575-38-2

Usage

Uses

Used in Organic Synthesis:
1,7-Dihydroxynaphthalene is used as a key intermediate for the synthesis of various organic compounds due to its unique chemical structure and reactivity.
Used in Pharmaceutical Industry:
1,7-Dihydroxynaphthalene is used as a building block for the development of pharmaceutical compounds, contributing to the creation of new drugs and therapies.
Used in Agrochemicals:
1,7-Dihydroxynaphthalene is utilized as a starting material in the production of agrochemicals, such as pesticides and fertilizers, to enhance crop protection and yield.
Used in Dye Industry:
1,7-Dihydroxynaphthalene is employed as a precursor in the synthesis of dyes, providing a foundation for the development of new colorants and pigments.
Used in Environmental Applications:
1,7-Dihydroxynaphthalene is used in the removal of dihydroxynaphthalenes from aqueous solutions through the action of an oxidoreductase enzyme, polyphenol oxidase, and biopolymer chitosan, aiding in environmental protection and pollution control.

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

Synthetic route

1,7-diacetoxynaphthalene (51850-49-8) → 1,7-Dihydroxynaphthalene (575-38-2) + 7-hydroxynaphthalen-1-yl acetate + 7-acetoxy-1-hydroxynaphthalene

Conditions	Yield
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 0.6h; Hydrolysis; deacetylation;	A n/a B n/a C 78%

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)

Conditions	Yield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -40℃; for 0.25h; Mechanism; Product distribution;	A 25.5% B 29% C 11% D 3.5%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -40℃; for 0.25h;	A 25.5% B 29% C 11% D 3.5%

α-naphthol (90-15-3) → 1,7-Dihydroxynaphthalene (575-38-2) + 1,5-dihydroxynaphthalene (83-56-7)

Conditions	Yield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -20℃; for 0.5h; Mechanism; Product distribution;	A 17.5% B 25.5%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -20℃; for 0.5h;	A 17.5% B 25.5%

6-methoxy-1,4-dihydro-1,4-epoxidonaphthalene (19061-33-7) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 130℃; for 7.5h;	23%

6-amino-4-hydroxy-2-naphthalenesulfonic acid (90-51-7) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sulfuric acid at 200℃;
With hydrogenchloride at 200℃;
With phosphoric acid at 200℃;
With formic acid at 200℃;

7-hydroxy-naphthalene-1-sulfonic acid (132-57-0) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With potassium hydroxide at 245 - 255℃; durch Verschmelzen;
With potassium hydroxide

8-amino-2-naphthalenesulfonic acid (119-28-8) + furan-2,3,5(4H)-trione pyridine (1:1) → 1,7-Dihydroxynaphthalene (575-38-2) + 8-amino-2-naphthol (118-46-7) + 8-hydroxy-naphthalene-2-sulfonic acid (20191-62-2)

Conditions	Yield
at 260℃; unter Druck;

2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sulfuric acid at 200℃;
With hydrogenchloride at 200℃;
With phosphoric acid at 200℃;
With formic acid at 200℃;

1,7-dihydroxy-2-naphthoic acid (86699-99-2) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With aniline

β-naphthol (135-19-3) → 2,6-Dihydroxynaphthalene (581-43-1) + 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With hydrogen fluoride; boron trifluoride; dihydrogen peroxide at -50℃; for 0.5h; Mechanism; Product distribution; other naphthol, other temp.;

4.6-dihydroxy-naphthalene-disulfonic acid-(2.7) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sulfuric acid at 200℃;
With hydrogenchloride at 200℃;
With phosphoric acid at 200℃;
With formic acid at 200℃;

4.6-dihydroxy-naphthalene-sulfonic acid-(2) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With sulfuric acid at 200℃;
With hydrogenchloride at 200℃;
With phosphoric acid at 200℃;
With formic acid at 200℃;

7-hydroxy-naphthalene-sulfonic acid-(1) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
With potassium hydroxide at 230℃;
With potassium hydroxide; sodium hydroxide at 230℃;

