- Chemical Name 2-Nitroanisole
- CAS No. 91-23-6
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- Molecular Formula: C7H7NO3
- Molecular Weight: 153.137
- Appearance/Colour: yellow to amber liquid
- Melting Point: 9-12 °C(lit.)
- Refractive Index: 1.5603
- Boiling Point: 277 °C at 760 mmHg
- Flash Point: 127 °C
- PSA： 55.05000
- Density: 1.222 g/cm3
- LogP: 2.12660
2-Nitroanisole(Cas 91-23-6) Usage
|
General Description |
2-Nitroanisole, also known as o-nitroanisole or 1-methoxy-2-nitrobenzene, is a chemical compound with the formula C7H7NO3. It is characterized as an aromatic, yellow liquid with a pleasant smell which is insoluble in water but soluble in ethanol and ether. It is used in various applications such as perfumery and flavoring agent. Furthermore, 2-Nitroanisole is utilized as an intermediate in the production of other chemical compounds. However, this substance can be harmful if ingested, inhaled or absorbed through the skin, making it important to handle with caution. |
InChI:InChI=1/C6H5NO2.C2H6O/c8-7(9)6-4-2-1-3-5-6;1-3-2/h1-5H;1-2H3
91-23-6 Relevant articles
-
Ismailski,Rosorenow
, (1923)
-
Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids
Richards, Kenza,Petit, Eddy,Legrand, Yves-Marie,Grison, Claude
supporting information, p. 809 - 814 (2020/11/30)
A new sustainable method is reported for...
Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium
Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.
, p. 25841 - 25847 (2021/08/09)
Regardless of the sustainable developmen...
High-efficiency green production process of o-aminoanisole
-
Paragraph 0031-0041, (2021/08/19)
The invention discloses a high-efficienc...
Selective Mild Oxidation of Anilines into Nitroarenes by Catalytic Activation of Mesoporous Frameworks Linked with Gold-Loaded Mn3O4 Nanoparticles
Armatas, Gerasimos S.,Daikopoulou, Vassiliki,Koutsouroubi, Eirini D.,Lykakis, Ioannis N.,Skliri, Euaggelia
, (2021/11/01)
This work reports the synthesis and cata...
91-23-6 Process route
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-
100-66-3
methoxybenzene
-
-
100-17-4
para-methoxynitrobenzene
-
-
91-23-6
2-Nitroanisole
| Conditions | Yield |
|---|---|
|
With
silica supported Al(NO3)3*9H2O;
In
acetone;
at 20 ℃;
for 0.75h;
regioselective reaction;
|
85%
13% |
|
With
sodium nitrite;
for 0.0333333h;
Reagent/catalyst;
Microwave irradiation;
|
12%
85% |
|
With
thionyl chloride; bismuth subnitrate;
In
dichloromethane;
at 20 ℃;
for 2h;
|
76%
12% |
|
With
2-chloro-1-methyl-pyridinium iodide; water; silica gel; sodium nitrite;
In
hexane;
at 20 ℃;
for 5h;
regioselective reaction;
|
75%
10% |
|
With
N-Bromosuccinimide; silver nitrate;
In
acetonitrile;
for 3.5h;
Reflux;
|
15%
74% |
|
With
3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide;
at 20 ℃;
for 2h;
Ionic liquid;
|
74%
20% |
|
With
nitro acetate; silica gel;
In
chloroform;
at -20 - 20 ℃;
|
70%
30% |
|
With
iodine; silver nitrate; chloro-diphenylphosphine;
In
dichloromethane;
at 20 ℃;
for 0.583333h;
|
19%
70% |
|
With
Iron(III) nitrate nonahydrate;
at 84.84 ℃;
for 0.25h;
