581-43-1

Basic information

• Product Name: 2,6-Naphthalenediol
• Synonyms: 2,6-NAPHTHALENEDIOL;2,6-DIHYDROXYNAPHTHALENE;naphthalene-2,6-diol;TIMTEC-BB SBB000129;2,6-Naphthalenediol(2,6-Oh);2,6-DihydroxylNaphthalene;2,6-Dihydroxynaphthalin;2.6-DIHYDROXYNAPHTHALENE98%
• CAS NO: 581-43-1
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 209-465-6
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatics
• Mol File: 581-43-1.mol

Chemical Properties

• Melting Point: 223-225 °C(lit.)
• Boiling Point: 246.06°C (rough estimate)
• Flash Point: 193.5 °C
• Appearance: grey to brown powder
• Density: 1.0924 (rough estimate)
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Refractive Index: 1.5418 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.55±0.40(Predicted)
• Water Solubility: Soluble in methanol and hot water. Slightly soluble in water.
• BRN: 1238082
• CAS DataBase Reference: 2,6-Naphthalenediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Naphthalenediol(581-43-1)
• EPA Substance Registry System: 2,6-Naphthalenediol(581-43-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 581-43-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,6-Naphthalenediol is used as a key intermediate in the synthesis of various organic compounds, including 1,5-dichloro-2,6-diethynylnaphthalenes. It serves as a building block for the creation of complex molecules with specific properties and applications.
Used in Pharmaceutical Research:
In the field of pharmaceuticals, 2,6-Naphthalenediol is used to produce convulsions in mice for research purposes. This helps scientists study the effects of various drugs and compounds on the central nervous system and develop potential treatments for neurological disorders.
Used in Cell Biology:
2,6-Naphthalenediol exhibits antiproliferative activity towards certain cells, making it a valuable tool in cell biology research. It can be used to study the mechanisms of cell growth and proliferation, as well as to develop potential anti-cancer agents.
Used in Material Science:
In the field of material science, 2,6-Naphthalenediol is employed in the preparation of the first-generation rotaxane dendrimer. This unique molecular structure has potential applications in nanotechnology, molecular machines, and drug delivery systems.
Used in Dye and Pigment Industry:
2,6-Naphthalenediol is used in the production of several dyes and pigments, thanks to its ability to form stable and vibrant color compounds. These dyes and pigments find applications in various industries, including textiles, plastics, and printing.
Used in Tanning Industry:
In the tanning industry, 2,6-Naphthalenediol is used as a tanning agent. It helps to stabilize and preserve the collagen fibers in animal hides, resulting in a more durable and flexible leather product.
Used in Antioxidant and Antiseptic Formulations:
Due to its chemical properties, 2,6-Naphthalenediol is used in the formulation of antioxidants and antiseptics. It helps to prevent the oxidation of materials, prolonging their shelf life and maintaining their quality.
Used in Derivatives Production:
2,6-Naphthalenediol can be converted into various derivatives, such as amines, esters, ethers, and carboxylic derivatives. These derivatives have a wide range of applications in different industries, including pharmaceuticals, agrochemicals, and specialty chemicals.

InChI:InChI=1/C10H8O2/c11-9-3-1-7-5-10(12)4-2-8(7)6-9/h1-6,11-12H

Upstream product

• 613-20-7 2,6-naphthoquinone 
• 604-35-3 Cholesteryl acetate 
• 93-01-6 2-naphthol-6-sulfonic acid 
• 5486-55-5 2,6-dimethoxylnaphthalene 
• 135-19-3 β-naphthol 
• 135-76-2 sodium 2-naphthol-6-sulfonate 
• 22426-47-7 2,6-diacetoxynaphthalene 
• 581-75-9 naphthalene-2,6-disulfonic acid 
• 7647-01-0 hydrogenchloride 
• 52672-21-6 3,7-dihydroxy-naphthalene-1-sulfonic acid 
• 24157-81-1 2,6-diisopropylnaphthalene 
• 96783-79-8 2,6-bis(1-hydroperoxy-1-methylethyl)naphthalene 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 5486-55-5 2,6-dimethoxylnaphthalene 
• 98946-55-5 E-2-carboxy-5-hydroxycinnamic acid 
• 20258-98-4 2,6-dihydroxy-1-naphthaldehyde 
• 115440-09-0 1-phenylazo-2,6-dihydroxynaphthalene 
• 613-20-7 2,6-naphthoquinone 
• 607-20-5 hydroxy-6 naphthoquinone-1,2 
• 2243-67-6 naphthalene-2,6-diamine 
• 132178-78-0 1,5-dibromo-2,6-dihydroxynaphthalene 
• 856206-84-3 1,5-dibenzyl-naphthalene-2,6-diol 
• 173368-58-6 6-Benzoyloxy-[2]naphthol 
• 107619-48-7 2,6-diethoxynaphthalene 
• 6410-02-2 N,N'-Diphenyl-2,6-naphthylenediamine 
• 64523-89-3 2,6-Bis-diphenoxymethoxy-naphthalene 
• 58671-20-8 3,9-diphenyl-2,3,4,8,9,10-hexahydronaphtho[1,2-e:5,6-e']bis([1,3]oxazine) 

