2-Chloro-p-phenylenediamine

ChEBI: A diamine that is 1,4-phenylenediamine substituted at position 2 by a chloro group.

2-chloro-1,4-phenylenediamine is a diamine that is 1,4-phenylenediamine substituted at position 2 by a chloro group. It has a role as a dye. It is a diamine and a member of monochlorobenzenes. It derives from a 1,4-phenylenediamine. It is a conjugate base of a 2-chloro-1,4-phenylenediaminium.

General procedure: In Example 1, the m-nitroacetophenone used was replaced with an equimolar 5-nitroindole, and at a hydrogen pressure of4.0 MPa for 24 hours at 80 C. The other procedure was the same as in to give 5-aminoindole in a yield of 98%, _: A solution of 16.44 mg (0.04 mmol) 4, 4'-dimethoxy-2, 2'-bipyridine silver 11.22 mg (0.1 mmol) of potassuim t-butoxide and 1 mL of 1, 4-dioxane were charged into an autoclave. After stirring, 165.15 mg (1 mmol) of m-nitroacetophenone was added and the mixture was stirred at 80 C. The reaction was carried out for 8 hours. After the reaction has finishedm the reaction solution was extracted with water and dichloromethane to collect the organic phase. Then, the organic phase was dried over anhydrous Na2SO4, suction filtered, rotary evaporated and chromatographed to give a yellow solid 3-acetanilide. Yield 96 %.The process of claim 3 wherein said compound of formula (II) is selected from the group consisting of p-phenylenediamine, 2-methyl-p-phenylenediamine, methoxy-para-phenylenediamine, chloro-para-phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2-methyl-5-methoxy-para-phenylenediamine, ...The process of claim 1 wherein said paraphenylenediamine of formula I is selected from the group consisting of ... 2-methoxy paraphenylenediamine, N-methyl-2-chloro paraphenylenediamine, N-furfuryl paraphenylenediamine, 3-methoxy-N'-methyl paraphenylenediamine, 2-chloro paraphenylenediamine, N-methyl paraphenylenediamine, 2, 3-dimethylparaphenylenediamine, 5-chloro-N'-methyl paraphenylenediamine, ...The one-step process of claim 3 wherein said paraphenylenediamine of formula (I) is selected from the group consisting of isopropyl-p-phenylenediamine, p-phenylenediamine, 2-methyl-p-phenylenediamine, methoxy-paraphenylenediamine, chloro-para-phenylenediamine, 2-methyl-5-methoxy-para-phenylenediamine, 2, 6-dimethyl-5-methoxy-para-phenylenediamine, N, N-dimethyl-para-phenylenediamine, 3-methyl-4-amino-N, N-diethylaniline, ...The following compounds with formula (IV) may in particular be cited: paraphenylenediamine, paratoluylenediamine, methoxyparaphenylenediamine, chloroparaphenylenediamine, 2, 3-dimethylparaphenylenediamine, 2, 6-dimethylparaphenylenediamine, 2, 6-diethylparaphenylenediamine, 2, 5-dimethylparaphenylenediamine, 2, 6-dimethyl 5-methoxyparaphenylenediamine, ...The method of claim 4 wherein said para-phenylenediamine is selected from the group consisting of p-phenylenediamine, 2-methyl-p-phenylenediamine, methoxy-para-phenylenediamine, chloro-para-phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2-methyl-5-methoxy-para-phenylenediamine, 2, 6-dimethyl-5-methoxy-para-phenyldiamine, ...(B) Representative oxidation bases of formula (II) exhibiting the greatest interest relative to the present invention are the following compounds: ... methoxy paraphenylenediamine dihydrochloride, paraphenylenediamine, 4-amino-N, N-di-beta-hydroxyethylaniline sulfate, N, N-dimethyl paraphenylenediamine dihydrochloride, chloroparaphenylenediamine, 3-methyl-4-amino-N-methylaniline dihydrochloride, 3-methoxy-4-amino-N-methylaniline dihydrochloride, 4-amino-N, beta-hydroxyethylaniline sulfate, ...methylamine, ... 1, 3-diamino-4-ethoxybenzene, 1, 4-diamino-2-methylbenzene, 1, 4-diamino-2-methoxybenzene, 1, 4-diamino-2-ethoxybenzene, 1, 4-diamino-2-chlorobenzene, 1, 4-diamino-2, 5-dimethylbenzene, 1, 4-diamino-2, 5-diethylbenzene, 1, 4-diamino-2-methyl-5-methoxybenzene, ...Specific examples of formula (A) compounds are: o-phenylenediamine m-phenylenediamine p-phenylenediamine , characterized in that the developer is selected from the group consisting of ... 1, 4-diamino-2, 6-dimethylbenzene; 1, 4-diamino-3, 5-diethylbenzene; 1, 4-diamino-2, 5-dimethylbenzene; 1, 4-diamino-2, 3-dimethylbenzene; 1), taking o-chloro-p-nitroaniline 86.3g (0.5mol), methanol 150ml and sodium methoxide 32.4g (0.6mol) in a 250ml reactor, the reactor is replaced by nitrogen after multiple times of air, sealed, heated to 150 C insulation 3h. 2) After the reaction of step 1) is completed, the temperature is lowered to room temperature, and the reaction liquid is distilled and recovered (collecting a fraction of 63 to 65 C) 145 ml of methanol to obtain crude General procedure: In a typical experiment, a mixture of nitroarene compound (1.0 mmol), ammonium formate (3.3 mmol, 208 mg, 1.1 equivalent), palladium catalyst (10 % Pdon activated carbon, 2 mol%, 21 mg) and silica (175 mg) was ball milled in thepresence of dry methanol (eta = 0.25 muL mg-1) for 90 minutes. After milling, a smallsample (? 1 mg) of the crude reaction mixture was suspended in methanol andimmediately analyzed by TLC (typically using dichloromethane : methanol = 20 : 1mixture as an eluent). The crude mixture was left in a well ventilated hood overnight, suspended in methanol and filtered over a Buechner funnel. Evaporation of the filtrateafforded the desired amino-derivative. If necessary, the final product was purified bycolumn chromatography.General procedure: A mixture of 3 mL of 0.015 mol L-1 aromatic nitro compound dissolved in tetrahydrofuran (THF), an aliquot of palladium nanoparticles, 300 muL of 2.0 mol L-1 NaCl solution and an aliquot of water were added into a reaction flask, totalizing 9 mL. Then, 900 muL of 0.5 mol L-1 NaBH4 solution freshly prepared was added to the above solution under continuous stirring. The final ratio H2O:THF was 2.3:1. The mixture was stirred at room temperature for 30 min. After this time, diethyl ether was added and the organic phase was separated and analyzed by gas chromatography (GC/MS) (chromatograph AgilentTechnologies model 7820A coupled to mass spectrometer Agilent Technologies model 5975, operating with acolumn HP5-ms).

This compound had some uses in hair dye formulations.

(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US

Molecular Weight:142.58
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:142.0297759
Monoisotopic Mass:142.0297759
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes