Production Method 1

615-37-2

85448-89-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Palladium diacetate ,  2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane Solvents: Toluene ;  9 - 12 h, 80 °C

Reference

P(i-BuNCH2CH2)3N: an effective ligand in the palladium-catalyzed amination of aryl bromides and iodides

Urgaonkar, Sameer; et al, Journal of Organic Chemistry, 2003, 68(2), 452-459

Production Method 2

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: 1905460-14-1 Solvents: 1,4-Dioxane ;  4 h, 100 °C

Reference

Novel Pd-N-heterocyclic carbene complexes: design, synthesis and application in Buchwald-Hartwig cross coupling reaction

Wang, Fan; et al, Youji Huaxue, 2017, 37(8), 2050-2056

Production Method 3

623-12-1

85448-89-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Bis(dibenzylideneacetone)palladium ,  Phosphine, dicyclohexyl(2-phenyl-1H-inden-3-yl)-, tetrafluoroborate(1-) (1:1) Solvents: 1,2-Dimethoxyethane ;  15 h, 120 °C; 120 °C → rt

Reference

Preparation of anionic phosphine ligands in situ for the palladium-catalyzed Buchwald/Hartwig amination reactions of aryl halides

Chen, Lei; et al, Journal of Organometallic Chemistry, 2010, 695(14), 1768-1775

Production Method 4

1134-92-5

85448-89-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1,1-Bis(diphenylphosphino)ferrocene Solvents: Toluene ;  rt; 16 h, 105 °C

Reference

Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates

Ackermann, Lutz; et al, Organic Letters, 2011, 13(7), 1784-1786

Production Method 5

85448-89-1

Reaction Conditions

1.1 Catalysts: Palladium hydroxide Solvents: Toluene ;  30 min, rt
1.2 Reagents: Hydrogen ;  30 min, 0.2 MPa, rt → 140 °C
1.3 Reagents: Styrene ,  Tetradecane Solvents: Toluene ;  30 min, rt; 30 min, 0.5 MPa, 140 °C

Reference

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Ichitsuka, Tomohiro ; et al, Angewandte Chemie, 2020, 59(37), 15891-15896

Production Method 6

16419-60-6

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cupric acetate ;  1.5 h

Reference

Solvent-free N-arylation of amines with arylboronic acids under ball milling conditions

Zhu, Xingyi; et al, RSC Advances, 2014, 4(43), 22775-22778

Production Method 7

5416-93-3

85448-89-1

Reaction Conditions

1.1 4 h, 150 °C
2.1 Reagents: Methyl iodide Solvents: Xylene ;  3 h, 160 °C
3.1 Reagents: Aluminum chloride Solvents: Dimethylformamide ,  Nitrobenzene ;  1 h, 150 °C

Reference

Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

Barrera, Edson ; et al, European Journal of Organic Chemistry, 2022, 2022(24),

Production Method 8

2016028-94-5

1516-21-8

85448-89-1

605-39-0

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Toluene ;  12 h, 70 °C

Reference

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Li, Gang ; et al, Angewandte Chemie, 2021, 60(10), 5230-5234

Production Method 9

696-62-8

85448-89-1

119713-65-4

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Cuprous iodide Solvents: Toluene ;  14 h, 135 °C

Reference

Copper-catalyzed amination of aryl halides: single-step synthesis of triarylamines

Kelkar, Ashutosh A.; et al, Tetrahedron Letters, 2002, 43(40), 7143-7146

Production Method 10

615-37-2

85448-89-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Tris(dibenzylideneacetone)dipalladium ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Toluene

Reference

An Improved Method for the Palladium-Catalyzed Amination of Aryl Iodides

Ali, Mayssam H.; et al, Journal of Organic Chemistry, 2001, 66(8), 2560-2565

Production Method 11

615-37-2

85448-89-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Tris(dibenzylideneacetone)dipalladium Solvents: 1,4-Dioxane

Reference

A Diels-Alder approach to biaryl synthesis

Ashburn, Bradley O., 2008, , 69(3),

Production Method 12

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: (SP-4-1)-[1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-yliden… Solvents: 1,4-Dioxane ;  24 h, 110 °C

Reference

Synthesis of N-heterocyclic carbene-PdCl2-(iso)quinoline complexes and their application in arylamination at low catalyst loadings

Liu, Feng; et al, Organic & Biomolecular Chemistry, 2016, 14(8), 2563-2571

Production Method 13

623-12-1

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: 2102190-63-4 Solvents: Cyclopentyl methyl ether ;  1 h, 60 °C
1.2 Solvents: Cyclopentyl methyl ether ;  2 h, 80 °C

Reference

Palladate Precatalysts for the Formation of C-N and C-C Bonds

Zinser, Caroline M.; et al, Organometallics, 2019, 38(14), 2812-2817

Production Method 14

2839353-55-6

85448-89-1

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dimethylformamide ,  Nitrobenzene ;  1 h, 150 °C

Reference

Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

Barrera, Edson ; et al, European Journal of Organic Chemistry, 2022, 2022(24),

Production Method 15

5720-07-0

611-23-4

85448-89-1

Reaction Conditions

1.1 Catalysts: Cuprous chloride Solvents: Dimethylformamide ;  40 min, 55 °C
1.2 Solvents: Dimethylformamide ;  16 h, 55 °C

