HCl / H2O / 0.17 h / 100 °C 2: 96percent H2SO4 / 0.25 h / 85 °C 3: aq. H2SO4 / 2.5 h / Heating View Scheme

: 610-66-2
2-nitro-benzeneacetonitrile

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tin; hydrochloric acid 2: acid; sodium nitrite 3: concentrated hydrochloric acid View Scheme

: 2973-50-4
2-aminophenylacetonitrile

: 4498-67-3
1H-Indazole-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acid; sodium nitrite 2: concentrated hydrochloric acid View Scheme

: 106-49-0
p-toluidine

: 4498-67-3
1H-Indazole-3-carboxylic acid

: N-(p-tolyl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	66%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 619-45-4
4-methoxycarbonyl aniline

: methyl 4-(1H-indazole-3-carboxamido)benzoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	10%

: 106-47-8
4-chloro-aniline

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 23707-00-8
N-(4-chlorophenyl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	100%

: 67-56-1
methanol

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 43120-28-1
methyl 1H-indazole-3-carboxylate

Conditions

Conditions	Yield
With sulfuric acid for 2h; Heating;	98%
With sulfuric acid for 2h; Reflux;	95%
With thionyl chloride for 3h; Reflux;	95%

: 881693-01-2
5,6-diamino-1-ethyl-3,3-dimethylindol-2-one

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 5-ethyl-2-(1H-indazol-3-yl)-7,7-dimethyl-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one

Conditions

Conditions	Yield
Stage #1: 5,6-diamino-1-ethyl-3,3-dimethylindol-2-one; 1H-Indazole-3-carboxylic acid With PPA; phosphorus pentoxide at 150℃; for 6h; Stage #2: With ammonia In water pH=7 - 8;	97%

: 76272-41-8, 141650-55-7, 76272-56-5
endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 107007-95-4
endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃;	73%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 77-78-1
dimethyl sulfate

: 43120-28-1
methyl 1H-indazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In acetone for 4h; Reflux;	95%

: 2579-22-8
Phenylpropargyl aldehyde

: 88333-03-3, 10340-91-7
Benzyl isocyanide

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 106-40-1
4-bromo-aniline

: N,4-dibenzyl-2-(4-bromophenyl)-1-oxo-1,2-dihydropyrazino[1,2-b]indazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: Phenylpropargyl aldehyde; 4-bromo-aniline In 2,2,2-trifluoroethanol at 20℃; for 0.166667h; Microwave irradiation; Stage #2: Benzyl isocyanide; 1H-Indazole-3-carboxylic acid In N,N-dimethyl-formamide at 20 - 110℃; Microwave irradiation;	95%

...Expand

: 952182-03-5
oxetan-3-yl-methylamine

: 4498-67-3
1H-Indazole-3-carboxylic acid

: N-methyl-N-(oxetan-3-yl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h; Reagent/catalyst; Temperature; Solvent;	94%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 74-89-5
methylamine

: 32387-21-6
1-methyl-3-indolecarboxylic acid

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With tin(ll) chloride In acetonitrile at 55℃; for 6h; Stage #2: methylamine In acetonitrile at 9℃; for 41h; Temperature; Reflux;	93%

: 479079-15-7, 479080-20-1
tert-butyl [2-amino-2-(hydroxyimino)ethyl]carbamate

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 1151512-97-8
tert-butyl 2-(1H-indazole-3-carbonyloxyimino)-2-aminoethylcarbamate

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	92%
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate In N,N-dimethyl-formamide at 20℃;	92%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 72083-74-0
1H-indazole-3-carbonyl chloride

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 2h; Inert atmosphere;	91%
With thionyl chloride for 1h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 2h;
With thionyl chloride for 8h; Reflux;
With thionyl chloride at 80℃; for 4h;

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 77-78-1
dimethyl sulfate

: 1-methylindazole-3-carboxylic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium methylate In methanol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In methanol for 3h; Heating / reflux; Stage #3: With hydrogenchloride In water for 2h; pH=1;	87.7%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 1077-94-7
5-bromobenzopyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With bromine; acetic acid at 90 - 120℃; for 16h;	87.5%
Stage #1: 1H-Indazole-3-carboxylic acid With acetic acid at 120℃; Stage #2: With bromine; acetic acid at 90℃; for 16h;	87.5%
With bromine; acetic acid at 90 - 120℃; for 16h;	87.5%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 77-78-1
dimethyl sulfate

