Product Name

  • Name

    3-Methyl-6-nitroindazole

  • EINECS 613-731-0
  • CAS No. 6494-19-5
  • Article Data15
  • CAS DataBase
  • Density 1.438 g/cm3
  • Solubility
  • Melting Point 187-188 °C
  • Formula C8H7N3O2
  • Boiling Point 225.226 °C at 760 mmHg
  • Molecular Weight 177.162
  • Flash Point 90.014 °C
  • Transport Information
  • Appearance
  • Safety 24/25-36/37
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 6494-19-5 (3-Methyl-6-nitroindazole)
  • Hazard Symbols
  • Synonyms 3-Methyl-6-nitro-1h-indazole;
  • PSA 74.50000
  • LogP 2.30270

Synthetic route

2-ethyl-5-nitroaniline
20191-74-6

2-ethyl-5-nitroaniline

3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With acetic acid; isopentyl nitrite at 20℃; for 0.75h;98%
With tert.-butylnitrite In acetic acid at 20℃; for 0.75h; Inert atmosphere;98%
With tert.-butylnitrite; acetic acid for 0.5h;98%
diazotized 2-ethyl-5-nitro-aniline

diazotized 2-ethyl-5-nitro-aniline

3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With acetic acid
ortho-ethylaniline
578-54-1

ortho-ethylaniline

3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; potassium nitrate / 1.5 h / 0 °C
2: acetic acid; isopentyl nitrite / 1.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 0.5 h / 0 - 5 °C
2: tert.-butylnitrite; acetic acid / 0.5 h
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

3-methyl-6-nitro-1-(toluene-4-sulfonyl)-1H-indazole
62271-21-0

3-methyl-6-nitro-1-(toluene-4-sulfonyl)-1H-indazole

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-methyl-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

3-methyl-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 12h;98%
With methanesulfonic acid In tetrahydrofuran at 80℃; for 8h; Inert atmosphere;74%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2,3-dimethyl-6-amino-2H-indazole
444731-72-0

2,3-dimethyl-6-amino-2H-indazole

Conditions
ConditionsYield
With ammonium formate; palladium 10% on activated carbon In methanol; water at 25 - 30℃; for 6h;96.7%
Multi-step reaction with 2 steps
1: sulfuric acid / N,N-dimethyl-formamide; toluene / 3 h / Reflux
2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol
View Scheme
Multi-step reaction with 2 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 0.25 h / 20 °C
1.2: 6 h / Reflux
2.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-methyl-6-nitro-1H-indazole-1-carboxylate
219507-74-1

tert-butyl 3-methyl-6-nitro-1H-indazole-1-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 192h;95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;70.28%
With triethylamine; dmap In dichloromethane at 20℃; for 3h;
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-methyl-1H-indazol-6-amine
79173-62-9

3-methyl-1H-indazol-6-amine

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0 - 100℃; for 0.583333h;92%
With nickel Hydrogenation;
With hydrogenchloride; water; iron Hydrogenation;
With ammonium formate; iron In ethanol; water at 90℃; for 2h;
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 10h;
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-methyl-1H-indazol-6-amine hydrochloride

3-methyl-1H-indazol-6-amine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In diethylene glycol dimethyl ether; water at 0 - 100℃; for 0.583333h; Cooling with ice; Inert atmosphere;92%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

methyl iodide
74-88-4

methyl iodide

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
Stage #1: 3-methyl-6-nitro-1H-indazole With sodium In isopropyl alcohol for 3h; Reflux;
Stage #2: methyl iodide In isopropyl alcohol for 5h; Reflux;		87.6%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2-fluoro-6-methoxybenzonitrile
94088-46-7

2-fluoro-6-methoxybenzonitrile

1-(2-cyano-3-methoxyphenyl)-3-methyl-6-nitroindazole

1-(2-cyano-3-methoxyphenyl)-3-methyl-6-nitroindazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Product distribution / selectivity;86.7%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,3-trimethyl-6-nitro-1H-indazol-2-ium perchlorate

1,2,3-trimethyl-6-nitro-1H-indazol-2-ium perchlorate

Conditions
ConditionsYield
Stage #1: 3-methyl-6-nitro-1H-indazole; dimethyl sulfate In toluene for 48h; Reflux;
Stage #2: With sodium perchlorate In water		86%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2-bromo-6-methoxybenzoic acid
31786-45-5

