Naphthalene-1,8-diol

Base Information

• Chemical Name: Naphthalene-1,8-diol
• CAS No.: 569-42-6
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 2907299090
• European Community (EC) Number: 209-316-5
• UNII: JEW2VB8R33
• DSSTox Substance ID: DTXSID80205435
• Nikkaji Number: J135.089G
• Wikidata: Q72493458
• Metabolomics Workbench ID: 126313
• ChEMBL ID: CHEMBL203537
• Mol file: 569-42-6.mol

Synonyms:1,8-DHN;1,8-dihydroxynaphthalene

Chemical Property of Naphthalene-1,8-diol

Chemical Property:

• Vapor Pressure: 3.62E-06mmHg at 25°C
• Melting Point: 142-143℃
• Refractive Index: 1.725
• Boiling Point: 375.4 °C at 760 mmHg
• PKA: 6.36±0.10(Predicted)
• Flash Point: 193.5 °C
• PSA: 40.46000
• Density: 1.33g/cm³
• LogP: 2.25100
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

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

Naphthalene-1,8-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=CC=C2)O
• Uses: 1,8-Dihydroxynaphthalene (DHN) can be used as:An intermediate in the preparation of benzo analogs of spiromamakone A.A starting material to synthesize naphthopyran derivatives.An intermediate in the total synthesis of palmarumycin CP17 analogs.

Technology Process of Naphthalene-1,8-diol

There total 29 articles about Naphthalene-1,8-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: 86.0%

1,8-naphthosultone (83-31-8) → 1,8-dihydroxynaphthalene (569-42-6)

Guidance literature:

With potassium hydroxide; at 300 ℃; for 0.5h;

DOI:10.1039/a901076i

Reference yield: 67.0%

1,1-dimethyl-1H,3H-naphtho[1,8-cd][1,2,6]oxasilaborinin-3-ol → 1,8-dihydroxynaphthalene (569-42-6)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; methanol; dodecane; at 20 ℃;

DOI:10.1002/anie.201805086

Reference yield: 60.0%

1,8-naphthalenesultone → 1,8-dihydroxynaphthalene (569-42-6)

Guidance literature:

With potassium hydroxide; for 0.25h; Inert atmosphere;

DOI:10.1021/acs.organomet.6b00202

upstream raw materials:

8-hydroxy-naphthalene-1-sulfonic acid

4,5-dihydroxy-1-naphthalene-sulfonic acid

1,8-naphthosultam

8-anilino-1-naphthalenesulfonate

Downstream raw materials:

1-(1,8-dihydroxynaphthalen-2-yl)ethanone

8-methoxy-naphthalen-1-ol

1,8-naphthylenephenyl phosphite

2-(4-Bromo-phenoxy)-1,3-dioxa-2-phospha-phenalene

Refernces

• 1、 Su, Bo,Hartwig, John F.. "Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C?H Bonds in Fused Polycyclic Arenes and Heteroarenes". . p. 10163 - 10167. Retrieved 2018.
• 2、 Krempner, Clemens,Manankandayalage, Chamila P.,Unruh, Daniel K.. "Boronic, diboronic and boric acid esters of 1,8-naphthalenediol-synthesis, structure and formation of boronium salts". supporting information. p. 4834 - 4842. Retrieved 2020/04/27.