615-66-7

Basic information

• Product Name: 2-Chloro-1,4-diaminobenzene
• Synonyms: O-CHLORO-P-PHENYLENE DIAMINE;TIMTEC-BB SBB007575;1,4-diamino-2-chlorobenzene;2-chloro-1,4-benzenediamine;2-chloro-4-benzenediamine;2-chloro-p-phenylenediamin;2-chlor-p-fenylendiamin;3-chloro-4-aminoaniline
• CAS NO: 615-66-7
• Molecular Formula: C₆H₇ClN₂
• Molecular Weight: 142.59
• EINECS: 210-441-2
• Product Categories: Intermediates of Dyes and Pigments;pharmacetical
• Mol File: 615-66-7.mol

Chemical Properties

• Melting Point: 62-66 °C
• Boiling Point: 232.49°C (rough estimate)
• Flash Point: 127.9 °C
• Appearance: /
• Density: 1.2124 (rough estimate)
• Vapor Pressure: 0.00242mmHg at 25°C
• Refractive Index: 1.5210 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO, Methanol (Slightly)
• PKA: 4.80±0.10(Predicted)
• Water Solubility: 49.61g/L at 25℃
• CAS DataBase Reference: 2-Chloro-1,4-diaminobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,4-diaminobenzene(615-66-7)
• EPA Substance Registry System: 2-Chloro-1,4-diaminobenzene(615-66-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SS8925000
• Hazardous Substances Data: 615-66-7(Hazardous Substances Data)

Usage

Uses

Used in Hair Dye Formulations:
2-Chloro-1,4-diaminobenzene is used as an intermediate in the production of hair dye formulations. Its chemical structure allows it to react with other components in the formulation, resulting in the formation of colored compounds that can effectively color hair. 2-Chloro-1,4-diaminobenzene's reactivity and stability make it a valuable ingredient in the hair dye industry.
Used in Chemical Synthesis:
In the chemical industry, 2-Chloro-1,4-diaminobenzene is used as a building block for the synthesis of various organic compounds. Its unique structure and reactivity enable the creation of a wide range of products, including pharmaceuticals, dyes, and other specialty chemicals. 2-Chloro-1,4-diaminobenzene's versatility in chemical reactions makes it an essential component in the synthesis of complex molecules.
Used in Research and Development:
Due to its unique chemical properties, 2-Chloro-1,4-diaminobenzene is also utilized in research and development for the study of various chemical reactions and processes. It serves as a model compound for understanding the behavior of similar molecules and can be used to develop new synthetic methods and techniques in organic chemistry.

Production Methods

The compound is used in hair dye formulations. 2-Chloro-p- PDA sulfate was mutagenic in the Ames test.

Flammability and Explosibility

Nonflammable

Safety Profile

An experimental teratogen. Other experimental reproductive effects. An eye irritant. Decomposes explosively at 165℃/33 mbar. When heated to decomposition it emits toxic fumes of Cl and NOx. See also AROMATIC MINES.

Carcinogenicity

2-Chloro-1,4-diaminobenzene was not carcinogenic in rats or mice in 2-year feeding studies. No new information was located.

InChI:InChI=1/C6H7ClN2.H2O4S/c7-5-3-4(8)1-2-6(5)9;1-5(2,3)4/h1-3H,8-9H2;(H2,1,2,3,4)

Upstream product

• 36164-93-9 chloro-[1,4]benzoquinone dioxime 
• 121-87-9 2-Chloro-4-nitroaniline 
• 3874-84-8 2-amino-5-sulhpoamoylnaphthalene-azo-(2'-chloro-4'-nitrobenzene) 
• 7647-01-0 hydrogenchloride 
• 86119-84-8 phosphoric acid 
• 116106-30-0 cyclohexane-1,4-dione-dioxim; hydrochloride 
• 64-17-5 ethanol 
• 13362-35-1 2-chloro-1,4-benzoquinone-4-oxime 
• 38762-41-3 2-chloro-4-bromoaniline 
• 825-41-2 3-chloro-4-nitroaniline 
• 619-16-9 1-chloro-2,5-dinitrobenzene 

Downstream Products

• 90932-84-6 chloro-[1,4]benzoquinone-bis-bromoimine 
• 66608-29-5 2-Chlor-N,N'-bis-(N-diethoxyphosphoryl-thiocarbamoyl)-1,4-phenylendiamin 
• 82003-25-6 2-chloro-N,N'-bisphenylthio-benzoquinone diimide 
• 695-99-8 2-Chloro-1,4-benzoquinone 
• 711597-89-6 2,4-dinitro-2'-chloro-4'-aminodiphenylamine-6-sulfonic acid 
• 1241381-22-5 1,12-(2-chloro-1,4-phenylene)bis(1H-tetrazole) 
• 300360-38-7 N,N'-(chloro-p-phenylene)-bis-benzamide 
• 98763-13-4 N,N′-(2-chlorocyclohexa-2,5-diene-1,4-diylidene)bis(4-chlorobenzenesulfonamide) 
• 10558-45-9 N-(4-amino-2-chloro-phenyl)-5-chloro-2-hydroxy-benzamide 
• 916052-53-4 tert-butyl (4-amino-3-chlorophenyl)carbamate 
• 951-06-4 5-methoxy-[4,7]phenanthroline 
• 3029-59-2 chloro-[1,4]benzoquinone-bis-chlorimin 

