Copyright 1988-2001 Beilstein Institut zur Foerderung der
Chemischen Wissenschaften. All rights reserved.
Reaction (BS0203AE:Reactions:Q02 hit 9, RX.ID 657713)
Reaction ID 657713
Reactant BRN 506892 methoxybenzene
Product BRN 1868032 1-methoxy-2-nitro- benzene 1865361 1-methoxy-4-nitro- benzene
No. of Reaction 29
Details
Field Availability List (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Code Field Name Occ.
RX Reaction 29 Details
Reaction Details 1 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent NH4NO3 TFAA [HNEtPri2][CF3COO]
Temperature 20 C
Note 1 Title compound not separated from byproducts
Ref. 1 6262670;LitLink; Journal; Laali, Kenneth K.; Gettwert, Volker J.; JOCEAH; J.Org.Chem.; EN; 66; 1; 2001; 35 - 40.
Reaction Details 2 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent isoamyl nitrate TfOH [emim][OTf]
Temperature 0 C
Note 1 Title compound not separated from byproducts
Ref. 1 6262670;LitLink; Journal; Laali, Kenneth K.; Gettwert, Volker J.; JOCEAH; J.Org.Chem.; EN; 66; 1; 2001; 35 - 40.
Reaction Details 3 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificati
on
Reagent HNO3
Catalyst zeolite beta-I
Reaction Nitration
Type
Ref. 1 6217685;LitLink; Journal; Choudary, B. M.; Sateesh, M.; Kantam, M. Lakshmi; Rao, K. Koteswara; Prasad, K. V. Ram; Raghavan, K. V.; Sarma, J. A. R. P.; CHCOFS; Chem.Commun.; EN; 1; 2000; 25 - 26.
Reaction Details 4 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Yield 70 percent (BRN=1868032) 30 percent (BRN=1865361)
Reagent acetyl nitrate silica
Solvent CHCl3
Temperature -20 - 20 C
Reaction Type Nitration
Ref. 1 6184050;LitLink; Journal; Rodrigues, J. Augusto R.; Filho, Antonio Pedro de Oliveira; Moran, Paulo J. S.; Custodio, Rogerio; TETRAB; Tetrahedron; EN; 55; 22; 1999; 6733 - 6738.
Reaction Details 5 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Yield 23 percent (BRN=1865361) 38 percent (BRN=1868032)
Reagent NO, air
Solvent acetonitrile
Time 60 hour(s)
Other Ambient temperature
Conditions
Ref. 1 6065420;LitLink; Journal; Mizuno, Kazuhiko; Tamai, Toshiyuki; Hashida, Isao; Otsuji, Yoshio; Inoue, Hiroo; JRPSDC; J.Chem.Res.Synop.; EN; 7; 1995; 284-285.
Reaction Details 6 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Yield 38 percent (BRN=1868032) 23 percent (BRN=1865361)
Reagent NO, air
Solvent acetonitrile
Time 60 hour(s)
Other Ambient temperature
Conditions
Ref. 1 6065420;LitLink; Journal; Mizuno, Kazuhiko; Tamai, Toshiyuki; Hashida, Isao; Otsuji, Yoshio; Inoue, Hiroo; JRPSDC; J.Chem.Res.Synop.; EN; 7; 1995; 284-285.
Reaction Details 7 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Reagent cupric nitrate trihydrate supported on K 10 montmorillonite clay, 100percent HNO3, Ac2O
Solvent CCl4
Time 15 min
Other Ambient temperature
Conditions
Note 1 Yield given. Yields of byproduct given
Ref. 1 5963484;LitLink; Journal; Gigante, Barbara; Prazeres, Angela O.; Marcelo-Curto, Maria J.; Cornelis, Andre; Laszlo, Pierre; JOCEAH; J.Org.Chem.; EN; 60; 11; 1995; 3445-3447.
Reaction Details 8 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Reagent cupric nitrate trihydrate supported on K 10 montmorillonite clay, 100percent HNO3, Ac2O
Solvent CCl4
Time 15 min
Other Ambient temperature
Conditions
Note 1 Yield given. Yields of byproduct given
Ref. 1 5963484;LitLink; Journal; Gigante, Barbara; Prazeres, Angela O.; Marcelo-Curto, Maria J.; Cornelis, Andre; Laszlo, Pierre; JOCEAH; J.Org.Chem.; EN; 60; 11; 1995; 3445-3447.
Reaction Details 9 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent 12N HNO3
Solvent diethyl ether H2O
Time 12 hour(s)
Other Ambient temperature
Conditions
Note 1 Yield given
Ref. 1 5800162;LitLink; Journal; Gaude, D.; Goaller, R. Le; Pierre, J. L.; SYNCAV; Synth.Commun.; EN; 16; 1; 1986; 63-68.