Reference

Cu(I)-Mediated Reductive Amination of Boronic Acids with Nitroso Aromatics

Yu, Ying; et al, Organic Letters, 2004, 6(15), 2631-2634

Production Method 16

85448-89-1

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Cuprous iodide ,  N1,N2-Bis(2-furanylmethyl)ethanediamide Solvents: Ethanol ;  24 h, 100 °C

Reference

N,N'-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines

Bhunia, Subhajit; et al, Journal of Organic Chemistry, 2017, 82(23), 12603-12612

Production Method 17

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Tris(dibenzylideneacetone)dipalladium ,  (+)-BINAP Solvents: Toluene ;  18 h, 90 °C

Reference

Photocatalytic Cross-Dehydrogenative Amination Reactions between Phenols and Diarylamines

Zhao, Yating; et al, ACS Catalysis, 2017, 7(4), 2446-2451

Production Method 18

85448-89-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide ,  (2S)-N-[4-(4-Phenyl-1H-1,2,3-triazol-1-yl)phenyl]-2-pyrrolidinecarboxamide Solvents: Water ;  24 h, 100 °C

Reference

"On Water'' Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

Chakraborti, Gargi; et al, Journal of Organic Chemistry, 2018, 83(14), 7347-7359

Production Method 19

16419-60-6

85448-89-1

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: 4,4′-Dimethyl-2,2′-bipyridine ,  Nickel, chloro(η5-2,4-cyclopentadien-1-yl)[rel-(3aR,9aR)-1,3-dicyclohexyl-1,3,3a… Solvents: Dimethylformamide ,  Toluene ;  rt; 8 h, 70 °C
1.2 Reagents: Water ;  rt

Reference

Nickel-catalyzed N-arylation of amines with arylboronic acids under open air

Ando, Shin ; et al, Tetrahedron Letters, 2019, 60(18), 1277-1280

Production Method 20

85448-89-1

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Catalysts: Nickel, [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bromo(2-methylphen… Solvents: Toluene ;  70 °C

Reference

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Li, Gang ; et al, Angewandte Chemie, 2021, 60(10), 5230-5234

Production Method 21

45713-46-0

85448-89-1

Reaction Conditions

1.1 Reagents: Acetic acid ,  Tempo Catalysts: Copper Solvents: Acetonitrile ;  250 psi, 40 °C

Reference

The solid copper-mediated C-N cross-coupling of phenylboronic acids under continuous flow conditions

Bao, Jennifer; et al, Tetrahedron Letters, 2016, 57(6), 654-657

Production Method 22

290357-55-0

85448-89-1

Reaction Conditions

1.1 Reagents: Methyl iodide Solvents: Xylene ;  3 h, 160 °C
2.1 Reagents: Aluminum chloride Solvents: Dimethylformamide ,  Nitrobenzene ;  1 h, 150 °C

Reference

Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

Barrera, Edson ; et al, European Journal of Organic Chemistry, 2022, 2022(24),

Production Method 23

192863-36-8

85448-89-1

605-39-0

Reaction Conditions

1.1 Reagents: Sodium nitrite Solvents: Heptane ,  Water ;  2 h, 50 °C
2.1 Reagents: Diisopropylethylamine Solvents: Toluene ;  12 h, 70 °C

Reference

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Li, Gang ; et al, Angewandte Chemie, 2021, 60(10), 5230-5234

Production Method 24

85448-89-1

605-39-0

Reaction Conditions

1.1 2 h, rt
2.1 Reagents: Diisopropylethylamine Solvents: Toluene ;  12 h, 70 °C

Reference

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Li, Gang ; et al, Angewandte Chemie, 2021, 60(10), 5230-5234

Production Method 25

72914-19-3

85448-89-1

605-39-0

Reaction Conditions

1.1 Reagents: Bis(1,5-cyclooctadiene)nickel Solvents: Tetrahydrofuran ;  4 h, rt
1.2 2 h, rt
2.1 Reagents: Diisopropylethylamine Solvents: Toluene ;  12 h, 70 °C

Reference

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Li, Gang ; et al, Angewandte Chemie, 2021, 60(10), 5230-5234

2'-Methyl-4-methoxydiphenylamine Raw materials

• 2-Iodotoluene
• 4-Methoxyphenyl isocyanate
• (4-methoxyphenyl)boronic acid
• (2-methylphenyl)boronic acid
• Sulfamic acid, N,N-dimethyl-, 2-methylphenyl ester
• Nickel, [4,4'-bis(1,1-dimethylethyl)-2,2'-bipyridine-κN1,κN1']bromo(2-methylphenyl)-, (SP-4-2)-
• Potassium (4-Methoxyphenyl)trifluoroborate
• 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine
• 1-chloro-4-methoxybenzene
• 4-Iodoanisole
• 7,7a-Dihydro-3-(4-methoxyphenyl)-7a-methyl-2(3H)-benzoxazolone
• 3-(4-Methoxyphenyl)-4,5-dimethyl-2(3H)-oxazolone
• 2-Nitrosotoluene
• (4-Methoxyphenyl)boronic acid
• Benzene,1-methoxy-4-nitroso-

2'-Methyl-4-methoxydiphenylamine Preparation Products

• Benzenamine, N,N-bis(4-methoxyphenyl)-2-methyl- (119713-65-4)
• 2'-Methyl-4-methoxydiphenylamine (85448-89-1)
• 2,2'-Dimethylbiphenyl (605-39-0)

• 1. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 2. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 3. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 4. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 5. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527

• 41317-15-1(4-Methoxy-2-methyldiphenylamine)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)