Production Method 1

58532-75-5

858516-23-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Dimethyl sulfoxide ;  2 h, 50 °C
1.2 Reagents: Potassium hydroxide ;  2 h, 130 °C

Reference

Direct amination of phenols under metal-free conditions

Yu, Jianzhong; et al, Synlett, 2013, 24(11), 1448-1454

Production Method 2

5720-05-8

858516-23-1

Reaction Conditions

1.1 Catalysts: Copper Solvents: Methanol ,  Water ;  8 h, rt

Reference

Copper immobilized at a covalent organic framework: an efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines

Han, Yi; et al, Green Chemistry, 2018, 20(21), 4891-4900

Production Method 3

5720-05-8

858516-23-1

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: 2113670-81-6 Solvents: Dichloromethane ;  12 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Sulfonato-diketimine Copper(II) Complexes: Synthesis and Application as Catalysts in Chan-Evans-Lam Couplings

Hardouin Duparc, Valerie; et al, Organometallics, 2017, 36(16), 3053-3060

Production Method 4

106-37-6

858516-23-1

Reaction Conditions

1.1 Reagents: Potassium fluoride Catalysts: Tris(dibenzylideneacetone)dipalladium ,  BINAP ;  15 min, 80 - 90 °C
1.2 1 h, 80 - 90 °C

Reference

Palladium-catalyzed selective amination of haloaromatics on KF-alumina surface

Basu, Basudeb; et al, Synlett, 2005, (8), 1275-1278

Production Method 5

66117-64-4

858516-23-1

Reaction Conditions

1.1 Reagents: Pyridine Catalysts: Cupric acetate Solvents: Dichloromethane ;  24 h, rt

Reference

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids

Guan, Changwei; et al, Tetrahedron, 2017, 73(49), 6906-6913

Production Method 6

87261-59-4

858516-23-1

Reaction Conditions

1.1 Catalysts: Copper diacetate monohydrate ,  Tetramethylguanidinium acetate ;  8 h, 60 - 65 °C

Reference

Copper Catalyzed N-Arylation of Amines in Ionic Liquid Using 1-Aryltriazenes as Aryl Surrogates

Kim, Kang M.; et al, ChemistrySelect, 2021, 6(11), 2709-2715

Production Method 7

858516-23-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 - 5 °C; 15 min, 0 - 5 °C
1.2 Reagents: Potassium hydroxide Solvents: Water ;  30 min, 0 - 5 °C
2.1 Catalysts: Copper diacetate monohydrate ,  Tetramethylguanidinium acetate ;  8 h, 60 - 65 °C

Reference

Copper Catalyzed N-Arylation of Amines in Ionic Liquid Using 1-Aryltriazenes as Aryl Surrogates

Kim, Kang M.; et al, ChemistrySelect, 2021, 6(11), 2709-2715

Production Method 8

5467-74-3

858516-23-1

Reaction Conditions

1.1 Catalysts: Copper Solvents: Methanol ,  Water ;  10 h, rt

Reference

Copper immobilized at a covalent organic framework: an efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines

Han, Yi; et al, Green Chemistry, 2018, 20(21), 4891-4900

Production Method 9

1014716-86-9

858516-23-1

Reaction Conditions

1.1 Catalysts: Cupric acetate Solvents: Toluene ;  5 min, rt
1.2 Reagents: Trimethylamine oxide ;  20 h, rt

Reference

Aryl triolborates: Novel reagent for copper-catalyzed N-arylation of amines, anilines, and imidazoles

Yu, Xiao-Qiang; et al, Chemistry - An Asian Journal, 2008, 3(8-9), 1517-1522

Production Method 10

589-87-7

858516-23-1

Reaction Conditions

1.1 Reagents: 2-Phenyl-1,3,2-dioxaborinane ,  Tripotassium phosphate Catalysts: Bis(acetylacetonato)nickel Solvents: 1,4-Dioxane ;  24 h, 115 °C

Reference

Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald-Hartwig-Type Amination toward Bioactivity Assay

Dhital, Raghu N.; et al, ACS Omega, 2022, 7(28), 24184-24189

Production Method 11

589-87-7

858516-23-1

Reaction Conditions

Reference

Palladium-catalyzed Selective Amination of Aryl(haloaryl)amines with 9H-Carbazole Derivatives

