15791-87-4

Basic information

• Product Name: 4,6-Diaminoresorcinol
• Synonyms: 4,6-DIAMINORESORCINOL;4,6-Diaminoresorcinol dihydrochlorid;4,6-DIAMINORESORCINOL 2HCL;DIAMINO RESORCINOL;4,6-Diamino-1,3-benzenediol;4,6-Diaminoresorcino;1,3-Benzenediol, 4,6-diaMino-;4,6-diaMinobenzene-1,3-diol
• CAS NO: 15791-87-4
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.14
• Mol File: 15791-87-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 430.1 °C at 760 mmHg
• Flash Point: 213.9 °C
• Appearance: /
• Density: 1.542
• Vapor Pressure: 5.29E-08mmHg at 25°C
• Refractive Index: 1.79
• PKA: 9.52±0.23(Predicted)
• CAS DataBase Reference: 4,6-Diaminoresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Diaminoresorcinol(15791-87-4)
• EPA Substance Registry System: 4,6-Diaminoresorcinol(15791-87-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 15791-87-4(Hazardous Substances Data)

Usage

General Description

4,6-Diaminoresorcinol, also known as DAR, is a type of aromatic amine compound primarily used in the field of cosmetics, particularly as a hair dye. It is one of the primary intermediates used in the creation of a range of vibrant, long-lasting hair colors. It is usually supplied in a stable solid form and is soluble in both alcohol and water. When used properly, it is considered to be relatively safe, but may still pose potential risks like skin irritation or allergic reactions. It's crucial to use it while following appropriate safety precautions.

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 
• 108-58-7 Resorcinol diacetate 
• 116920-31-1 1,3-dihydroxy-2-chloro-4,6-dinitrobenzene 
• 7440-44-0 pyrographite 
• 15236-63-2 4,6-bis(phenylazo)resorcinol 

Downstream Products

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

Relevant articles and documents

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.

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 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.