Relevant articles and documents

Method for preparing 2, 6-dihydroxy naphthalene by solid super base catalysis

The invention relates to a method for preparing 2, 6-dihydroxy naphthalene by solid super base catalysis. A solid super base is adopted as a catalyst and has the alkaline strength of more than 40, sulfonic acid groups can be activated by adding zinc oxide and Zn to enable the sulfonic acid groups to be more easily replaced by OH-, a low-energy quick path is realized, the conversion rate and the yield are improved, a grinding vacuum reactor is used as a reactor, the alkali metal hydroxide and the 2, 6-naphthalene disulfonate can be in full contact reaction in a solid phase state, the alkali metal hydroxide does not need to be heated to a molten state, the reaction temperature is greatly reduced, and the generation of byproducts such as tar is greatly reduced.

Preparation method of 2, 6-dihydroxy naphthalene

The invention relates to a preparation method of 2, 6-dihydroxy naphthalene. A grinding vacuum reactor is adopted as a reactor so that mixed alkali and 2, 6-naphthalene disulfonate can be fully contacted and reacted in a solid phase state, the mixed alkali does not need to be heated to a molten state, and the mixed alkali compounded by alkali metal hydroxide and magnesium oxide is adopted, the addition of magnesium oxide can activate sulfo groups, the sulfo groups can be replaced by OH- more easily, a low-energy rapid path is realized, the reaction temperature is greatly reduced, the generation of byproducts such as tar is greatly reduced, and the conversion rate and the yield are improved.

Preparation process for synthesizing 2,6-dihydroxynaphthalene

The invention discloses a preparation process for synthesizing 2,6-dihydroxynaphthalene. The preparation process comprises specific steps as follows: (1) in an autoclave, adding 33-34 parts of 2,6-naphthalenedisulfonic acid disodium salt, 12-18 parts of sodium hydroxide and 50-52 parts of water, performing stirring and heating to 280-320 DEG C, and performing stirring for reaction at the temperature for 8-10 hours; (2) stirring the solution obtained after the reaction in the step (1) and cooling the solution to the room temperature, adding sulfuric acid with concentration of 40%-60%, and performing neutralization reaction until PH being 0.5-2; (3) filtering a suspension from the step (2), transferring filtered solids to a container, adding 150-152 parts of hexane, 0.1-0.15 parts of a copper salt catalyst and 1-1.5 parts of a phase transfer catalyst, performing stirring and heating to 30-60 DEG C, adding 12-50 parts of an oxidant with concentration of 20%-30%, and continuing reaction at30-70 DEG C for 2-4 hours to obtain a 2,6-dihydroxynaphthalene solution. The preparation process has the advantages that salt-containing wastewater is reduced, dosage of sodium hydroxide and potassium hydroxide is reduced, and the yield is significantly increased.

The selective oxidation of substituted aromatic hydrocarbons and the observation of uncoupling via redox cycling during naphthalene oxidation by the CYP101B1 system

The cytochrome P450 monooxygenase enzyme CYP101B1, from Novosphingobium aromaticivorans DSM12444, efficiently and selectively oxidised a range of naphthalene and biphenyl derivatives. Methyl substituted naphthalenes were better substrates than ethylnaphthalenes and naphthalene itself. The highest product formation activity for a singly substituted alkylnaphthalene was obtained with 2-methylnaphthalene. The oxidation of alkylnaphthalenes was regioselective for the benzylic methyl or methine C-H bonds. The products from 1- and 2-ethylnaphthalene oxidation were highly enantioselective with a single stereoisomer being generated in significant excess. The disubstituted substrate, 2,7-dimethylnaphthalene, had a higher product formation activity than either 1- and 2-methylnaphthalene. Methyl substituted biphenyls were also better substrates than biphenyl and had similar biocatalytic parameters to 1-methylnaphthalene. CYP101B1 catalysed oxidation of 2- and 3-methylbiphenyl was selective for attack at the methyl C-H bonds. The exception was the turnover of 4-methylbiphenyl which generated 4′-(4-methylphenyl)phenol as the major product (70%) with 4-biphenylmethanol making up the remainder. The drug molecule diclofenac was also regioselectively oxidised to 4′-hydroxydiclofenac by CYP101B1. The activity of the CYP101B1 system with naphthalene was more complex and the rate of NADH oxidation increased over time but very little product, 1-naphthol, was generated. Addition of samples of 1-naphthol and 2-naphthol and low concentrations of 1,4-naphthoquinone induced rapid NADH oxidation activity in the in vitro turnovers in both the presence and absence of the cytochrome P450 enzyme. Hydrogen peroxide was generated in these reactions in absence of the P450 enzymes demonstrating that the ferredoxin and ferredoxin reductase in combination with quinones from naphthol oxidation and oxygen can undergo redox cycling giving rise to a form of uncoupling of the reducing equivalents.