regioselective reaction;
|
70%
30% |
|
With
ethylammonium nitrate; trifluoroacetic anhydride;
at 0 - 20 ℃;
for 0.583333h;
Inert atmosphere;
|
59%
|
|
With
aluminium trinitrate; acetic anhydride; scandium tris(trifluoromethanesulfonate);
In
acetonitrile;
at 20 ℃;
for 2h;
|
56%
25% |
|
With
ammonium nitrate; trifluoroacetic anhydride;
In
chloroform;
at 25 ℃;
for 2h;
|
55%
22% |
|
With
nitric acid; hydrazine;
at 25 ℃;
Rate constant;
other concetrations of acid, other temperatures;
|
54%
46% |
|
With
nitric acid;
at 0 ℃;
for 5h;
|
53%
26% |
|
With
aluminum oxide; dinitrogen tetraoxide;
In
tetrachloromethane;
for 1h;
Product distribution;
Mechanism;
Ambient temperature;
also in the presence of SiO2 or Al2O3; other solvents and reagents; other nitrating agents;
|
44%
16% |
|
With
air; nitrogen(II) oxide;
In
acetonitrile;
for 60h;
Ambient temperature;
|
38%
23% |
|
With
Iron(III) nitrate nonahydrate;
In
acetonitrile;
at 100 ℃;
for 24h;
Sealed tube;
Inert atmosphere;
|
26%
24% |
|
With
Iron(III) nitrate nonahydrate;
In
acetonitrile;
for 24h;
regioselective reaction;
Heating;
|
26%
24% |
|
With
iron(III) chloride hexahydrate; potassium nitrate;
at 60 ℃;
for 6h;
regioselective reaction;
Sealed tube;
Green chemistry;
|
25%
15% |
|
With
dinitrogen tetraoxide;
In
acetonitrile;
at 25 ℃;
Product distribution;
Kinetics;
electrochemical nitration (1.6 V), anode: Pt, cathode: Ni, electrolyte: Et4NBF4; same reaction in the system anisole-benzene or anisole-toluene (relative molar yield); polarization curves;
|
|
|
With
nitric acid; sodium nitrite;
In
tetrachloromethane;
at 25 ℃;
for 0.166667h;
Product distribution;
var. solvents;
|
|
|
With
ammonium cerium(IV) nitrate;
In
acetonitrile;
at 84 ℃;
Product distribution;
other reagent;
|
|
|
With
methane; MeNO3H(1-); oxygen; BRI;
at 37.5 ℃;
under 720 Torr;
Irradiation;
relative reactivity;
|
|
|
With
methyl nitrate; methane;
at 37.6 ℃;
Product distribution;
Irradiation;
gas-phase nitration by radiolytically formed MeO(1+)(H)NO2;
|
|
|
With
2,6-Me2PyNO2+BF4-;
In
acetonitrile;
at -40 ℃;
for 35h;
Product distribution;
Mechanism;
Irradiation;
other aromatic hydrocarbons, other substituted N-nitropyridinium derivatives; other temp. and time;
|
|
|
With
Nitrogen dioxide; ozone;
In
dichloromethane;
at 0 ℃;
Rate constant;
relative rates (competition with benzene), partial rate factors;
|
|
|
With
nitric acid;
|
|
|
With
bismuth(III) nitrate;
|
|
|
With
tetrabutylammonium nitrate; trifluoroacetic anhydride;
In
nitromethane;
at 25 ℃;
|
65.0 % Chromat.
35.0 % Chromat. |
|
With
methane; MeNO3H(1-); oxygen; BRI;
at 37.5 ℃;
under 720 Torr;
Yield given. Yields of byproduct given;
Irradiation;
|
|
|
With
nitric acid;
In
diethyl ether; water;
for 12h;
Yield given;
Ambient temperature;
|
|
|
With
cupric nitrate trihydrate supported on K 10 montmorillonite clay; nitric acid; acetic anhydride;
In
tetrachloromethane;
for 0.25h;
Yield given. Yields of byproduct given;
Ambient temperature;
|
|
|
With
tetrabutylammonium nitrate; trifluoroacetic anhydride;
In
various solvent(s);
at 25 ℃;
|
18.1 % Chromat.