Ohtsuka, Yuhki; et al, Advanced Synthesis & Catalysis, 2018, 360(5), 1007-1018

Production Method 12

46449-56-3

37181-39-8

858516-23-1

Reaction Conditions

1.1 Reagents: Sodium carbonate ,  Silica Catalysts: Cuprous iodide ;  20 min

Reference

Mechanically Induced N-arylation of Amines with Diaryliodonium Salts

Jiang, Jun; et al, ChemistrySelect, 2020, 5(2), 542-548

Production Method 13

5467-74-3

858516-23-1

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Trimethylsilyl-terminated polymethylsiloxane Catalysts: Aniline ,  Molybdenum ,  Basolite Z 1200 Solvents: Toluene ;  12 h, 120 °C

Reference

Highly dispersed, subnano Mo-catalyzed reductive C-N coupling of aryl boric acids and aromatic nitro compounds

Zhu, Yanfang; et al, Tetrahedron, 2023, 139,

Production Method 14

5467-74-3

858516-23-1

Reaction Conditions

1.1 Reagents: Triethyl phosphite ,  Tetrabutylammonium tetrafluoroborate Solvents: Formic acid ,  Acetonitrile ,  1,1,1,3,3,3-Hexafluoro-2-propanol ;  3 h, rt

Reference

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids

Wang, Dan; et al, ChemSusChem, 2021, 14(24), 5399-5404

Production Method 15

474661-35-3

858516-23-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: 1,1′-[2-[(Diphenylphosphino)methyl]-2-methyl-1,3-propanediyl]bis[1,1-diphenylpho… ,  Methanesulfonic acid, 1,1,1-trifluoro-, nickel(2+) salt (2:1) Solvents: 2,2,2-Trifluoroethanol ;  16 h, 40 bar, 100 °C

Reference

Nickel-catalyzed hydrogenative coupling of nitriles and amines for general amine synthesis

Chandrashekhar, Vishwas G. ; et al, Science (Washington, 2022, 376(6600), 1433-1441

Production Method 16

106-39-8

858516-23-1

620-91-7

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  (T-4)-[1,1′-Bis(diphenylphosphino-κP)ferrocene]bis(triphenyl phosphite-κP)nickel Solvents: Toluene ;  22 h, 60 °C; cooled
1.2 Reagents: Hydrogen peroxide Solvents: Water ;  2 h, cooled

Reference

Stable nickel(0) phosphites as catalysts for C-N cross-coupling reactions

Kampmann, Sven S.; et al, Advanced Synthesis & Catalysis, 2014, 356(9), 1967-1973

4-Bromo-N-(p-tolyl)aniline Raw materials

• (4-bromophenyl)boronic acid
• 1,4-Dibromobenzene
• 4-Chlorobromobenzene
• 2-Bromo-N-(4-methylphenyl)propanamide
• Borate(1-), [2-[(hydroxy-O)methyl]-2-methyl-1,3-propanediolato(3-)-O1,O3](4-methylphenyl)-, potassium (1:1), (T-4)-
• 1-Bromo-4-iodobenzene
• 4-Methylbenzeneboronic Acid
• Toliodium
• Hydroxydi-p-tolylborane
• Piperidine, 1-[(4-bromophenyl)azo]-

4-Bromo-N-(p-tolyl)aniline Preparation Products

• 4-Bromo-N-(p-tolyl)aniline (858516-23-1)
• N1,N4-Di-p-tolylbenzene-1,4-diamine (620-91-7)

• 1. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
• 2. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 3. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312
• 4. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 5. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aminotoluenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes Aminotoluenes

• 54446-36-5(4-Bromo-N-phenylaniline)
• 183798-74-5(Benzenamine, 4-bromo-N-(4-methylphenyl)-N-phenyl-)
• 585570-08-7(n,n'-bis(4-bromophenyl)benzidine)
• 499128-71-1(N,N-Bis(4-biphenylyl)-N-(4-bromophenyl)amine)
• 202831-65-0(4'-Bromo-N,N-diphenyl-1,1'-biphenyl-4-amine)
• 58047-42-0(4-Bromo-4’,4”-dimethyltriphenylamine)
• 344782-48-5(N4,N4'-Bis(4-bromophenyl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine)
• 668493-37-6([1,1':4',1''-Terphenyl]-4-amine, 4''-bromo-N,N-diphenyl-)
• 16292-17-4(Bis(4-bromophenyl)amine)
• 884530-69-2(4,4'-Dibromo-4''-phenyltriphenylamine)