Production Method 1

14094-12-3

881-03-8

Reaction Conditions

1.1 Reagents: Potassium bis(trimethylsilyl)amide Solvents: Dimethylformamide ,  Tetrahydrofuran ;  30 min, -40 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Alkylation of Nitroarenes via Vicarious Nucleophilic Substitution - Experimental and DFT Mechanistic Studies

Antoniak, Damian; Paluba, Bartosz; Basak, Tymoteusz ; Blaziak, Kacper; Barbasiewicz, Michal, Chemistry - A European Journal, 2022, 28(46),

Production Method 2

881-03-8

Reaction Conditions

1.1 Solvents: Acetic acid ;  rt → 10 °C
1.2 Reagents: Nitric acid Solvents: Water ;  10 °C; 2 h, 10 °C

Reference

New types of very efficient photolabile protecting groups based upon the [2-(2-nitrophenyl)propoxy]carbonyl (NPPOC) moiety

Buehler, Sigrid; Lagoja, Irene; Giegrich, Heiner; Stengele, Klaus-Peter; Pfleiderer, Wolfgang, Helvetica Chimica Acta, 2004, 87(3), 620-659

Production Method 3

98750-90-4

881-03-8

2387583-38-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ;  30 min, -40 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems

Antoniak, Damian; Barbasiewicz, Michal, Organic Letters, 2019, 21(23), 9320-9325

Production Method 4

881-03-8

Reaction Conditions

1.1 Reagents: Fuming nitric acid Solvents: Acetic acid ,  Water ;  0 °C; 2 h, cooled

Reference

Mechanistic Insights into Allosteric Structure-Function Relationships at the M1 Muscarinic Acetylcholine Receptor

Abdul-Ridha, Alaa; Lane, J. Robert; Mistry, Shailesh N.; Lopez, Laura; Sexton, Patrick M.; et al, Journal of Biological Chemistry, 2014, 289(48), 33701-33711

Production Method 5

881-03-8

Reaction Conditions

1.1 Reagents: Acetic acid ,  Nitric acid ;  10 °C → rt

Reference

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide-alkyne click reaction

Malkova, Ksenia; Bubyrev, Andrey; Krivovicheva, Vasilisa; Dar'in, Dmitry; Bunev, Alexander ; et al, Beilstein Journal of Organic Chemistry, 2022, 18, 1636-1641

Production Method 6

881-03-8

Reaction Conditions

1.1 Reagents: Nitric acid Catalysts: Acetic acid

Reference

Synthesis of 1,4-sulfur-containing derivatives of 2-methylnaphthalene

Andreeva, M. A.; Budyak, E. V.; Perevalov, V. P.; Rodionov, V. Ya.; Stepanov, B. I.; et al, Izvestiya Vysshikh Uchebnykh Zavedenii, 1978, 21(1), 140-1

Production Method 7

881-03-8

Reaction Conditions

Reference

4-Amino-2-methyl-1-naphthalenesulfonic acid

Fierz-David, Hans E.; Mannhart, Emil, Helvetica Chimica Acta, 1937, 20, 1024-40

Production Method 8

881-03-8

Reaction Conditions

1.1 Reagents: Nitric acid Catalysts: Indium triflate Solvents: Water ;  4 h, rt; 20 h, 60 °C

Reference

Indium triflate as a recyclable catalyst for the nitration of aromatic compounds without a halogenated solvent

Yin, Wan-Po; Shi, Min, Journal of Chemical Research, 2006, (9), 549-551

Production Method 9

550-60-7

823-96-1

881-03-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Sulfonyl fluoride Solvents: 1,4-Dioxane ;  1 h, rt
1.2 Reagents: Tripotassium phosphate Catalysts: Palladium diacetate ,  [2′,6′-Bis(1-methylethoxy)[1,1′-biphenyl]-2-yl]dicyclohexylphosphine Solvents: 1,4-Dioxane ;  2 h, 120 °C
1.3 Reagents: Water

Reference

A late-stage functionalization tool: sulfonyl fluoride mediated deoxymethylation of phenols

Zhang, Guofu; Guan, Chenfei; Han, Linjun; Zhao, Yiyong; Ding, Chengrong, Organic & Biomolecular Chemistry, 2022, 20(38), 7640-7644