Reaction Details 10 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent 12N HNO3
Solvent diethyl ether H2O
Time 12 hour(s)
Other Ambient temperature
Conditions
Note 1 Yield given
Ref. 1 5800162;LitLink; Journal; Gaude, D.; Goaller, R. Le; Pierre, J. L.; SYNCAV; Synth.Commun.; EN; 16; 1; 1986; 63-68.
Reaction Details 11 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Reagent MeNO3H(1-)/methane, O2, SF6
Temperature 37.5 C
Pressure 720.0002 Torr
Other Irradiation
Conditions
Note 1 Yield given. Yields of byproduct given
Ref. 1 5687943;LitLink; Journal; Attina, Marina; Cacace, Fulvio; Petris, Giulia de; ANCEAD; Angew.Chem.; GE; 99; 11; 1987; 1174-1175.
Reaction Details 12 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificatio
n
Reagent MeNO3H(1-)/methane, O2, SF6
Temperature 37.5 C
Pressure 720.0002 Torr
Other Irradiation
Conditions
Note 1 Yield given. Yields of byproduct given
Ref. 1 5687943;LitLink; Journal; Attina, Marina; Cacace, Fulvio; Petris, Giulia de; ANCEAD; Angew.Chem.; GE; 99; 11; 1987; 1174-1175.
Reaction Details 13 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Yield 65.0 percent Chromat. (BRN=1868032) 35.0 percent Chromat (BRN=1865361)
Reagent Bu4NNO3, TFAA
Solvent nitromethane
Temperature 25 C
Ref. 1 5608860;LitLink; Journal; Masci, Bernardo; TETRAB; Tetrahedron; EN; 45; 9; 1989; 2719- 2730.
Reaction Details 14 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Yield 18.1 percent Chromat. (BRN=1865361) 81.9 percent Chromat (BRN=1868032)
Reagent Bu4NNO3, TFAA
Solvent various solvent(s)
Temperature 25 C
Ref. 1 5608860;LitLink; Journal; Masci, Bernardo; TETRAB; Tetrahedron; EN; 45; 9; 1989; 2719- 2730.
Reaction Details 15 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Yield 22 percent (BRN=1865361) 55 percent (BRN=1868032)
Reagent NH4NO3, Trifluoroacetic Anhydride
Solvent CHCl3
Time 2 hour(s)
Temperature 25 C
Ref. 1 5572557;LitLink; Journal; Crivello, J.V.; JOCEAH; J.Org.Chem.; EN; 46; 15; 1981; 3056- 3060.
Reaction Details 16 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Yield 55 percent (BRN=1868032) 22 percent (BRN=1865361)
Reagent NH4NO3, Trifluoroacetic Anhydride
Solvent CHCl3
Time 2 hour(s)
Temperature 25 C
Ref. 1 5572557;LitLink; Journal; Crivello, J.V.; JOCEAH; J.Org.Chem.; EN; 46; 15; 1981; 3056- 3060.
Reaction Details 17 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificati
on
Reagent concentrated nitric acid
Ref. 1 1512420;LitLink; Journal; Brunck; Zeitschrift fuer Chemie; 1867; 205; JCVWAE; Jahresber.Fortschr.Chem.Verw.Theile Anderer Wiss.; 1867; 619.
Ref. 2 1512510;LitLink; Journal; Cahours; ANCPAC; Ann.Chim.(Paris); <3> 27; 1849; 465; JLACBF; Justus Liebigs Ann. Chem.; 74; 1850; 315.
Reaction Details 18 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classificati
on
Reagent concentrated nitric acid
Ref. 1 1512420;LitLink; Journal; Brunck; Zeitschrift fuer Chemie; 1867; 205; JCVWAE; Jahresber.Fortschr.Chem.Verw.Theile Anderer Wiss.; 1867; 619.
Ref. 2 1512510;LitLink; Journal; Cahours; ANCPAC; Ann.Chim.(Paris); <3> 27; 1849; 465; JLACBF; Justus Liebigs Ann. Chem.; 74; 1850; 315.
Reaction Details 19 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent bismuth nitrate
Ref. 1 1536816;LitLink; Journal; Spiegel; Haymann; CHBEAM; Chem.Ber.; 59; 1926; 203.
Reaction Details 20 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Preparation
Classification
Reagent bismuth nitrate
Ref. 1 1536816;LitLink; Journal; Spiegel; Haymann; CHBEAM; Chem.Ber.; 59; 1926; 203.
