1205-40-9

Basic information

• Product Name: (2-CHLORO-PHENYL)-PHENYL-AMINE
• Synonyms: (2-CHLORO-PHENYL)-PHENYL-AMINE;2-Chlorodiphenylamine;N-(2-Chlorophenyl)benzenamine;2-Chloro-N-phenylaniline;BenzenaMine, 2-chloro-N-phenyl-;N-(2-chlorophenyl)aniline
• CAS NO: 1205-40-9
• Molecular Formula: C₁₂H₁₀ClN
• Molecular Weight: 203.6675
• Mol File: 1205-40-9.mol

Chemical Properties

• Melting Point: 100-101℃
• Boiling Point: 304 °C at 760 mmHg
• Flash Point: 137.6 °C
• Appearance: /
• Density: 1.216±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000899mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -0.90±0.20(Predicted)
• CAS DataBase Reference: (2-CHLORO-PHENYL)-PHENYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-CHLORO-PHENYL)-PHENYL-AMINE(1205-40-9)
• EPA Substance Registry System: (2-CHLORO-PHENYL)-PHENYL-AMINE(1205-40-9)

Safety Data

• Hazardous Substances Data: 1205-40-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
(2-CHLORO-PHENYL)-PHENYL-AMINE is used as a key intermediate in the production of dyes, pharmaceuticals, and other organic compounds. Its unique structure allows for further chemical reactions to create a wide range of products.
Used in Dye Manufacturing:
(2-CHLORO-PHENYL)-PHENYL-AMINE is used as a precursor in the synthesis of various dyes. Its presence in the molecular structure contributes to the color and properties of the final dye product.
Used in Pharmaceutical Industry:
(2-CHLORO-PHENYL)-PHENYL-AMINE is used as a building block in the development of pharmaceuticals. Its chemical properties enable it to be incorporated into drug molecules, potentially leading to new treatments and therapies.
Safety Considerations:
Due to its potential for causing skin and eye irritation, as well as being harmful if ingested or inhaled, (2-CHLORO-PHENYL)-PHENYL-AMINE is considered a hazardous substance. It is crucial to follow proper safety protocols when handling this chemical to minimize potential health risks.

InChI:InChI=1/C12H10ClN/c13-11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H

Upstream product

• 108-90-7 chlorobenzene 
• 622-37-7 Phenyl azide 
• 299192-77-1 (N-phenyl)(benzyliden)(o-chlorophenoxy)imine 
• 591-50-4 iodobenzene 
• 95-51-2 o-chloroaniline 
• 100-63-0 phenylhydrazine 
• 62-53-3 aniline 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 95-50-1 1,2-dichloro-benzene 
• 122-39-4 diphenylamine 
• 615-41-8 2-iodochlorobenzene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 876120-45-5 C₁₅H₁₄ClNO₂ 
• 108-86-1 bromobenzene 

Downstream Products

• 129574-31-8 N-(2-chlorophenyl)-4-chloro-3-methyl-2(1H)-quinolone 
• 86-74-8 9H-carbazole 
• 122-39-4 diphenylamine 
• 16176-77-5 2-methyl-1-phenyl-1H-indole 
• 1484-12-4 N-methylcarbazole 
• 299192-72-6 2-chloro-2-thiono-1,3-bisphenyl-2,3-dihydro-1,3,2-benzodiazaphosphole 
• 28510-57-8 N,N'-bisphenyl-N-benzoyl-o-phenylenediamine 
• 28394-83-4 N,N'-diphenyl-o-phenylenediamine 
• 131706-16-6 N-(phenyl)(N'-phenyl)[N'-(o-chloro)phenyl]carboxamidine 
• 129574-37-4 N-(2-chlorophenyl)-4-hydroxy-3-methyl-2(1H)-quinolone 
• 131706-16-6 N-(2-chloro-phenyl)-N,N'-diphenyl-benzamidine 
• 1910-85-6 1-chlorophenothiazine 

Relevant articles and documents

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica

The construction of C?N bonds with nitroaromatics and boronic acids using highly efficient and recyclable catalysts remains a challenge. In this study, nanoporous MoO3 confined in silica serves as an efficient heterogeneous catalyst for C?N cross-coupling of nitroaromatics with aryl or alkyl boronic acids to deliver N-arylamines and with desirable multiple reusability. Experimental results suggest that silica not only heterogenizes the Mo species in the confined mesoporous microenvironment but also significantly reduces the reaction induction period and regulates the chemical efficiency of the targeted product. The well-shaped MoO3@m?SiO2 catalyst exhibits improved catalytic performance both in yield and turnover number, in contrast with homogeneous Mo catalysts, commercial Pd/C, or MoO3 nanoparticles. This approach offers a new avenue for the heterogeneous catalytic synthesis of valuable bioactive molecules.

A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C-N coupling reaction

A novel porous organic polymer (denoted by Q-POP) was successfully fabricated by free-radical copolymerization of allyl-substituted 2,3-di(2-hydroxyphenyl)1,2-dihydroquinoxaline, and divinylbenzene under solvothermal conditions and used as a new platform for immobilization of copper nanoparticles. The CuNPs@Q-POP nanocatalyst was prepared via incorporating of Cu(NO3)2 into the polymeric network, followed by the reduction of Cu2+ ion with hydrazine hydrate. The obtained materials were characterized through FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and the single-crystal X-ray crystallography. The results displayed that Q-POP and CuNPs@Q-POP possessed high surface area, hierarchical porosity, and excellent thermal and chemical stability. The as-synthesized catalyst was utilized for the Ullmann C-N coupling reaction of aromatic amines and different aryl halides to prepare various diarylamine derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C-N coupling reaction with aromatic amines to produce diaryl amines in good to excellent yields (50-98%), and it turned out that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss.

Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling

Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is

Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines

Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.

Reductive Molybdenum-Catalyzed Direct Amination of Boronic Acids with Nitro Compounds

The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C?N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. Moreover, this general and step-economical synthesis of aromatic secondary amines showcases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.

Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines

A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou

Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines

A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou