15791-87-4

Usage

Uses

Used in Cosmetic Industry:
4,6-Diaminoresorcinol is used as a hair dye intermediate for its ability to create a range of vibrant, long-lasting hair colors. Its solubility in both alcohol and water makes it a versatile compound in the formulation of hair dye products.
Used in Hair Dye Formulation:
4,6-Diaminoresorcinol is used as a key component in hair dye formulations to achieve the desired color intensity and longevity. Its chemical properties allow it to interact with hair proteins, ensuring that the color is effectively deposited and maintained over time.

InChI:InChI=1/C6H8N2O2/c7-3-1-4(8)6(10)2-5(3)9/h1-2,9-10H,7-8H2

Synthetic route

1,3-dihydroxy-2-chloro-4,6-dinitrobenzene (116920-31-1) → 4,6-diamino-1,3-benzenediol (15791-87-4)

Conditions	Yield
With 15% palladium on carbon; ammonium acetate; hydrogen In isopropyl alcohol at 60℃; under 15001.5 Torr; for 0.0466667h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Autoclave;	88%
With trifluoroacetic acid; palladium In water

Upstream product

• 616-74-0 4,6-dinitroresorcinol 
• 15236-63-2 4,6-bis-phenylazo-resorcinol 
• 7647-01-0 hydrogenchloride 
• 98197-89-8 2-hydroxy-5-hydroxyamino-[1,4]benzoquinone-1-oxime 
• 119014-47-0 2-amino-5-hydroxy-[1,4]benzoquinone-4-imine 
• 116920-31-1 1,3-dihydroxy-2-chloro-4,6-dinitrobenzene 
• 7440-44-0 pyrographite 
• 15236-63-2 4,6-bis(phenylazo)resorcinol 
• 108-58-7 Resorcinol diacetate 

Downstream Products

• 119014-47-0 2-amino-5-hydroxy-[1,4]benzoquinone-4-imine 
• 649767-96-4 C₅₀H₅₆N₂O₆ 
• 1151760-18-7 2,6-bis(3,4,5-trihexadecyloxyphenyl)benzo[1,2-d;5,4-d']bisoxazole 
• 1151760-17-6 2,6-bis(3,4,5-tritetradecyloxyphenyl)benzo[1,2-d;5,4-d']bisoxazole 
• 1151760-16-5 2,6-bis(3,4,5-tridecyloxyphenyl)benzo[1,2-d;5,4-d']bisoxazole 
• 1151760-15-4 2,6-bis(3,4,5-tridodecyloxyphenyl)benzo[1,2-d;5,4-d']bisoxazole 
• 429693-76-5 2,2-dimethyl-propionic acid 2,4-bis-(2,2-dimethyl-propionylamino)-5-(2,2-dimethyl-propionyloxy)-phenyl ester 

Relevant academic research and scientific papers

Hydrogenation–dechlorination of 2-chloro-4,6-dinitroresorcinol over Pd/C catalysts

Pd catalysts supported on active carbon (Pd/C) prepared by impregnation–deposition were used in catalytic hydrogenation and hydrodechlorination (HDC) of 2-chloro-4,6-dinitroresorcinol (CDNR). Characterization by X-ray diffraction, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy, and transmission electron microscopy revealed Pd species in the form of ~3.0-nm Pd nanoparticles composed of Pd0 and Pdn+ dispersed highly on active carbon. Pd/C catalysts with high Pd0/(Pd0?+?Pdn+) exhibited high active for hydrogenation of CDNR, while the yield of the target product 4,6-diaminoresorcinol (DAR) largely depended on the solvent media. The correlations of the dielectric constants of the solvents with the activity and selectivity were obtained. Alkanol or acetic acid aqueous solutions were favorable for HDC. No 2-chloro-4,6-diaminoresorcinol product was detected when the reaction was carried out using 80?% ethanol/water media. XPS, energy-dispersive spectroscopy, and high-resolution transmission electron microscopy revealed that strong Cl adsorption caused the decrease in activity and selectivity for DAR of the Pd/C catalysts.

