1,6-Dihydroxynaphthalene

Base Information

• Chemical Name: 1,6-Dihydroxynaphthalene
• CAS No.: 575-44-0
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 29072990
• European Community (EC) Number: 209-386-7
• NSC Number: 7201
• UNII: 34C30KW024
• DSSTox Substance ID: DTXSID7052238
• Nikkaji Number: J70.175K
• Wikidata: Q27096881
• Metabolomics Workbench ID: 52303
• ChEMBL ID: CHEMBL204394
• Mol file: 575-44-0.mol

Synonyms:naphthalene-1,6-diol

Chemical Property of 1,6-Dihydroxynaphthalene

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Melting Point: 130-133 °C(lit.)
• Refractive Index: 1.725
• Boiling Point: 375.352 °C at 760 mmHg
• PKA: 9.26±0.40(Predicted)
• Flash Point: 193.545 °C
• PSA: 40.46000
• Density: 1.33 g/cm³
• LogP: 2.25100
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: very faint turbidity in Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 158

Purity/Quality:

98% ^*data from raw suppliers

1,6-Dihydroxynaphthalene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2)O)C(=C1)O

Technology Process of 1,6-Dihydroxynaphthalene

There total 20 articles about 1,6-Dihydroxynaphthalene 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: 54.0%

1,6-diacetoxynaphthalene (59335-81-8) → 1,6-dihydroxynaphthalene (575-44-0) + 1-acetoxy-6-hydroxynaphthalene + 6-acetoxy-1-hydroxynaphthalene

Guidance literature:

With lipase of Pseudomonas sp; water; In various solvent(s); at 25 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)01000-5

Reference yield: 29.0%

β-naphthol (135-19-3) → 2.6-dihydroxynaphthalene (581-43-1) + 1,7-Dihydroxynaphthalene (575-38-2) + 1,6-dihydroxynaphthalene (575-44-0) + 2,7-Dihydroxynaphthalene (582-17-2)

Guidance literature:

With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride; at -40 ℃; for 0.25h; Mechanism; Product distribution;

DOI:10.1016/S0040-4039(00)88105-8

Reference yield:

5-aminonaphthalene-2-sulfonic acid (119-79-9) + furan-2,3,5(4H)-trione pyridine (1:1) → 1,6-dihydroxynaphthalene (575-44-0) + 5-amino-2-naphthol (86-97-5) + 1-amino-naphthalene (134-32-7)

Guidance literature:

at 260 ℃; im Autoklaven;

upstream raw materials:

5-aminonaphthalene-2-sulfonic acid

2-amino-5-hydroxy-naphthalene-1-sulfonic acid

5-amino-2-naphthol

2-amino-1,5-naphthalenedisulfonic acid

Downstream raw materials:

naphthofluorescein

6-methoxy-1-naphthol

5-methoxynaphthalen-2-ol

6-hydroxy-[1,4]naphthoquinone

Refernces

• 1、 Olah, George A.,Keumi, Takashi,Lecoq, Jean Claud,Fung, Alexander P.,Olah, Judith A.. "Oxyfunctionalization of Hydrocarbons. 17. Acid-Dependent High Regioselectivity Hydroxylation of Naphthalene with Hydrogen Peroxide Giving 1- or 2-Naphthol". . p. 6148 - 6151. Retrieved 2007/10/02.
• 2、 -. "Bischoloroformate preparation method with phosgene removal and monochloroformate conversion". . . Retrieved 2008/06/13.