7-hydroxy-naphthalene-1-sulfonic acid (132-57-0) + potash → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
Verschmelzen;

sulfuric acid (7664-93-9) + 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid (90-40-4) → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
at 200℃;

1,7-dihydroxy-2-naphthoic acid (86699-99-2) + water (7732-18-5) → carbon dioxide (124-38-9) + 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
at 160℃;

1,7-dihydroxy-2-naphthoic acid (86699-99-2) + aniline (62-53-3) → carbon dioxide (124-38-9) + 1,7-Dihydroxynaphthalene (575-38-2)

1-bromo-4-methoxy-benzene (104-92-7) + sodium → 1,7-Dihydroxynaphthalene (575-38-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 22 percent / NaNH2, t-butyl alcohol / 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 55 °C 2: 23 percent / NaH, C2H5SH / dimethylformamide / 7.5 h / 130 °C View Scheme

1,7-Dihydroxynaphthalene (575-38-2) + magnesium methyl carbonate (4861-79-4) → 1,7-dihydroxy-2-naphthoic acid (86699-99-2)

Conditions	Yield
In N,N-dimethyl-formamide at 180℃; under 25857.4 Torr; for 6h;	100%

1,7-Dihydroxynaphthalene (575-38-2) + dimethyl sulfate (77-78-1) → 1,7-dimethoxynaphthalene (5309-18-2)

Conditions	Yield
With potassium hydroxide In water for 5h;	98%
With sodium hydroxide for 1h; Heating;	96%
With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water at 0℃;	95%

1,7-Dihydroxynaphthalene (575-38-2) + tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → naphthalene-1,7-diyl bis(2,3,4-tri-O-acetyl-β-D-xylopyranoside)

Conditions	Yield
With boron trifluoride diethyl etherate; triethylamine In dichloromethane at 20℃; for 2h;	96%

trifluoromethylsulfonic anhydride (358-23-6) + 1,7-Dihydroxynaphthalene (575-38-2) → naphthalene-1,7-diyl bis(trifluoromethanesulfonate) (152873-81-9)

Conditions	Yield
With pyridine	95%
With pyridine 1.) 0 deg C, 5 min, 2.) 0 deg C to r.t., 24 h; Yield given;

potassium thiocyanate + 1,7-Dihydroxynaphthalene (575-38-2) → 2,8-dihydroxy-thionaphthoic acid amide

Conditions	Yield
With hydrogen fluoride	95%

1,7-Dihydroxynaphthalene (575-38-2) → bispropargyl ether of 1,7-dihydroxynaphthalene (20009-42-1)

Conditions	Yield
	91%

3,5-bis((tetrahydro-2H-pyran-2-yl)oxy)benzoic acid (264276-67-7) + 1,7-Dihydroxynaphthalene (575-38-2) → C44H48O12

Conditions	Yield
Stage #1: 3,5-bis((tetrahydro-2H-pyran-2-yl)oxy)benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 1,7-Dihydroxynaphthalene In dichloromethane at 20℃; for 3h;	91%

1,7-Dihydroxynaphthalene (575-38-2) → 6-hydroxy-[1,4]naphthoquinone (4923-53-9)

Conditions	Yield
With methylene blue In methanol; water at 20℃; under 7500.75 Torr; for 0.266667h; Irradiation; Flow reactor;	87%
With oxone In water; acetonitrile at 20℃; for 10h;	15%
With methanol; potassium nitrososulfonate

1,7-Dihydroxynaphthalene (575-38-2) + benzene (71-43-2) → 7-hydroxy-4-phenyl-1-tetralone

Conditions	Yield
With aluminum tri-bromide at 25℃; for 48h;	87%

1,7-Dihydroxynaphthalene (575-38-2) + acetic anhydride (108-24-7) → 1,7-diacetoxynaphthalene (51850-49-8)

Conditions	Yield
With pyridine for 3h; Inert atmosphere;	86%
at 100℃;
With pyridine at 100℃;