Relevant articles and documents

Ni-W2C/mpg-C3N4 as a promising catalyst for selective hydrogenation of nitroarenes to corresponding aryl amines in the presence of Lewis acid

The selective hydrogenation of nitroarenes to their corresponding aryl amines has been investigated over the supported nickel propoted tungsten carbide catalyst on polymeric mesoporous graphitic carbon nitride (Ni-W2C/mpg-C3N4) in the presence of Lewis acid. The Ni-W2C/mpg-C3N4 is demonstrated much higher catalytic activity and selectivity for the selective hydrogenation of nitrobenzene than the supported Ni-W2C catalyst on activated carbon (Ni-W2C/AC) and mesoporous carbon (Ni-W2C/CMK-3), and the developed Ni-W2C/mpg-C3N4 also exhibits excellent catalytic properties for the selective hydrogenation of various substrates comprising the extra reducible functionalized groups besides nitro group to diverse functionalized arylamines, industrially important compounds, offering more than 92% of yield with 100% selectivity, which may be ascribed to the strengthened mass transfer by using mesoporous support, intentified synergistic effect between Ni-W2C/mpg-C3N4 and Lewis acid owing to the basicity of mpg-C3N4, as well as the improved reducibility of NiO-WO3 and the dispersion of Ni-W2C. It can be also found that the developed catalyst could be easily recovered by filtration and recycled many times without visible loss in its catalytic performance. The significantly improved catalytic properties of supported Ni-W2C catalyst fabricated by using mpg-C3N4 as a superior carrier in the presence of Lewis acid allows it to be a promising candidate for the clean and highly-efficient synthesis of diverse functionalized arylamines through the selectivie hydrogenation of substituted nitroarenes.

Highly efficient N-doped carbon supported FeSx-Fe2O3 catalyst for hydrogenation of nitroarenes via pyrolysis of sulfurized N,Fe-containing MOFs

Integrating MOFs as precursor, especially for employing N-containing organic linkers, with sulfides is an effective method to prepare the highly efficient N-doped carbon supported metal-based catalysts for hydrogenation of nitroarenes. In this work, a N,Fe-containing metal organic frameworks (MOFs; termed as MIL88-HMTA) with spindle-like structure was prepared via self-assembly method, in which hexamethylenetetramine (HMTA) linker was introduced as N source. Subsequently, N-doped carbon supported FeSx-Fe2O3 catalyst (named FeSx-Fe2O3@CN) was fabricated upon the pyrolysis of sulfurized MIL88-HMTA. Catalytic experiments reveal that the FeSx-Fe2O3@CN delivered excellent performance for hydrogenation of nitroarenes in comparison with those of catalyst without sulfidation process (Fe2O3@CN) and conventional MIL88 derived catalyst (Fe2O3@C). The XRD, TEM, SEM/EDX, Raman, UV, and XPS analyses have revealed that the developed FeSx-Fe2O3@CN catalyst exhibited outstanding catalytic efficiency was ascribed to synergistic effect between FeSx and Fe2O3 species, abundant structural defects, more Fe-Nx species, and strengthened decomposition ability of hydrazine hydrate (N2H4?H2O). Furthermore, the effect of sulfidation ratio (the mass ratio between thioacetamide and MIL88-HMTA) towards preparation of the developed FeSx-Fe2O3@CN on the catalytic activity of hydrogenation reaction was also systematically performed. Notably, the optimized catalyst (denoted as FeSx-Fe2O3@CN-8) exhibited unexpected performance and recyclability for hydrogenation of nitroarenes under mild condition. The pyrolysis of sulfurized N-containing MOFs may present a facile approach for fabricating MOFs-derived N-doped carbon supported catalysts, which provides a potential application in heterogeneous catalytic reactions.

A highly efficient LaOCl supported Fe-Fe3C-based catalyst for hydrogenation of nitroarenes fabricated by coordination-assisted pyrolysis

Bi-metal-organic framework (bi-MOF) derived carbon-based catalysts have exhibited considerable potential for hydrogenation reactions; however, designing suitable bi-MOFs to fabricate highly efficient catalysts is still a great challenge. Herein, an efficient LaOCl supported Fe-Fe3C-based carbon-nitrogen catalyst (Fe-Fe3C-LaOCl/CN-hmta) was first prepared by bi-MOF (La-salenFe@HMTA)-templated pyrolysis. La-salenFe@HMTAwas synthesizedviathe coordination-assisted method,e.g., it is prepared by the coordination of N from the rich free imine (-CHN-) groups located on the La-salen complex to the Fe3+ions from Fe@HMTA. Catalytic experiments reveal that Fe-Fe3C-LaOCl/CN-hmta as a hydrogenation catalyst exhibits excellent performance for hydrogenation of nitroarenes in comparison with catalysts derived from Fe-urea MOFs (Fe-Fe3C-LaOCl/CN-urea) and Fe(NO3)3·9H2O derived catalysts (Fe-Fe3C-LaOCl/CN). On the basis of the nature of Fe-Fe3C-LaOCl/CN-hmta and the reaction results, it is concluded that the unique catalytic efficiency of Fe-Fe3C-LaOCl/CN-hmta depends significantly on the synergistic effect of Fe and Fe3C, large specific surface area and abundant structural defects. This piece of research provides a new approach for preparing highly efficient and stable Fe-Fe3C-based catalysts for hydrogenation of nitroarenesviathe coordination-assisted pyrolysis (CAP) method.