Production Method 10

881-03-8

Reaction Conditions

1.1 Reagents: Bismuth subnitrate Catalysts: Thionyl chloride Solvents: Dichloromethane ;  2 h, rt

Reference

Selective nitration of aromatic compounds with bismuth subnitrate and thionyl chloride

Muathen, Hussni A., Molecules, 2003, 8(7), 593-598

Production Method 11

881-03-8

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Sodium chloride ,  Nitric acid Catalysts: (Perfluoro-o-phenylene)mercury cyclic trimer Solvents: Benzene ,  Nitrobenzene ,  Water ;  6 h, 21 °C

Reference

Cyclic trimeric perfluoro-o-phenylenemercury: a highly efficient phase transfer catalyst for nitration of aromatic substrates with dilute nitric acid

Zaraisky, A. P.; Kachurin, O. I.; Velichko, L. I.; Tikhonova, I. A.; Furin, G. G.; et al, Journal of Molecular Catalysis A: Chemical, 2005, 231(1-2), 103-111

Production Method 12

881-03-8

Reaction Conditions

1.1 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 13

105-39-5

881-03-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  rt → -20 °C
1.2 Solvents: Tetrahydrofuran ;  7 min, -20 - -10 °C; 1 h, -10 - 0 °C
1.3 Solvents: Water ;  overnight
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 4
1.5 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  6 h, 50 °C

Reference

Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution

Achmatowicz, Michal; Thiel, Oliver R.; Gorins, Gilles; Goldstein, Corinne; Affouard, Caroline; et al, Journal of Organic Chemistry, 2008, 73(17), 6793-6799

Production Method 14

881-03-8

Reaction Conditions

1.1 Reagents: Nitric acid Solvents: Acetic acid

Reference

Novel functionalized indigo derivatives for organic electronics

Klimovich, Irina V. ; Zhilenkov, Alexander V.; Kuznetsova, Lidiya I.; Frolova, Lubov A.; Yamilova, Olga R.; et al, Dyes and Pigments, 2021, 186,

Production Method 15

1774-47-6

881-03-8

Reaction Conditions

1.1 Reagents: Magnesium chloride Solvents: Dimethylformamide
1.2 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Synthesis of 2,1-benzisoxazole derivatives from nitroarenes and CH acids in aprotic media

Wrobel, Z., Polish Journal of Chemistry, 1998, 72(11), 2384-2388

Production Method 16

4919-43-1

881-03-8

Reaction Conditions

1.1 Solvents: Acetic anhydride

Reference

Synthesis of new heterocycles: condensation of 2-methyl-4H-naphth[1,2-d][1,3]oxazin-4-one with Schiff bases and formation of 3-aryl-2-styrylbenzo[h]quinazolin-4(3H)-ones

Reddy, Mandala Satyanarayana; Ratnam, Chengalvala Venkata, Bulletin of the Chemical Society of Japan, 1985, 58(8), 2449-50

2-Methyl-1-nitronaphthalene Raw materials

• Trimethylsulfoxonium iodide
• ethyl 2-chloroacetate
• 1-Nitro-2-naphthol
• 1-Amino-2-naphthoic acid
• Benzene, (methylselenonyl)-
• Trimethylboroxin
• Propane,2-methyl-2-(methylsulfonyl)-

2-Methyl-1-nitronaphthalene Preparation Products

• 2-Methyl-1-nitronaphthalene (881-03-8)
• 1a,7b-Dihydro-7b-nitro-1H-cyclopropa[a]naphthalene (2387583-38-0)

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• 91754-89-1(Naphthalene, 2-methylnitro-)
• 1321-12-6(Benzene, methylnitro-)
• 54559-00-1(Naphthalene, 1,8-dimethyl-2,4,5-trinitro-)
• 37954-59-9(Methylene,(3,5-dimethyl-4-nitrophenyl)- (9CI))
• 89597-17-1(Anthracene, 2-methyl-3-nitro-)
• 105802-11-7(Chrysene,5-methyl-6-nitro-)
• 82308-93-8(Methylnitronaphthalene)
• 1204-72-4(Naphthalene,2-methyl-3-nitro-)
• 16275-25-5(Naphthalene,2,6-dimethyl-1,5-dinitro-)
• 89597-16-0(Anthracene, 2-methyl-1-nitro-)