1,7-Dihydroxynaphthalene (575-38-2) → 7-hydroxy-1-tetralone (22009-38-7)

Conditions	Yield
With aluminum tri-bromide; cyclohexane In various solvent(s) at 20℃; for 28h; Hydrogenation;	83%
With aluminum tri-bromide; cyclohexane In various solvent(s) at 25℃; for 24h;	80%

1,7-Dihydroxynaphthalene (575-38-2) + propionyl chloride (79-03-8) → 7-(propanoyloxy)naphthalen-1-yl propanoate

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 5h;	83%

1,7-Dihydroxynaphthalene (575-38-2) + methyl iodide (74-88-4) → 1,7-dimethoxynaphthalen-2(1H)-one (843652-67-5)

Conditions	Yield
With potassium carbonate In butanone Heating / reflux;	80%

1,7-Dihydroxynaphthalene (575-38-2) + 3-(2-bromoacetyl)-4-hydroxyfuran-2(5H)-one (1514896-23-1) → 3,3'-{2,2'-[naphthalene-1,7-diylbis(oxy)]bis(acetyl)}bis[4-hydroxyfuran-2(5H)-one] (1514896-33-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	79%

1,7-Dihydroxynaphthalene (575-38-2) + Chlorodiisopropylphosphane (40244-90-4) → C22H34O2P2

Conditions	Yield
With triethylamine In tetrahydrofuran at 85℃; for 1.5h; Inert atmosphere;	79%
With triethylamine In toluene at 35℃; for 10h; Inert atmosphere; Schlenk technique;

1,7-Dihydroxynaphthalene (575-38-2) + 1,6-dihydroxynaphthalene (575-44-0) + hexaethylphosphoric triamide (2283-11-6) → C28H32N2O4P2 (749885-09-4)

Conditions	Yield
Stage #1: 1,7-Dihydroxynaphthalene; hexaethylphosphoric triamide In acetonitrile at 20℃; for 0.333333h; Stage #2: 1,6-dihydroxynaphthalene In acetonitrile at 20℃; for 48h;	77%

diazodimedone (1807-68-7) + 1,7-Dihydroxynaphthalene (575-38-2) → 1-hydroxy-9,9-dimethyl-9,10-dihydrobenzo[kl]xanthen-11(8H)-one

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Schlenk technique;	76%

formaldehyd (50-00-0) + 1,7-Dihydroxynaphthalene (575-38-2) + malononitrile (109-77-3) → 2,10-diamino-4,12-dihydronaphtho<1,2-b:7,8-b'>dipyran-3,11-dicarbonitrile

Conditions	Yield
With piperidine In ethanol for 1h; Heating;	75%

2,6-Dihydroxynaphthalene (581-43-1) + 1,7-Dihydroxynaphthalene (575-38-2) + hexaethylphosphoric triamide (2283-11-6) → cyclo[(1,7-naphthylene)(2,6-naphthylene)-bis(diethyl phosphoramidite)] (749885-11-8)

Conditions	Yield
Stage #1: 1,7-Dihydroxynaphthalene; hexaethylphosphoric triamide In acetonitrile at 20℃; for 0.333333h; Stage #2: 2.6-dihydroxynaphthalene In acetonitrile at 20℃; for 48h;	75%

methanol (67-56-1) + 1,7-Dihydroxynaphthalene (575-38-2) → 1,7-dimethoxynaphthalene (5309-18-2) + 7-methoxynaphth-1-ol (67247-13-6)

Conditions	Yield
With hydrogenchloride for 168h; Ambient temperature;	A n/a B 74%

1,7-Dihydroxynaphthalene (575-38-2) + trifluoroacetic anhydride (407-25-0) → 1,7-bis(trifluoroacetoxy)naphthalene