Synthesis method of chloro-p-phenylenediamine

The invention discloses a synthesis method of chloro-p-phenylenediamine. The synthesis method sequentially comprises the following steps: o-chloro-p-nitroaniline, metal alkoxide and alcohol as a solvent are added to a reactor to be mixed, and the mixture is heated to 100-190 DEG C for a reaction for 2-6 h; a reaction product is cooled to room temperature, the alcohol solvent in a reaction liquid is recovered by distillation, and a remainder after recovery of the alcohol solvent is a crude product of chloro-p-phenylenediamine. The chloro-p-phenylenediamine is synthesized with the method, so that an expensive catalyst is not used, the process is simple, few three wastes are caused, and the method has good industrial application values.

Mechanochemical catalytic transfer hydrogenation of aromatic nitro derivatives

Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.

Unravelling 2-aminoquinazolin-4(3: H)-one as an organocatalyst for the chemoselective reduction of nitroarenes

A novel, mild and transition metal-free, 2-aminoquinazolin-4(3H)-one-assisted reduction of nitroarenes employing hydrazine hydrate as reducing agent and potassium carbonate as a base is reported. For the first time, the activation of hydrazine hydrate with an organocatalyst has been explored for reduction reactions. Also for the first time, 2-aminoquinazolin-4(3H)-one and its derivatives have been investigated as hydrogen bonding organocatalysts for the reduction of nitroarenes to anilines. Sensitive functional groups such as sulfonamide, carboxyl, amide and halides were well tolerated in this green methodology with scalability and high chemoselectivity.

Gold nanoparticles anchored onto the magnetic poly(ionic-liquid) polymer as robust and recoverable catalyst for reduction of Nitroarenes

Gold nanoparticles supported on poly ionic-liquid magnetic nanoparticles (MNP@PIL@Au) were synthesized by reduction of HAuCl4 with sodium borohydride. The synthesized catalyst was characterized using by AAS, TEM, FT-IR, EDS, TGA and XRD techniques. The performance of the synthesized catalyst was investigated in the reduction of nitroarenes with NaBH4. The reaction was carried out for various nitroarenes in water and mild conditions with high yields. The catalyst selectivity for the reduction of nitro group in the presences of other functional groups such as halides and alkynes was fairly well. The recycling of the catalyst was done 8 times without any significant loss of its catalytic activity.

A 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines (by machine translation)

The invention discloses a 4, 4 - dimethoxy - 2, 2 - bipyridyl silver catalytic hydrogenation of aromatic nitro compound synthesis of aromatic amines, the method uses a cheap, easy synthesis of 4, 4 - dimethoxy - 2, 2 - bipyridyl silver as catalyst, in order to green, environmental protection, non-toxic as the hydrogen source, the aromatic nitro compound in the relatively mild reaction conditions, one-step reaction can synthesize aromatic amine. The invention has simple operation, catalyst is cheap and easy and small consumption, mild reaction conditions, to substrate demonstrates better functional group tolerant, high product yield, industrial manufacturing cost, it has very good application prospect. (by machine translation)

Kinetics of the hydrogenation of 2-chloro-4-nitroaniline over skeletal nickel and supported palladium catalysts in an aqueous solution of 2-propanol

The kinetics of the liquid-phase hydrogenation of 2-chloro-4-nitroaniline in an aqueous solution of 2-propanol over skeletal nickel and supported palladium catalysts is studied. The selectivity of the reaction with respect to 2-chloro-1,4-phenylenediamine is determined. It is found that samples of supported palladium catalysts differ with respect to the amount of the active component and the nature of the support. Some of their structural characteristics are provided.

Zwitterionic Surfactant stabilized palladium nanoparticles as catalysts in aromatic nitro compound reductions

Palladium nanoparticles (NPs) stabilized by ImS3-14, a zwitterionic surfactant structurally related to ionic liquids, are revealed here to be good catalysts for the reduction of a large number of substituted aromatic nitro compounds. Our mass spectrometry results are consistent with the formation of amino products in a direct route, where the aromatic nitro compounds are initially reduced to nitroso compounds, which are then reduced to the hydroxylamine derivatives and finally to the anilines. Activation parameters showed that for most Pd catalysts reported in the literature, the mechanism seems to be similar, with lower enthalpy of activation (ΔH?) being compensated by more negative entropy of activation (ΔS?). As a result, the reaction is thermally compensated and the rate constants for most reactions rather similar. Furthermore, Pd NPs stabilized by ImS3-14 showed efficient catalytic activities for the reduction of aromatic nitro compounds, with high conversion and good selectivity even using very low loadings of metal.