A 2,6-dihydroxynaphthalene synthetic method

The invention discloses a synthetic method of 2,6 dihydroxy naphthalene, which comprises the following steps: placing 2,6 dihydroxy naphthalene in an alkali fusion pan, then a mixture of solid sodium hydroxide and nitrate is placed, Slowly heating to 150-170 DEG C, stirring, continuously heating to 320 DEG C, insulating for fusing alkali for 2.5-3.5 hours at 310-330 DEG C, then cooling to 200 DEG C, slowly dropping 450g of water for diluting, using a tri(octyl-decyl)amine solution for extracting 2,6-dihydroxy naphthalene, then acidifying the extracted 2, 6-dihydroxy naphthalene by sulfuric acid, and filtering and refining filter cake by an ethanol water mixed solvent to obtain 2,6-dihydroxy naphthalene. According to the synthetic method of 2,6-dihydroxy naphthalene, the used inorganic solvent is a mixture of potassium nitrate, sodium nitrite and sodium nitrate. According to the invention, viscosity of an alkali fusion material is low, fluidity is good, material can be uniformly mixed, and alkali fusion effect is good. In addition, under high temperature condition for alkali fusion, no decomposition problem of oxidation organic matter is generated, and no difficult separating problem is generated for the mixture.

A convenient and efficient synthesis of 2,6-dihydroxynaphthalene

A convenient synthesis of 2,6-dihydroxynaphthalene from 6-bromo-2-naphthol has been achieved with high overall yield (52%) and good purity (95.7%) based on the conversion of 6-(methoxymethoxy)-2-naphthaldehyde to 6- (methoxymethoxy)-2-naphthol formate by a Baeyer-Villiger oxidation- rearrangement. Compared with the reported methods, the reaction conditions are milder and the work-up of each step is much simpler. Moreover, 6-bromo-2-naphthol as the starting material for the synthesis is readily available.

Demethylation of aromatic methyl ethers using ionic liquids under microwave irradiation

An efficient demethylation reaction for aromatic methyl ethers has been developed. Deprotection reactions give high yields with butylpyridinium bromide under microwave irradiation. Basic and acidic functional groups are tolerated if the reaction is performed under acidic conditions.

Photoarylation/alkylation of bromonaphthols

The photochemistry of 6-bromo-2-naphthols has been studied in acetonitrile, aqueous acetonitrile, and isopropyl alcohol in the absence and in the presence of triethylamine by product distribution analysis, laser flash photolysis (LFP), fluorescence, phosp

Solvent and temperature effects in the free radical aerobic oxidation of alkyl and acyl aromatics catalysed by transition metal salts and N-hydroxyphthalimide: New processes for the synthesis of p-hydroxybenzoic acid, diphenols, and dienes for liquid crystals and cross-linked polymers

The aerobic oxidation of 4,4′-diisopropyldiphenyl and 2,6-diisopropylnaphthalene, catalysed by N-hydroxyphthalimide and Co(II) salts, leads to the corresponding tertiary benzyl alcohols with high conversion and selectivity under mild conditions (temperature 30-60°C and atmospheric pressure). Solvent and temperature effects, as resulting from the pioneering work of C. Walling, and more recently from the conclusive resolution of K. U. Ingold and co-workers on a quantitative kinetic basis, strongly affect the selectivity of the aerobic oxidation. This is related to the ratio between the rate of β-scission of the alkoxyl radical, which leads to acetophenone derivatives, and the rate of hydrogen atom abstraction, leading to tertiary benzyl alcohols. These latter are efficiently converted either to diphenols for the production of liquid crystals, by reaction with H2O2, or to dienes, useful as cross-linking agents, by dehydration. The aerobic oxidation of p-hydroxyacetophenone catalysed by Mn(NO3)2 and Co(NO3)2 leads with high selectivity to p-hydroxybenzoic acid, a useful monomer for liquid crystals.

Synthesis of naphthalenediols by aerobic oxidation of diisopropylnaphthalenes catalyzed by N-hydroxyphthalimide (NHPI)/α, α′-azobisisobutyronitrile (AIBN)

Naphthalenediols were successfully synthesized in a one-pot reaction through the oxidation of diisopropylnaphthalenes with air catalyzed by N-hydroxyphthalimide (NHPI) combined with α,α′- azobisisobutyronitrile (AIBN) followed by decomposition with sulfuric acid. Thus, the oxidation of 2,6-diisopropylnaphthalene with air (20 atm) in the presence of AIBN (3 mol %) and NHPI (10 mol %) in CH3CN at 75°C for 21 h followed by treatment with 0.3 M H2SO4 gave 2,6-naphthalenediol in 92% yield.