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3-Methyl-6-nitroindazole
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Name

3-Methyl-6-nitroindazole

 EINECS 613-731-0
CAS No. 6494-19-5 Density 1.438 g/cm3
PSA 74.50000 LogP 2.30270
Solubility N/A 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 N/A Appearance N/A
Safety 24/25-36/37 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 6494-19-5 (3-Methyl-6-nitroindazole) Hazard Symbols N/A
Synonyms

3-Methyl-6-nitro-1h-indazole;

Article Data 15

3-Methyl-6-nitroindazole Synthetic route

20191-74-6

2-ethyl-5-nitroaniline

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

6494-19-5

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

Conditions
ConditionsYield
With acetic acid
578-54-1

ortho-ethylaniline

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
6494-19-5

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

98-59-9

p-toluenesulfonyl chloride

62271-21-0

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

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃;100%
110-87-2

3,4-dihydro-2H-pyran

6494-19-5

3-methyl-6-nitro-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%
6494-19-5

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

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

24424-99-5

di-tert-butyl dicarbonate

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;
6494-19-5

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

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;
6494-19-5

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

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%
6494-19-5

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

74-88-4

methyl iodide

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-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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