2,5-Diaminobenzene-1,4-diol

Base Information

• Chemical Name: 2,5-Diaminobenzene-1,4-diol
• CAS No.: 10325-89-0
• Molecular Formula: C6H8N2O2
• Molecular Weight: 140.142
• Hs Code.: 2922299090
• DSSTox Substance ID: DTXSID10352986
• Nikkaji Number: J81.487C
• Wikidata: Q82130432
• Mol file: 10325-89-0.mol

Synonyms:2,5-diaminobenzene-1,4-diol;10325-89-0;1,4-Benzenediol, 2,5-diamino-;2,5-Diamino-hydrochinon;SCHEMBL107865;DTXSID10352986;RLXBOUUYEFOFSW-UHFFFAOYSA-N;1,4-dihydroxy-2,5-diaminobenzene;AKOS006223434

Chemical Property of 2,5-Diaminobenzene-1,4-diol

Chemical Property:

• PSA: 92.50000
• 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: 106

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-DIAMINOHYDROQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1O)N)O)N

Technology Process of 2,5-Diaminobenzene-1,4-diol

There total 8 articles about 2,5-Diaminobenzene-1,4-diol 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: 97.2%

2,5-diaminocyclohexa-2,5-diene-1,4-dione (1521-06-8) → 2,5-diamino-1,4-benzenediol (10325-89-0)

Guidance literature:

With sodium thiosulfate; In water; at 40 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.molstruc.2019.07.041

Reference yield:

2,5-diamino-3,6-dichloro-1,4-benzoquinone (3908-48-3) → 2,5-diamino-1,4-benzenediol (10325-89-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 45 - 50 ℃; for 4h;

Reference yield:

chloranil (118-75-2) → 2,5-diamino-1,4-benzenediol (10325-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 27 percent aq. ammonium hydroxide / various solvent(s) / 1 h / 80 °C

2: H₂ / 10 percent Pd/C / H₂O / 4 h / 45 - 50 °C

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In water; 1: Substitution / 2: Hydrogenolysis;

upstream raw materials:

2,5-diamino-3,6-dichloro-1,4-benzoquinone

chloranil

sulfadimesine

benzene-1,2-diol

Downstream raw materials:

2-amino(t-butoxycarbonyl)-5-aminohydroquinone

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

benzo[1,2-d;4,5-d']bisoxazole

1,2-difluoro-4-oxo-4H-pyrido[3,2,1-kl]-8-(3'-hydroxy-4'-amino-(N-2-fluoro-4-nitrophenyl)-phenyl)-5-carboxylic acid

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.