2-bromo-6-methoxybenzoic acid

1-(2-carboxy-3-methoxy)phenyl-3-methyl-6-nitro-1H-indazole
126955-75-7

1-(2-carboxy-3-methoxy)phenyl-3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;84%
With hydrogenchloride; potassium carbonate In water; nitrobenzene7.45 g (75.9%)
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
In ethyl acetate at 25 - 30℃; for 20h;82.4%
In acetone at 20℃; for 3h; Product distribution / selectivity;73%
In acetone at 20℃; for 3h;73%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
Stage #1: 3-methyl-6-nitro-1H-indazole With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: carbonic acid dimethyl ester In N,N-dimethyl-formamide for 6h; Reflux;		81.1%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide; isopropyl alcohol at 70℃; for 20h; Concentration; Reagent/catalyst; Temperature; Solvent;70.6%
With sodium hydride for 5h; Reflux;
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

dimethyl sulfate
77-78-1

dimethyl sulfate

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
With sulfuric acid In dimethyl sulfoxide at 50℃; for 72h; Product distribution / selectivity;70%
With sulfuric acid In dimethyl sulfoxide at 50℃; for 72h;70%
With sulfuric acid In dimethyl sulfoxide at 50℃; for 72h; Product distribution / selectivity;70%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

trimethyl orthoformate
149-73-5

trimethyl orthoformate

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In dichloromethane at -30 - 0℃; for 0.25h;
Stage #2: 3-methyl-6-nitro-1H-indazole In dichloromethane at 20℃; for 17h;		65%
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In dichloromethane at -30 - 0℃; for 0.25h;
Stage #2: 3-methyl-6-nitro-1H-indazole In dichloromethane at -70 - 20℃; for 17.25h;
Stage #3: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;		65%
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In dichloromethane at -30 - 0℃; for 0.283333h;
Stage #2: 3-methyl-6-nitro-1H-indazole In dichloromethane at -70 - 20℃; for 17.25h; Product distribution / selectivity;		65%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

Conditions
ConditionsYield
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In dichloromethane at -70 - 0℃; for 0.25h;
Stage #2: 3-methyl-6-nitro-1H-indazole In dichloromethane at -70 - 20℃; for 17.25h; Product distribution / selectivity;		65%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

A

2,3‑dimethyl‑6‑nitro‑2H‑indazole
444731-73-1

2,3‑dimethyl‑6‑nitro‑2H‑indazole

B

1,3-dimethyl-6-nitro-1H-indazole

1,3-dimethyl-6-nitro-1H-indazole

Conditions
ConditionsYield
Stage #1: 3-methyl-6-nitro-1H-indazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.75h;
Stage #2: carbonic acid dimethyl ester In N,N-dimethyl-formamide at 120℃; for 5h;		A 61%
B 33%
...Expand
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

1-(2-cyano-3-fluorophenyl)-3-methyl-6-nitroindazole
786658-39-7

1-(2-cyano-3-fluorophenyl)-3-methyl-6-nitroindazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h;32.5%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

ethanol
64-17-5

ethanol

1-(1-ethoxyethyl)-3-methyl-6-nitro-1H-indazole

1-(1-ethoxyethyl)-3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide In decane at 120℃; for 12h; Schlenk technique; Sealed tube;20%
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-methyl-6-nitro-1(2)H-indazol-7-ylamine
99584-38-0

3-methyl-6-nitro-1(2)H-indazol-7-ylamine

Conditions
ConditionsYield
With hydrogenchloride; propan-1-ol; sodium hydroxide; hydroxylamine
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

5-methyl-3-phenylisoxazole-4-carbonyl chloride
16883-16-2

5-methyl-3-phenylisoxazole-4-carbonyl chloride

3-methyl-1-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole
62235-34-1

3-methyl-1-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole

Conditions
ConditionsYield
With triethylamine In benzene
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-methyl-5-phenylisoxazole-4-carbonyl chloride
91182-77-3

3-methyl-5-phenylisoxazole-4-carbonyl chloride

3-methyl-1-(3-methyl-5-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole
62235-33-0

3-methyl-1-(3-methyl-5-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole

Conditions
ConditionsYield
With triethylamine In benzene
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride
25629-50-9