Preparation method of 4,6 - diphenyl azo resorcinol and 4,6 - diaminoresorcinol (by machine translation)

The invention relates to a preparation method of 4,6 - diphenyl azo resorcinol and 4,6 - diaminoresorcinol, wherein the phenylamine diazonium liquid is obtained by diazo reaction of aniline as a raw material; and the aniline diazonium liquid, the liquid base and the resorcinol aqueous solution are pumped into the dynamic tubular reactor according to a certain proportion, a flow speed and a sequential pump to obtain 4,6 -diphenyl azo resorcinol; and a high-purity 4,6 - diaminoresorcinol is obtained through hydrogenation. 4,6 -diphenyl azo resorcinol prepared by the present aniline method contains a small amount 2, 4 of substituted isomers and three-substituted impurities, and the problem of subsequent hindrance polymerization is influenced by virtue of the method, the purity of the diphenyl azo resorcinol obtained by the method is high, and the obtained 4,6 - 4,6 -diaminoresorcinol is less in impurities. (by machine translation)

Production method of 4,6-diaminoresorcin

The present invention relates to a novel production method of 4,6-diaminoresorcin, and to 2-sulfonic acid-4,6-dinitroresorcin as its intermediate and salts thereof. The target compound is obtained by (R1) sulfonating resorcin (A) to obtain resorcin 2,4,6-trisulfonate (B), (R2) nitrating the compound (B) to obtain 2-sulfonic acid-4,6-dinitroresorcin (C), (R3) hydrolyzing the compound (C) to obtain 4,6-dinitroresorcin (D), and finally (R4) reducing the compound (D) to obtain 4,6-diaminoresorcin (E):

Process for preparation of 4,6-diaminoresorcinol or salts thereof

The invention relates to a process for preparation of 4,6-diaminoresorcinol or salts thereof by reducing 4,6-bis(substituted)phenylazoresorcinol expressed by the formula [1]wherein, R denotes a halogen atom, an alkyl group having 1-5 carbon atoms, a hydroxycarbonyl group or an alkoxy group having 1-5 carbon atoms, n denotes 0 or any integer of 1-5, and two or more groups R may be same or different each other,for example, 4,6-bisphenylazoresorcinol, with hydrogen in the presence of a metal catalyst to obtain 4,6-diaminoresorcinol or salts thereof, characterized in that an aliphatic nitrile compound (for example, acetonitrile) is used as a solvent, or characterized in that the reduction is carried out by using at least one organic solvent selected from aliphatic nitrile compounds, aliphatic alcohols having 3-5 carbon atoms, dioxane and ethylene glycol monomethyl ether, etc. as a solvent and furthermore in the presence of a filter aid (for example, active carbon). According to the said preparation process, 4,6-diaminoresorcinol with high purity can be easily obtained from 4,6-bis(substituted)phenylazoresorcinol in a high yield.

Process for the preparation of 4,6-diaminoresorcinol

4,6-diaminoresorcinol can be prepared in a plurality of steps in such a way that a) 1,3-dichlorobenzene is nitrated with a mixed acid of HNO3, H2 SO4 and SO3 at 0 to 40° C. in anhydrous H2 SO4, b) the resulting 1,3-dichloro-4,6/2,4-dinitrobenzene isomeric mixture is first reacted with benzyl alcohol in the presence of a strong base at -15° C. to +15° C. and then at 20° to 40° C. to give the dibenzyloxy compound and c) the 1,3-dibenzyloxy-4,6-dinitrobenzene isomer arising in pure form in b) is converted to the 4,6-diaminoresorcinol by catalytic hydrogenation.

High performance heterocycle oligomers and blends

Linear or multidimensional, crosslinking, solvent resistant oxazole, thiazole, or imidazole (i.e., heterocycle) oligomers and blends of the crosslinking oligomers and noncrosslinking comparable polymers are described. The oligomers are prepared by reacting tetraamines, diaminodiols, or diaminothiols (i.e. four--functional compounds) with poly-carboxylic acid halides, and crosslinking phenylimide end cap monomers in a suitable solvent under an inert atmosphere.

Aqueous reduction process for halo-nitro-phenols

An aminophenolic compound can be synthesized by contacting a halo-nitro-phenolic compound, such as 2-chloro-4,6-dinitrorescorcinol, with a hydrogenating agent, such as hydrogen, and a catalyst, such as palladium-on-carbon, in an aqueous solution in the presence of an acid such as phosphoric acid.