81.9 % Chromat. |
|
With
nitric acid;
zeolite beta-I;
|
|
|
With
ammonium nitrate; diisopropylethylammonium trifluoroacetate; trifluoroacetic anhydride;
at 20 ℃;
Title compound not separated from byproducts;
|
|
|
With
isopentyl nitrate; trifluorormethanesulfonic acid; 1-ethyl-3-methylimidazolium triflate;
at 0 ℃;
Title compound not separated from byproducts;
|
|
|
With
perchloric acid; montmorillonite K10 supported ammonium nitrate;
at -5 ℃;
for 1h;
Title compound not separated from byproducts;
|
|
|
With
nitric acid; 1-(n-butyl)-3-methylimidazolium triflate;
at 50 ℃;
for 3h;
|
|
|
With
benzyltriphenylphosphonium nitrate; Methanesulfonic anhydride;
at 20 ℃;
for 0.0833333h;
|
|
|
With
nitric acid; acetic anhydride; 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide;
at 25 ℃;
for 1h;
Further Variations:;
Reagents;
Product distribution;
|
|
|
With
Zn(NO3)2*2N2O4;
at 20 ℃;
for 0.0833333h;
|
|
|
With
nitric acid; phosphorus pentoxide; silica gel;
at 20 ℃;
for 0.0333333h;
Title compound not separated from byproducts;
|
|
|
With
bismuth(III) nitrate; sulfuric acid; silica gel;
at 25 ℃;
for 0.0333333h;
Title compound not separated from byproducts;
|
|
|
With
[bmpy][N(Tf)2]; nitric acid; acetic anhydride;
at 25 ℃;
for 1h;
Further Variations:;
Reagents;
Product distribution;
|
|
|
With
nitric acid; acetic anhydride; 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide;
at 25 ℃;
for 1h;
Further Variations:;
Reagents;
Product distribution;
|
|
|
With
ammonium cerium(IV) nitrate; 1-ethyl-3-methylimidazolium triflate;
at 100 ℃;
for 6h;
|
|
|
With
nitric acid; acetic anhydride;
H5PV2Mo10O40(1,11);
for 3h;
Title compound not separated from byproducts.;
Heating;
|
70 % Chromat.
30 % Chromat. |
|
With
bismuth (III) nitrate pentahydrate;
for 1.5h;
Overall yield = 100 %Chromat.;
Ionic liquid;
Schlenk technique;
Inert atmosphere;
Heating;
|
|
|
With
bismuth(lll) trifluoromethanesulfonate; dinitrogen pentoxide;
In
dichloromethane;
at 0 ℃;
for 2h;
Overall yield = 99 %;
Green chemistry;
|
|
|
With
nitric acid;
In
1,2-dichloro-ethane;
at 20 ℃;
for 0.5h;
Reagent/catalyst;
|
|
|
With
nitric acid;
at 0 ℃;
for 0.0833333h;
Overall yield = 90 %;
Kinetics;
|
|
|
With
bismuth (III) nitrate pentahydrate;
for 1h;
Molecular sieve;
|
71.4 %Spectr.
28.6 %Spectr. |
|
With
dinitrogen pentoxide;
at 20 ℃;
for 0.0833333h;
under 4500.45 Torr;
Overall yield = 99 percent;
Autoclave;
Green chemistry;
|
-
-
598-58-3
methyl nitrate
-
-
100-66-3
methoxybenzene
-
-
100-17-4
para-methoxynitrobenzene
-
-
91-23-6
2-Nitroanisole
| Conditions | Yield |
|---|---|
|
Product distribution;
gas-phase radiolytic nitration;
|
91-23-6 Upstream products
-
74-87-3
methylene chloride
-
824-39-5
sodium o-nitrophenate
-
616-42-2
dimethylsulfite
-
610-67-3
1-ethoxy-2-nitrobenzene
91-23-6 Downstream products
-
88-75-5
2-hydroxynitrobenzene
-
108540-67-6
2,2,2-trichloro-1-(4-methoxy-3-nitro-phenyl)-ethanol
-
89264-24-4
1,1,1-trichloro-2,2-bis(4-methoxy-3-nitrophenyl)ethane
-
101273-21-6
1,1,1-trichloro-2-(2-methoxy-3-nitro-phenyl)-2-(4-methoxy-3-nitro-phenyl)-ethane
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