4,6-Diaminoresorcinol

Base Information

• Chemical Name: 4,6-Diaminoresorcinol
• CAS No.: 15791-87-4
• Molecular Formula: C6H8N2O2
• Molecular Weight: 140.142
• Hs Code.: 2922299090
• European Community (EC) Number: 928-257-2
• DSSTox Substance ID: DTXSID301021901
• Nikkaji Number: J81.883F
• Mol file: 15791-87-4.mol

Synonyms:Resorcinol,4,6-diamino- (7CI,8CI);1,3-Diamino-4,6-dihydroxybenzene;1,3-Dihydroxy-4,6-diaminobenzene;2,4-Diaminobenzene-1,5-diol;4,6-Diamino-1,3-benzenediol;4,6-Diaminoresorcin;4,6-Diaminoresorcinol;

Chemical Property of 4,6-Diaminoresorcinol

Chemical Property:

• Vapor Pressure: 5.29E-08mmHg at 25°C
• Refractive Index: 1.79
• Boiling Point: 430.1 °C at 760 mmHg
• PKA: 9.52±0.23(Predicted)
• Flash Point: 213.9 °C
• PSA: 92.50000
• Density: 1.542g/cm³
• LogP: 1.42460
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 140.058577502
• Heavy Atom Count: 10
• Complexity: 108

Purity/Quality:

98% ^*data from raw suppliers

4,6-DIAMINORESORCINOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1N)O)O)N
• General Description: 4,6-Diaminoresorcinol (DAR) is a key diaminobenzene diol used as a precursor in the synthesis of 2,6-disubstituted benzobisoxazoles, which are valuable building blocks for organic semiconductors. It reacts efficiently with orthoesters under optimized catalytic conditions, including rare earth metal triflates and pyridine, to form benzobisoxazole structures, enabling further derivatization into conjugated polymers for semiconductor applications.

Technology Process of 4,6-Diaminoresorcinol

There total 11 articles about 4,6-Diaminoresorcinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

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

Guidance literature:

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

DOI:10.1007/s11164-018-3477-y

Reference yield: 82.0%

→ 4,6-diamino-1,3-benzenediol (15791-87-4)

Guidance literature:

Reference yield: 80.0%

4,6-bis-phenylazo-resorcinol (15236-63-2) → 4,6-diamino-1,3-benzenediol (15791-87-4)

Guidance literature:

With hydrogen;

upstream raw materials:

4,6-dinitroresorcinol

4,6-bis-phenylazo-resorcinol

hydrogenchloride

2-hydroxy-5-hydroxyamino-[1,4]benzoquinone-1-oxime

Downstream raw materials:

2-amino-5-hydroxy-[1,4]benzoquinone-4-imine

2,2-dimethyl-propionic acid 2,4-bis-(2,2-dimethyl-propionylamino)-5-(2,2-dimethyl-propionyloxy)-phenyl ester

C₅₀H₅₆N₂O₆

2,6-bis(3,4,5-tridodecyloxyphenyl)benzo[1,2-d;5,4-d']bisoxazole

Refernces

An efficient synthesis of 2,6-disubstituted benzobisoxazoles: New building blocks for organic semiconductors

10.1021/ol802011y

The study presents an efficient synthesis method for 2,6-disubstituted benzobisoxazoles, which are promising building blocks for organic semiconductors. The key chemicals involved are diaminobenzene diols, specifically 2,5-diaminohydroquinone (DAHQ) and 4,6-diaminoresorcinol (DAR), which react with various orthoesters to form the desired benzobisoxazoles. Orthoesters, such as triethyl orthoformate, triethyl orthoacetate, trimethylsilyl ethyl orthopropiolate, triethyl orthobromoacetate, and triethyl orthochloroacetate, serve as both reactants and solvents in the reactions. The study explores different catalysts, including traditional acids like H2SO4 and rare earth metal triflates like Y(OTf)3 and La(OTf)3, to optimize the reaction conditions. The optimized conditions involve using DMSO as a cosolvent, a catalytic amount of metal triflate, and pyridine to enhance yields and reduce reaction temperatures. The synthesized benzobisoxazoles can be further transformed into monomers for the synthesis of conjugated polymers, as demonstrated by the synthesis of a soluble PBO derivative through the Arbuzov reaction and subsequent polymerization.