3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride

1-[3-(2-chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole
62235-35-2

1-[3-(2-chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With triethylamine In benzene
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride
4462-55-9

3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonyl chloride

1-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole
62235-36-3

1-[3-(2,6-dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-3-methyl-6-nitro-1H-indazole

Conditions
ConditionsYield
With triethylamine In benzene
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

5-bromo-7-hydroxy-2-methyl-6H-pyrazolo<4,5,1-de>acridin-6-one
142854-00-0

5-bromo-7-hydroxy-2-methyl-6H-pyrazolo<4,5,1-de>acridin-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
3: 47percent aq. HBr, NaNO2 / methanol
4: 47percent HBr, CuBr / methanol
5: NaOMe / methanol; H2O
6: CF3SO3H / 4 h / 100 °C
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

5-bromo-7-methoxy-2-methyl-6H-pyrazolo<4,5,1-de>acridin-6-one
142853-99-4

5-bromo-7-methoxy-2-methyl-6H-pyrazolo<4,5,1-de>acridin-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
3: 47percent aq. HBr, NaNO2 / methanol
4: 47percent HBr, CuBr / methanol
5: NaOMe / methanol; H2O
6: CF3SO3H / 4 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
3: 47percent aq. HBr, NaNO2 / methanol
4: 47percent HBr, CuBr / methanol
5: NaOMe / methanol; H2O
6: 1.) CF3SO3H; 2.) K2CO3 / 1.) 100 deg C, 4 h; 2.) acetone, 10 h, reflux
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

2-(6-Bromo-3-methyl-indazol-1-yl)-6-methoxy-benzoic acid
791559-34-7

2-(6-Bromo-3-methyl-indazol-1-yl)-6-methoxy-benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
3: 47percent aq. HBr, NaNO2 / methanol
4: 47percent HBr, CuBr / methanol
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

6-amino-1-(2-carboxy-3-methoxyphenyl)-3-methylindazole
142854-09-9

6-amino-1-(2-carboxy-3-methoxyphenyl)-3-methylindazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
View Scheme
3-methyl-6-nitro-1H-indazole
6494-19-5

3-methyl-6-nitro-1H-indazole

6-bromo-1-(2-carboxy-3-methoxy)phenyl-3-methyl-1H-indazole sodium salt

6-bromo-1-(2-carboxy-3-methoxy)phenyl-3-methyl-1H-indazole sodium salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84 percent / K2CO3, CuI / dimethylformamide / 6 h / 100 °C
2: 88 percent / NH2NH2*H2O / 10percent Pd-C / H2O; ethanol / 2 h / Heating
3: 47percent aq. HBr, NaNO2 / methanol
4: 47percent HBr, CuBr / methanol
5: NaOMe / methanol; H2O
View Scheme

3-Methyl-6-nitroindazole Chemical Properties


IUPAC Name: 1-Methyl-5-nitrobenzimidazole
Molecular Formula: C8H7N3O2
Molecular Weight: 177.16 g/mol
Canonical SMILES: [O-][N+](=O)c1ccc2c(c1)nnc2C
InChI: InChI=1/C8H7N3O2/c1-5-7-3-2-6(11(12)13)4-8(7)10-9-5/h2-4H,1H3,(H,9,10)
Mol File: 6494-19-5.mol
Product Categories: Heterocyclic Compound; Indole
Nominal Mass: 177
Average Mass: 177.1601
Monoisotopic Mass: 177.053826
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 74.5
Index of Refraction: 1.707
Molar Refractivity: 47.99 cm3
Molar Volume: 123.212 cm3
Polarizability: 19.025×10-24 cm3
Surface Tension: 71.261 dyne/cm
Density: 1.438 g/cm3
Flash Point: 90.014 °C
Enthalpy of Vaporization: 46.174 kJ/mol
Boiling Point: 225.226 °C at 760 mmHg
Melting Point: 187-188 °C
Vapour Pressure of 3-Methyl-6-nitroindazole (CAS NO.6494-19-5): 0.087 mmHg at 25 °C

3-Methyl-6-nitroindazole Specification

 3-Methyl-6-nitroindazole (CAS NO.6494-19-5), its Synonyms are 3-Methyl-6-nitro-1H-indazole ; 3-Methyl-6-nitro-1H-indazole ,99+% ; 3-Methyl-6-nitro-1H-indazole ,97% .

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