Production Method 1

880-93-3

Reaction Conditions

1.1 Reagents: Nitric acid Solvents: Acetic acid ,  Water ;  cooled; 30 min, cooled; 5 h, rt
1.2 Solvents: Water ;  5 min, cooled

Reference

Design, synthesis and biological activity of tetrazole-bearing uric acid transporter 1 inhibitors

Cai, Wenqing; Liu, Wei; Xie, Yafei; Wu, Jingwei; Liu, Yuqiang; et al, Chemical Research in Chinese Universities, 2017, 33(1), 49-60

Production Method 2

880-93-3

Reaction Conditions

1.1 Reagents: Nitric acid ;  0 °C

Reference

A Facile Synthesis of Benzo[h]quinolines via Silica-TsOH-P2O5 Promoted Condensation of 1-Naphthylamines with 1,3-Diketones under Solvent Free Conditions

Zhu, Chuanlei; Guo, Ruiqiang; Sheng, Zhe; Li, Yanzhe; Chu, Changhu, Chinese Journal of Chemistry, 2017, 35(10), 1595-1600

Production Method 3

880-93-3

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid ;  1 h, rt

Reference

Optimization of Alkylidene Hydrazide Based Human Glucagon Receptor Antagonists. Discovery of the Highly Potent and Orally Available 3-Cyano-4-hydroxybenzoic Acid [1-(2,3,5,6-Tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide

Madsen, Peter; Ling, Anthony; Plewe, Michael; Sams, Christian K.; Knudsen, Lotte B.; et al, Journal of Medicinal Chemistry, 2002, 45(26), 5755-5775

Production Method 4

880-93-3

Reaction Conditions

1.1 Reagents: Nitric oxide

Reference

Formation of methylnitronaphthalenes from the gas-phase reactions of 1- and 2-methylnaphthalene with hydroxyl radicals and nitrogen oxide (N2O5) and their occurrence in ambient air

Zielinska, Barbara; Arey, Janet; Atkinson, Roger; McElroy, Patricia A., Environmental Science and Technology, 1989, 23(6), 723-9

Production Method 5

4900-63-4

917-64-6

880-93-3

Reaction Conditions

Reference

Stereochemical study on nitro tautomerization of nitronate adducts from conjugate addition of RMgX to a 4-methoxy-1-nitronaphthalene system

Bartoli, Giuseppe; Bosco, Marcella; Baccolini, Graziano, Journal of Organic Chemistry, 1980, 45(13), 2649-53

Production Method 6

880-93-3

Reaction Conditions

1.1 Reagents: Sodium nitrate ,  Potassium nitrate ,  Silver nitrate ;  160 °C
1.2 Catalysts: Potassium ferrocyanide ;  30 s, 160 °C
1.3 1 h, 160 °C

Reference

Aromatic Nitration in Liquid Ag0.51K0.42Na0.07NO3

Mascal, Mark; Yin, Lunxiang; Edwards, Ross; Jarosh, Michael, Journal of Organic Chemistry, 2008, 73(16), 6148-6151

Production Method 7

103986-53-4

880-93-3

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite ,  Oxygen Solvents: Acetonitrile ;  12 h, 50 °C

Reference

Green and controllable metal-free nitrification and nitration of arylboronic acids

Wang, Shuai; Shu, Chun Chun; Wang, Tao; Yu, Jian; Yan, Guo Bing, Chinese Chemical Letters, 2012, 23(6), 643-646

Production Method 8

103986-53-4

880-93-3

Reaction Conditions

1.1 Reagents: Tetrabutylammonium nitrate ,  Oxygen Catalysts: Copper oxide (CuO) Solvents: Acetonitrile ;  8 - 12 h, rt

Reference

Copper-catalyzed nitration of arylboronic acids with nitrite salts under mild conditions: an efficient synthesis of nitroaromatics

Yan, Guobing; Zhang, Ling; Yu, Jian, Letters in Organic Chemistry, 2012, 9(2), 133-137

Production Method 9

880-93-3

63017-87-8

Reaction Conditions

1.1 Reagents: Nitric acid Catalysts: Copper(II) triflate Solvents: 1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide

Reference

Green synthesis: Aromatic nitrations in room-temperature ionic liquids

Handy, Scott T.; Egrie, Cristina R., ACS Symposium Series, 2002, 818, 134-146

Production Method 10

880-93-3

Reaction Conditions

1.1 Reagents: Nitrogen dioxide

Reference

Thermal and Photochemical Nitration of Aromatic Hydrocarbons with Nitrogen Dioxide

Bosch, E.; Kochi, J. K., Journal of Organic Chemistry, 1994, 59(12), 3314-25

Production Method 11

880-93-3

Reaction Conditions

1.1 Reagents: Acetic anhydride Solvents: Acetonitrile

Reference

Charge-transfer nitration of naphthalene and the methylnaphthalenes. Part 1. Direct comparison with electrophilic aromatic nitrations

Sankararaman, S.; Kochi, J. K., Journal of the Chemical Society, 1991, (1), 1-12

Production Method 12

880-93-3

Reaction Conditions

1.1 Reagents: Nitric acid

Reference

Preparation of a series of substituted fluoromethylnaphthalenes

Dixon, Elisabeth A.; Fischer, Alfred; Robinson, Frank P., Canadian Journal of Chemistry, 1981, 59(17), 2629-41

1-Methyl-4-nitronaphthalene Raw materials

• 4-Methyl-1-naphthaleneboronic acid
• 1-Methoxy-4-nitronaphthalene
• Methylmagnesium Iodide (3.0 M in Diethyl ether)

1-Methyl-4-nitronaphthalene Preparation Products

• 1-methyl-2-nitronaphthalene (63017-87-8)
• 1-Methyl-4-nitronaphthalene (880-93-3)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Nitronaphthalenes

• 54755-20-3(Naphthalene,6-methyl-1-nitro-)
• 102630-62-6(Anthracene,2-methyl-9-nitro-)
• 89597-18-2(Anthracene, 1-methyl-3-nitro-)
• 89198-47-0(Pyrene, 1-methyl-8-nitro-)
• 54558-94-0(Naphthalene, 1,5-dimethyl-4,8-dinitro-)
• 86689-95-4(Anthracene,1-methyl-10-nitro-)
• 116530-07-5(Naphthalene,1-methyl-7-nitro-)
• 124390-37-0(Chrysene,5-methyl-12-nitro-)
• 105752-67-8(Naphthalene,1-methyl-6-nitro-)
• 88535-51-7(Pyrene, 4-methyl-3-nitro-)