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| | 1,4-Dihydroxynaphthalene Basic information |
| | 1,4-Dihydroxynaphthalene Chemical Properties |
| Melting point | 191-192 °C (dec.) | | Boiling point | 246.06°C (rough estimate) | | density | 1.0924 (rough estimate) | | refractive index | 1.5178 (estimate) | | storage temp. | Refrigerator | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | crystals | | pka | pK1:9.37;pK2:10.93 (26°C，μ=0.65) | | color | Grey | | Water Solubility | slightly soluble | | BRN | 1307689 | | InChI | 1S/C10H8O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6,11-12H | | InChIKey | PCILLCXFKWDRMK-UHFFFAOYSA-N | | SMILES | Oc1ccc(O)c2ccccc12 | | CAS DataBase Reference | 571-60-8(CAS DataBase Reference) | | NIST Chemistry Reference | 1,4-Naphthalenediol(571-60-8) | | EPA Substance Registry System | 1,4-Naphthalenediol (571-60-8) |
| | 1,4-Dihydroxynaphthalene Usage And Synthesis |
| Chemical Properties | brown to greyish powder. 1,4-Naphthalenediol [571-60-8], mp 195℃, is synthesized by reduction of 1,4- naphthoquinone with sodium dithionite, or by hydrolysis of 4-amino-1-naphthol with 20 % sulfuric acid. It undergoes oxidation to give 1,4-naphthoquinone; amination to give 4-amino-1-naphthol; and methylation (MeOH – HCl) to give 4-methoxy-1-naphthol. | | 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. | | Definition | ChEBI: Naphthalene-1,4-diol is a naphthalenediol and a naphthohydroquinone. | | Biological Activity | 1,4-Dihydroxynaphthalene is a potent HSV-1 protease inhibitor with inhibitory effects on the HCMV protease, which can be used to study herpesviruses. | | References | [1] LAURIE S. TSURUDA A. D J Michael W Lamé. Formation of epoxide and quinone protein adducts in B6C3F1 mice treated with naphthalene, sulfate conjugate of 1,4-dihydroxynaphthalene and 1,4-naphthoquinone[J]. Archives of Toxicology, 1995, 69 6: 362-367. DOI:10.1007/s002040050185. |
| | 1,4-Dihydroxynaphthalene Preparation Products And Raw materials |
| Raw materials | 5,6,11,12,17,18-Trinaphthylenehexone-->1,4-Naphthalenediol, 1-acetate-->trans-1-methoxy-1,3-butadiene-->Propanoic acid,3-[(1,4-dihydro-1,4-dioxo-2-naphthalenyl)thio]--->Dodecyl aldehyde-->1,4-DIACETOXYNAPHTHALENE-->2-AMINO-3-CHLORO-1,4-NAPHTHOQUINONE-->1,4-Benzoquinone-->Butyraldehyde-->Naphthalene-->1-Naphthol-->3,4-Dihydro-2H-pyran-->1-Tetralone | | Preparation Products | 2-Chloro-1,4-naphthoquinone-->4-METHOXY-1-NAPHTHOL-->2,3-Dihydro-1,4-naphthoquinone |
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