Conditions	Yield
In diethyl ether for 48h; Ambient temperature;	73%

1,7-Dihydroxynaphthalene (575-38-2) + C35H20Cl2N4O4 (369384-87-2) → polymer; monomers: 2-(β-naphthylamino)-4,6-bis-(2-naphthoxy-3-carbonyl chloride)-S-triazine; 1,7-dihydroxynaphthalene

Conditions	Yield
With cetyltrimethylammonim bromide In N,N-dimethyl-formamide Heating;	73%

thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester (94582-84-0) + 1,7-Dihydroxynaphthalene (575-38-2) → 9-Diethylamino-3-hydroxy-11-methyl-benzo[a]phenothiazin-5-one

Conditions	Yield
Stage #1: thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester; 1,7-Dihydroxynaphthalene In dimethyl sulfoxide at 20℃; for 0.75h; Stage #2: With potassium dichromate In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #3: With hydrogenchloride In methanol; water; dimethyl sulfoxide at 20℃; for 1h;	73%

thiosulfuric acid S-(2-amino-5-diethylamino-3-methylphenyl) ester (94582-84-0) + 1,7-Dihydroxynaphthalene (575-38-2) → 9-diethylamino-3-hydroxy-11-methyl-benzo[a]phenoxazin-5-one

Conditions	Yield
With potassium dichromate In dimethyl sulfoxide for 0.333333h;	73%

1,7-Dihydroxynaphthalene (575-38-2) + 4-Carboxybenzaldehyde (619-66-9) → naphthalene-1,7-diyl bis(4-formylbenzoate) (1050414-41-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	72%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h;	51%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h;	51%

1,7-Dihydroxynaphthalene (575-38-2) + 2,7-Dihydroxynaphthalene (582-17-2) + hexaethylphosphoric triamide (2283-11-6) → cyclo[(1,7-naphthylene)(2,7-naphthylene)-bis(diethyl phosphoramidite)] (749885-12-9)

Conditions	Yield
Stage #1: 1,7-Dihydroxynaphthalene; hexaethylphosphoric triamide In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,7-Dihydroxynaphthalene In acetonitrile at 20℃; for 48h;	71%

1,7-Dihydroxynaphthalene (575-38-2) + 1,5-dihydroxynaphthalene (83-56-7) + hexaethylphosphoric triamide (2283-11-6) → cyclo[(1,7-naphthylene)(1,5-naphthylene)-bis(diethyl phosphoramidite)] (749885-10-7)

Conditions	Yield
Stage #1: 1,7-Dihydroxynaphthalene; hexaethylphosphoric triamide In acetonitrile at 20℃; for 0.333333h; Stage #2: 1,5-dihydroxynaphthalene In acetonitrile at 20℃; for 48h;	71%

1,7-Dihydroxynaphthalene (575-38-2) + 3-(ethyl(3-hydroxy-4-nitrosophenyl)amino)propane-1-sulfonic acid hydrochloride (915777-42-3) → C21H20N2O6S (1228763-87-8)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 4h; Inert atmosphere;	71%

di(tert-butyl)chlorophosphine (13716-10-4) + 1,7-Dihydroxynaphthalene (575-38-2) → 1,7-bis(ditertbutylphosphinyl)naphthalenediol

Conditions	Yield
With sodium hydride In tetrahydrofuran for 4h; Reflux; Inert atmosphere;	71%
With triethylamine In toluene at 35℃; for 10h; Inert atmosphere; Schlenk technique;

