575-38-2

Basic information

• Product Name: 1,7-Dihydroxynaphthalene
• Synonyms: c.i.76635;1,7-DIHYDROXYNAPHTHALENE;1,7-NAPHTHALENEDIOL;naphthalene-1,7-diol;1,7-Napthalenediol;1,7-NAPHTHALENEDIOL 97%;1,7-DihydroxylNaphthalene;1,7-Dihydroxynaphthalin
• CAS NO: 575-38-2
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 209-383-0
• Product Categories: Intermediates of Dyes and Pigments;FINE Chemical & INTERMEDIATES;Naphthalene derivatives;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 575-38-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 180-184 °C(lit.)
• Boiling Point: 246.06°C (rough estimate)
• Flash Point: 252 °C
• Appearance: Yellowish to white powder
• Density: 1.0924 (rough estimate)
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Refractive Index: 1.5418 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.58±0.40(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 1908499
• CAS DataBase Reference: 1,7-Dihydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-Dihydroxynaphthalene(575-38-2)
• EPA Substance Registry System: 1,7-Dihydroxynaphthalene(575-38-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-36/37
• WGK Germany: 2
• RTECS: QJ4746666
• TSCA: Yes
• Hazardous Substances Data: 575-38-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish to white powder

Uses

The preparation of 1,7-Dihydroxynaphthalene and its prompt characterization from its NMR data and peculiarities. Removal of dihydroxynaphthalenes from aqueous solution with the aid of an oxidoreductase polyphenol oxidase and biopolymer chitosan.

Application

1,7-Dihydroxynaphthalene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

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

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

Downstream Products

• 4923-53-9 6-hydroxy-[1,4]naphthoquinone 
• 93831-53-9 naphthalene-1,7-diyl bisphenylacetate 
• 51850-49-8 1,7-diacetoxynaphthalene 
• 5309-18-2 1,7-dimethoxynaphthalene 
• 150712-58-6 1-acetoxy-7-methoxynaphthalene 
• 67247-13-6 7-methoxynaphth-1-ol 
• 91344-50-2 8-methoxy-naphthalen-2-ol 
• 22009-38-7 7-hydroxy-1-tetralone 
• 112948-02-4 8-cyclohexyl-3-hydroxy-7,8,9,10-tetrahydro-dibenzo[c,h]chromen-6-one 
• 371972-18-8 cyclo[bis(naphthalene-1,7-diyl dimethylamidophosphite)] 
• 99645-27-9 9-diethylamino-3-(p-decyloxybenzoyloxy)benzophenoxazin-5-one 
• 1050414-41-9 naphthalene-1,7-diyl bis(4-formylbenzoate) 
• 1269512-13-1 C₅₈H₅₀N₂O₈S₂ 

Relevant articles and documents

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