Reaction Details 21 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificatio
n
Reagent NO2, O3
Solvent CH2Cl2
Temperature 0 C
Other relative rates (competition with benzene),
Conditions partial rate factors
Subject Rate constant
Studied
Ref. 1 5817405;LitLink; Journal; Suzuki, Hitomi; Murashima, Takashi; Kozai, Iku; Mori, Tadashi; JCPRB4; J.Chem.Soc.Perkin Trans.1; EN; 14; 1993; 1591-1598.
Reaction Details 22 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificatio
n
Yield 44 percent (BRN=1865361) 16 percent (BRN=1868032)
Reagent Al2O3, N2O4
Solvent CCl4
Time 1 hour(s)
Other Ambient temperature
Conditions also in the presence of SiO2 or Al2O3; other solvents and reagents; other nitrating agents
Subject Product distribution
Studied Mechanism
Ref. 1 5751781;LitLink; Journal; Nagy, S. M.; Zubkov, E. A.; Shubin, V. G.; Pelmenschikov, A. G.; Paukshtis, E. A.; Razdobarova, Natalia L.; ACHUDC; Acta Chim.Hung.; EN; 129; 5; 1992; 579-586.
Reaction Details 23 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificatio
n
Reagent 2,6-Me2PyNO2+BF4-
Solvent acetonitrile
Time 35 hour(s)
Temperature -40 C
Other Irradiation
Conditions other aromatic hydrocarbons, other substituted N-nitropyridinium derivatives; other temp. and time
Subject Product distribution
Studied Mechanism
Ref. 1 5751309;LitLink; Journal; Kim, E. K.; Bockman, T. M.; Kochi, J. K.; JACSAT; J.Amer.Chem.Soc.; EN; 115; 8; 1993; 3091- 3104.
Reaction Details 24 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classification
Reagent CH4, MeNO3
Temperature 37.6 C
Other Irradiation
Conditions gas-phase nitration by radiolytically formed MeO(1+)(H)NO2
Subject Product distribution
Studied
Ref. 1 5727699;LitLink; Journal; Attina, Marina; Cacace, Fulvio; JACSAT; J.Amer.Chem.Soc.; EN; 108; 2; 1986; 318-319.
Reaction Details 25 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificatio
n
Reagent MeNO3H(1-), methane, O2, SF6
Temperature 37.5 C
Pressure 720.0002 Torr
Other Irradiation
Conditions relative reactivity
Ref. 1 5687943;LitLink; Journal; Attina, Marina; Cacace, Fulvio; Petris, Giulia de; ANCEAD; Angew.Chem.; GE; 99; 11; 1987; 1174-1175.
Reaction Details 26 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classification
Reagent cerium (IV) ammonium nitrate
Solvent acetonitrile
Temperature 84 C
Other other reagent
Conditions
Subject Product distribution
Studied
Ref. 1 5620658;LitLink; Journal; Dinctuerk, Suphi; Ridd, John H.; JCPKBH; J.Chem.Soc.Perkin Trans.2; EN; 1982; 965-970.
Reaction Details 27 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classification
Yield 54 percent (BRN=1868032) 46 percent (BRN=1865361)
Reagent aq. nitric acid, hydrazine
Temperature 25 C
Other other concetrations of acid, other
Conditions temperatures
Subject Rate constant
Studied
Ref. 1 5611257;LitLink; Journal; Draper, Mark R.; Ridd, John H. A.; JCPKBH; J.Chem.Soc.Perkin Trans.2; EN; 1981; 94-99.
Reaction Details 28 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificatio
n
Reagent 65percent nitric acid, sodium nitrite
Solvent CCl4
Time 10 min
Temperature 25 C
Other var. solvents
Conditions
Subject Product distribution
Studied
Ref. 1 5528428;LitLink; Journal; Germain, Alain; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 23; 1990; 1697-1698.
Reaction Details 29 of 29 (BS0203AE:Reactions:Q02 hit 9,
RX.ID 657713)
Reaction Chemical behaviour
Classificati
on
Reagent N2O4
Solvent acetonitrile
Temperature 25 C
Other electrochemical nitration (1.6 V), anode: Pt,
Conditions cathode: Ni, electrolyte: Et4NBF4; same reaction in the system anisole-benzene or anisole-toluene (relative molar yield); polarization curves
Subject Product distribution
Studied Kinetics
Ref. 1 5521176;LitLink; Journal; Evtyugin, G. A.; Semanov, D. A.; Rydvanskii, Yu. V.; Iskanderov, R. R.; Latypova, V. Z.; Kargin, Yu. M.; JGCHA4; J.Gen.Chem.USSR (Engl.Transl.); EN; 59; 10; 1989; 2089-2093; ZOKHA4; Zh.Obshch.Khim.; RU; 59; 10; 1989; 2331-2336.