Production Method 1

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Iron hydroxide oxide Solvents: Ethanol ,  Water ;  5 h, 75 °C

Reference

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

Li, Dingzhong; Lu, Hao; Yang, Tianbao; Xing, Chen; Sun, Tulai; et al, Catalysis Communications, 2022, 162,

Production Method 2

2887929-43-1

95-81-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cupric acetate Solvents: Ethanol ;  8 - 12 h, 100 °C

Reference

Exploration of Copper(II) Acetate Catalyzed Regioselective Ethoxylation of o-Haloanilides with Picolinamide as a Directing Group

Li, Xiaoyi; Qin, Dingmei; Li, Yanping; Mao, Zewei, Synlett, 2023, 34(3), 253-258

Production Method 3

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Platinum Solvents: Water ;  2 - 3 h, 25 °C

Reference

Immobilization of platinum nanoparticles on the functionalized chitosan particles: an efficient catalyst for reduction of nitro compounds and tandem reductive Ugi reactions

Hamzavi, Seyedeh Fazileh; Jamili, Shahla; Yousefzadi, Morteza; Mashinchian Moradi, Ali; Amrollahi Biuki, Narges, Molecular Diversity, 2020, 24(4), 985-995

Production Method 4

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Cobalt sulfate (CoSO4) heptahydrate ,  Sodium borohydride Solvents: Ethanol ,  Water ;  0 °C; 10 min, rt
1.2 Reagents: Water ;  rt

Reference

A Co2B Mediated NaBH4 Reduction Protocol Applicable to a Selection of Functional Groups in Organic Synthesis

Lundevall, Frida Johanne; Elumalai, Vijayaragavan ; Drageset, Audun; Totland, Christian; Bjorsvik, Hans-Rene, European Journal of Organic Chemistry, 2018, 2018(26), 3416-3425

Production Method 5

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Carbon Solvents: Ethanol ;  2 h, 90 °C

Reference

N,S co-doped hierarchically porous carbon materials for efficient metal-free catalysis

Hu, Xiwei; Sun, Xun; Song, Qiang; Zhu, Yangyang; Long, Yu; et al, Green Chemistry, 2020, 22(3), 742-752

Production Method 6

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Iron Solvents: Acetic acid ;  30 min, rt → 90 °C

Reference

Synthesis and antileishmanial evaluation of thiazole orange analogs

Abdelhameed, Ahmed; Liao, Xiaoping; McElroy, Craig A.; Joice, April C.; Rakotondraibe, Liva; et al, Bioorganic & Medicinal Chemistry Letters, 2020, 30(1),

Production Method 7

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Synthesis of 4-halotoluene-2- and 3-sulfonic acids, and sulfonation mixtures of 4-halotoluenes by the HPLC (high performance liquid chromatography) analysis

Muramoto, Yoshirio; Asakura, Hideyuki; Suzuki, Hitomi, Kinki Daigaku Kogakubu Kenkyu Hokoku, 1991, 25, 73-9

Production Method 8

95-81-8

Reaction Conditions

Reference

Process for preparing 4,5-difluorobenzaldehydes from chlorofluorobenzaldehydes

, European Patent Organization, , ,

Production Method 9

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Nickel ,  Carbon Solvents: Methanol ,  Water ;  4 h, 2 MPa, 100 °C

Reference

Nickel Nanoparticles Encapsulated in Carbon Nanotubes as an Efficient and Robust Catalyst for Hydrogenation of Nitroarenes

Ding, Shunmin; Cheng, Dan; Xiao, Weiming; Ma, Xiaohua; Zeng, Rong; et al, Catalysis Letters, 2023, 153(2), 595-604

Production Method 10

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Iron hydroxide oxide Solvents: Ethanol ;  60 - 70 °C

Reference

Green preparation of carbon-supported iron-based catalyst and its application in synthesis of anticancer inhibitor intermediates

, World Intellectual Property Organization, , ,

Production Method 11

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Iron ,  Hydrochloric acid ,  Ammonium chloride Solvents: Water ;  1.5 h, rt → reflux
1.2 reflux; 3 h, reflux
1.3 Reagents: Sodium carbonate Solvents: Water ;  pH 9 - 10

Reference

Synthesis of 4-chloro-3-fluorotoluene and 4-bromo-3-fluorotoluene

Zhao, Haoyu; Xue, Xuming; Jiang, Tao, Jingxi Shiyou Huagong, 2007, 24(1), 39-43

Production Method 12

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Sodium dithionite

Reference

Alkaline Soil Degradation and Crop Safety of 5-Substituted Chlorsulfuron Derivatives

Wu, Lei ; Hua, Xue-Wen; Li, Yong-Hong; Wang, Zhong-Wen; Zhou, Sha; et al, Molecules, 2022, 27(10),