Upstream product

• 90-51-7 6-amino-4-hydroxy-2-naphthalenesulfonic acid 
• 132-57-0 7-hydroxy-naphthalene-1-sulfonic acid 
• 119-28-8 8-amino-2-naphthalenesulfonic acid 
• 90-40-4 2-amino-8-hydroxy-naphthalene-3,6-disulphonic acid 
• 86699-99-2 1,7-dihydroxy-2-naphthoic acid 
• 90-15-3 α-naphthol 
• 19061-33-7 6-methoxy-1,4-dihydro-1,4-epoxidonaphthalene 
• 135-19-3 β-naphthol 
• 51850-49-8 1,7-diacetoxynaphthalene 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 62-53-3 aniline 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 4923-53-9 6-hydroxy-[1,4]naphthoquinone 
• 51850-49-8 1,7-diacetoxynaphthalene 
• 5309-18-2 1,7-dimethoxynaphthalene 
• 64523-78-0 1,7-Bis-diphenoxymethoxy-naphthalene 
• 67247-13-6 7-methoxynaphth-1-ol 
• 93831-53-9 naphthalene-1,7-diyl bisphenylacetate 
• 93397-90-1 9-diethylamino-3-hydroxybenzophenoxazin-5-one 
• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 
• 31039-63-1 2,7-dihydroxy-[1,4]-naphthoquinone 
• 150712-58-6 1-acetoxy-7-methoxynaphthalene 
• 91344-50-2 8-methoxy-naphthalen-2-ol 
• 23682-05-5 1,7-Dianilino-naphthalin 
• 22009-38-7 7-hydroxy-1-tetralone 
• 235432-43-6 N-(para-tolyl)-7-hydroxy-1,4-naphthoquinone-4-imine 

Relevant academic research and scientific papers

HYDROXYLATION DES NAPHTOLS EN MILIEU SUPERACIDE

Hydroxylation of α and β naphtols by hydrogen peroxide in SbF5-HF occurs selectively on the non-phenolic ring, the electrophile reacting on the C-protonated substrate.

Regioselective hydrolysis of diacetoxynaphthalenes catalyzed by Pseudomonas sp. lipase in an organic solvent

Depending on the relative positions of the acetyl groups in the aromatic rings, the Pseudomonas sp. lipase-catalyzed hydrolysis of diacetoxynaphthalenes in tert-butylmethyl ether proceeds regioselectively to afford the corresponding monoacetates.

The Synthesis of 7-t-butylisobenzofuran-4,5-dione

The title compound has been prepared by a route in which the key step is the decarbonylation and subsequent Alder-Rickert cleavage of the adduct between 8-t-butyl-1,4-dihydro-1,4-epoxynaphthalene-5,6-dione and tetraphenylcyclopentadienone.

Oxyfunctionalization of Hydrocarbons. 17. Acid-Dependent High Regioselectivity Hydroxylation of Naphthalene with Hydrogen Peroxide Giving 1- or 2-Naphthol

The acid-catalyzed hydroxylation of naphthalene with 90percent hydrogen peroxide was investigated.Regioselectivity of the reaction depends on the acidity of the system and the solvent used.In anhydrous hydrogen fluoride or 70percent HF-30percent pyridine solution at -10 to +20 deg C 1-naphthol is the product formed in > 98percent selectivity.In contrast, 2-naphthol is obtained in hydroxylation in superacid (HF-BF3, HF-SbF5, HF-TaF5, FSO3H-SbF5) solution at -60 to -78 deg C in > 98percent selectivity.When 1-naphthol reacted under the latter conditions 1,5- and 1,7-dihydroxynaphthalene were obtained, while 2-naphthol gave 1,6-dihydroxynaphthalene (along with only minor amounts of 1,7-dihydroxynapthtalene).The mechanism of the reactions is discussed, contrasting electrophilic hydroxylation of naphthalene, giving predominantly 1-substitution, with reaction of protonated naphthalenes (i.e., naphthtalenium ions) with hydrogen peroxide.

Method for preparing adduct of butadiene polymer or copolymer and α, β-ethylenically unsaturated dicarboxylic acid compound

In a method for preparing an adduct of (A) a butadiene lower polymer or butadiene lower copolymer and (B) a α,β-ethylenically unsaturated dicarboxylic acid compound, said method is characterized in that said (A) and (B) are caused to react in the presence of one or more compounds selected from (C) p-phenylenediamine derivatives, catechol derivatives, pyrogallol derivatives, N-nitrosamines, quinoline derivatives and naphthol derivatives, thus serious increase of the viscosity of said adduct in the addition reaction can be prevented.