1,4-Dihydroxynaphthalene

Base Information

• Chemical Name: 1,4-Dihydroxynaphthalene
• CAS No.: 571-60-8
• Molecular Formula: C10H8 O2
• Molecular Weight: 162.188
• Hs Code.: 2907299090
• European Community (EC) Number: 209-336-4
• UNII: AML1P6T42C
• DSSTox Substance ID: DTXSID5060350
• Nikkaji Number: J6.537D
• Wikidata: Q27115786
• Metabolomics Workbench ID: 54917
• ChEMBL ID: CHEMBL206816
• Mol file: 571-60-8.mol

Synonyms:1,4-dihydroxynaphthalene;1,4-naphthohydroquinone

Chemical Property of 1,4-Dihydroxynaphthalene

Chemical Property:

• Appearance/Colour: almost white Solid
• Melting Point: 191-192 °C (dec.)
• Refractive Index: 1.5178 (estimate)
• Boiling Point: 391 °C at 760 mmHg
• PKA: pK1:9.37;pK2:10.93 (26°C，μ=0.65)
• Flash Point: 202.5 °C
• PSA: 40.46000
• Density: 1.33 g/cm³
• LogP: 2.25100
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dihydroxynaphthalene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,T
• Statements: 22-37/38-41-43-36/37/38-25
• Safety Statements: 26-39-45-36/37/39-28A-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=C2O)O
• Uses: 1,4-Dihydroxynaphthalene is frequently used in organic synthesis as a reagent. In particular, it is used in the synthesis of a pH independent and cell permeant fluorescent dye, a hydroxyl regioisomeric 3'',4''-benzorhodol, which can be used as a fluorescent chemosensor and biomarker for biological applications.

Technology Process of 1,4-Dihydroxynaphthalene

There total 86 articles about 1,4-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: 100.0%

[1,4]naphthoquinone (130-15-4) → 1,4-Dihydroxynaphthalene (571-60-8)

Guidance literature:

With acetic acid; zinc; Ambient temperature; sonication, less than 5 min;

DOI:10.1055/s-1991-26417

Reference yield: 93.0%

3-mercaptopropionic acid ethyl ester (5466-06-8) + [1,4]naphthoquinone (130-15-4) → 1,4-Dihydroxynaphthalene (571-60-8) + 2-[2-(ethoxycarbonyl)ethyl]thio-1,4-naphthoquinone (234112-67-5)

Guidance literature:

In ethanol; at 20 ℃;

DOI:10.1246/cl.1999.503

Reference yield: 89.0%

1,4-diacetoxynaphthalene (5697-00-7) → 1,4-Dihydroxynaphthalene (571-60-8) + 1-acetoxy-4-hydroxynaphthalene (70662-30-5)

Guidance literature:

With lipase of Pseudomonas sp; water; In various solvent(s); at 25 ℃; for 2.5h;

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

upstream raw materials:

1,4-dioxane

1,1-Bisethylene

[1,4]naphthoquinone

α-naphthol

Downstream raw materials:

4-methoxynaphth-1-ol

1,4-dimethoxynaphthalene

6,11-dihydroxy-5,12-naphthacenedione

2-trityl-[1,4]naphthoquinone

Refernces

• 1、 Rieck, John A.,Grunwell, John R.. "A New Synthesis of Anthraquinones". . p. 3512 - 3513. Retrieved 1980.
• 2、 Yagodkin, Elisey,McGarry, Kathryn A.,Douglas, Christopher J.. "Preparation of 6,11-dihydroxy-5,12-tetracenedione". . p. 360 - 363. Retrieved 2011.
• 3、 Yamakado, Takuya,Takahashi, Shota,Watanabe, Kazuya,Matsumoto, Yoshiyasu,Osuka, Atsuhiro,Saito, Shohei. "Conformational Planarization versus Singlet Fission: Distinct Excited-State Dynamics of Cyclooctatetraene-Fused Acene Dimers". . p. 5438 - 5443. Retrieved 2018.
• 4、 Gong, Qijie,Yang, Fulai,Hu, Jiabao,Li, Tian,Wang, Pengfei,Li, Xiang,Zhang, Xiaojin. "Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics". . . Retrieved 2021/07/25.
• 5、 Agarwal, Rishi G.,Mayer, James M.,Wise, Catherine F.. "Determining Proton-Coupled Standard Potentials and X-H Bond Dissociation Free Energies in Nonaqueous Solvents Using Open-Circuit Potential Measurements". supporting information. p. 10681 - 10691. Retrieved 2020/07/06.