: 50890-83-0
1-methyl-1H-indazole-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In methanol for 4h; Heating / reflux;	85.6%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium n-propylate In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 5h; Heating / reflux;	83.8%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium ethylate In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;	79.2%
Stage #1: 1H-Indazole-3-carboxylic acid With barium(II) oxide In propan-1-ol for 2h; Heating / reflux; Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;	65.4%

: 50541-93-0
4-amino-1-benzylpiperidine

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 207296-87-5
N-(1-benzylpiperidin-4-yl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In DMF (N,N-dimethyl-formamide) at 60℃; for 2h; Stage #2: 4-amino-1-benzylpiperidine In DMF (N,N-dimethyl-formamide) at 60℃; for 2h;	85.1%
With 1,1'-carbonyldiimidazole 1.) DMF, 60 deg C, 2 h, 2.) DMF, 60 deg C, 2 h; Yield given. Multistep reaction;
In N-methyl-acetamide; dichloromethane; 1,1'-carbonyldiimidazole	76%.

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 351457-12-0
1H-indazole-3-carboxylic acid methoxy(methyl)amide

Conditions

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 1H-Indazole-3-carboxylic acid With pyridine In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Stage #2: With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	85%
With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0 - 20℃; for 13.5h;	84%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 1H-Indazole-3-carboxylic acid With pyridine In tetrahydrofuran at 0 - 20℃; for 2.5h; Stage #2: With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	84%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 43120-28-1
methyl 1H-indazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methanol With acetyl chloride at 0℃; for 0.166667h; Stage #2: 1H-Indazole-3-carboxylic acid at 0 - 20℃;	85%
With sodium bicarbonate; sulfuric acid In methanol	61%
In methanol

: 18703-07-6, 74741-94-9, 162117-95-5
oxotribromobis(triphenylphosphine)rhenium(V)

: 4498-67-3
1H-Indazole-3-carboxylic acid

: [ReO(bromide)2(indazole-3-carboxylate)(triphenylphosphine)]*(triphenylphosphine oxide)

Conditions

Conditions	Yield
With air In tetrahydrofuran byproducts: HBr, P(C6H5)3; addn. of Re complex to N compd. (1:1) in C4H8O, heating under reflux for4 h; concn., cooling to room temp., slow diffusion of diethyl ether, isolation of crystals, elem. anal.;	85%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 90004-04-9
1H-indazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 2h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 1h;	85%
Stage #1: 1H-Indazole-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 2h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere;	85%
Stage #1: 1H-Indazole-3-carboxylic acid With thionyl chloride for 3h; Inert atmosphere; Reflux; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 0.5h; Inert atmosphere;	76%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 74-88-4
methyl iodide

: 50890-83-0
1-methyl-1H-indazole-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux; Stage #2: methyl iodide In methanol at 20℃; for 26h; Heating / reflux;	83.8%
With hydrogenchloride; sodium chloride; sodium hydrogencarbonate In dimethyl sulfoxide; mineral oil

: 90-04-0
2-methoxy-phenylamine

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 23707-04-2
N-(2-methoxyphenyl)-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	70%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 36209-49-1
4-amino-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol

: 3-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl]-1H-indazole

Conditions

Conditions	Yield
With trichlorophosphate at 90 - 95℃;	82%

: 62-53-3
aniline

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 23706-99-2
1H-indazole-3-carboxylic acid phenylamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃;	81%
Stage #1: 1H-Indazole-3-carboxylic acid With thionyl chloride for 3h; Inert atmosphere; Reflux; Stage #2: aniline In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	70%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 48h;	64%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h;	59%

: 4498-67-3
1H-Indazole-3-carboxylic acid

: 76272-58-7
(±)-(1R,3r,5S)-9-benzyl-9-azabicyclo[3.3.1]nonan-3-yl acetate

: 1210745-16-6
N-[(3-endo)-9-(phenylmethyl)-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1H-Indazole-3-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: (±)-(1R,3r,5S)-9-benzyl-9-azabicyclo[3.3.1]nonan-3-yl acetate In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	81%

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

Product Name

Indazole-3-carboxylic acid

Synthetic route

Indazole-3-carboxylic acid Specification

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