Production Method 13

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Carbon Solvents: Methanol ,  Water ;  3 h, 5 bar, 90 °C

Reference

Co,N-Codoped Porous Carbon-Supported CoyZnS with Superior Activity for Nitroarene Hydrogenation

Zhang, Guangji; Tang, Feiying; Wang, Xiaoying; An, Ping; Wang, Liqiang ; et al, ACS Sustainable Chemistry & Engineering, 2020, 8(15), 6118-6126

Production Method 14

89-60-1

95-81-8

Reaction Conditions

1.1 Catalysts: Cobalt (reaction products with 2-methylimidazole, m-aminophenol, formaldehyde Mesoporous Yolk-shell supported) Solvents: Ethanol ;  5 min, 80 °C
1.2 Reagents: Hydrazine hydrate (1:1) ;  10 min, 80 °C

Reference

Co-MOF-derived Hierarchical Mesoporous Yolk-shell-structured Nanoreactor for the Catalytic Reduction of Nitroarenes with Hydrazine Hydrate

Yuan, Man; Zhang, Hongbo; Yang, Chen; Wang, Fanhao; Dong, Zhengping, ChemCatChem, 2019, 11(14), 3327-3338

Production Method 15

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Cyanuric chloride-piperazine copolymer Solvents: Ethanol ,  Water ;  3.5 h, 100 °C

Reference

Two-dimensional covalent organic frameworks as self-template derived nitrogen-doped carbon nanosheets for eco-friendly metal-free catalysis

Hu, Xiwei; Long, Yu; Fan, Mengying; Yuan, Man; Zhao, Hong; et al, Applied Catalysis, 2019, 244, 25-35

Production Method 16

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Palladium (reaction product with porous organic polymer) ,  Cyanuric chloride-piperazine copolymer Solvents: Ethanol ,  Water ;  15 min, 25 °C

Reference

Ultra-fine Pd nanoparticles confined in a porous organic polymer: A leaching-and-aggregation-resistant catalyst for the efficient reduction of nitroarenes by NaBH4

Yuan, Man; Yang, Renzi; Wei, Shuoyun; Hu, Xiwei; Xu, Dan; et al, Journal of Colloid and Interface Science, 2019, 538, 720-730

Production Method 17

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Palladium (aminal-based hypercrosslinked polymer supported) ,  Ferrocene, formyl-, polymer with 1,3,5-triazine-2,4,6-triamine Solvents: Ethanol ,  Water ;  15 min, rt

Reference

Aminal-based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Xu, Dan; Wang, Fushan; Yu, Guiqin; Zhao, Hong; Yang, Jing; et al, ChemCatChem, 2018, 10(20), 4569-4577

Production Method 18

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Iron ,  Hydrochloric acid Solvents: Methanol ,  Water ;  2 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  basified

Reference

Preparation of tricyclic compounds as mPGES-1 inhibitors

, World Intellectual Property Organization, , ,

Production Method 19

89-60-1

95-81-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Stannous chloride Solvents: Ethanol ,  Water ;  70 min, 60 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 12

Reference

Substituted tetrahydro-1H-pyrido[4,3-b]indoles as serotonin receptors agonists and antagonists for treating metabolic, CNS, and gastrointestinal disorders

, United States, , ,

2-Chloro-5-methylaniline Raw materials

• 4-Chloro-3-nitrotoluene
• N-(2-Chloro-5-methylphenyl)-2-pyridinecarboxamide

2-Chloro-5-methylaniline Preparation Products

• 2-Chloro-5-methylaniline (95-81-8)

• 1. An atlas of endohedral Sc2S cluster fullerenes?
  Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. Fowler Phys. Chem. Chem. Phys., 2017,19, 419-425
• 2. Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties?
  S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. Lee RSC Adv., 2014,4, 23107-23115
• 3. An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands?
  Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier Felpin React. Chem. Eng., 2019,4, 1608-1615
• 4. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 5. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877

• 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

• 5307-03-9(2-Chloro-5-methyl-1,4-phenylenediamine)
• 62224-71-9(Benzenamine, 2-chloro-5-methyl-, hydrochloride)
• 5400-76-0(Benzenamine,2,4,6-trichloro-3-methyl-)
• 34207-43-7(1,3-Benzenediamine, 2-chloro-5-methyl-)
• 615-65-6(2-Chloro-4-methylaniline)
• 56461-98-4(2,6-Dichloro-4-methylaniline)
• 19853-79-3((2,4-Dichloro-3-methylphenyl)amine Hydrochloride)
• 17601-75-1(2,4-Dichloro-5-methylaniline)
• 29027-17-6(2-Chloro-3-methylaniline)
• 102677-74-7(5-(Aminomethyl)-2-chloroaniline dihydrochloride)