575-44-0

Basic information

• Product Name: 1,6-Dihydroxynaphthalene
• Synonyms: 1,6-NAPHTHALENEDIOL;1,6-DIHYDROXYNAPHTHALENE;2,5-DIHYDROXYNAPHTHALENE;2,5-Naphthalenediol;6-Hydroxy-1-naphthol;C.I. 76630;c.i.76630;Naphthalene, 1,6-dihydroxy-
• CAS NO: 575-44-0
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 209-386-7
• Product Categories: Intermediates of Dyes and Pigments;FINE Chemical & INTERMEDIATES;Naphthalene derivatives;API intermediates
• Mol File: 575-44-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 246.06°C (rough estimate)
• Flash Point: 193.545 °C
• Appearance: White to brown/Powder or Crystalline 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: very faint turbidity in Methanol
• PKA: 9.26±0.40(Predicted)
• BRN: 1939032
• CAS DataBase Reference: 1,6-Dihydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Dihydroxynaphthalene(575-44-0)
• EPA Substance Registry System: 1,6-Dihydroxynaphthalene(575-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: QJ4743333
• TSCA: Yes
• Hazardous Substances Data: 575-44-0(Hazardous Substances Data)

Usage

Chemical Properties

Beige powder

Purification Methods

Crystallise it from *benzene or *benzene/EtOH after treatment with charcoal. [Beilstein 6 IV 6557.]

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

Synthetic route

1,6-diacetoxynaphthalene (59335-81-8) → 1,6-dihydroxynaphthalene (575-44-0) + 1-acetoxy-6-hydroxynaphthalene + 6-acetoxy-1-hydroxynaphthalene

Conditions	Yield
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 0.75h; Hydrolysis; deacetylation;	A n/a B n/a C 54%

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%

5-aminonaphthalene-2-sulfonic acid (119-79-9) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
With sodium hydroxide at 260℃; unter Druck;

2-amino-5-hydroxy-naphthalene-1-sulfonic acid (871887-69-3) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
at 240℃; bei der Kalischmelze unter Druck;

5-amino-2-naphthol (86-97-5) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
With sodium hydrogensulfite anschliessendes Erhitzen mit wss. NaOH;

2-amino-1,5-naphthalenedisulfonic acid (117-62-4) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
at 240℃; bei der Kalischmelze unter Druck;
Multi-step reaction with 2 steps 1: durch Kalischmelze 2: 240 °C / bei der Kalischmelze unter Druck View Scheme

2,5-dihydroxy-naphthalene-1-sulfonic acid (858464-85-4) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
at 240℃; bei der Kalischmelze unter Druck;

naphthalene (91-20-3) → α-naphthol (90-15-3) + 1,6-dihydroxynaphthalene (575-44-0) + β-naphthol (135-19-3)

Conditions	Yield
With hydrogen fluoride; boron trifluoride; dihydrogen peroxide at -78℃; for 0.5h; Mechanism; Product distribution; other reagents, other temp.;

5-aminonaphthalene-2-sulfonic acid (119-79-9) + furan-2,3,5(4H)-trione pyridine (1:1) → 1,6-dihydroxynaphthalene (575-44-0) + 5-amino-2-naphthol (86-97-5) + 1-amino-naphthalene (134-32-7) + naphthol-(1)-sulfonic acid-(5)(?)

Conditions	Yield
at 260℃; im Autoklaven;

2-oxy-naphthalene-5-sulfonate potassium → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
With potassium carbonate at 260 - 270℃;

disulfurous acid ester of/the/ 1.6-dioxy-naphthalene-sulfonic acid-(5) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
With acid

naphthalene-disulfonic acid-(1.6) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
With alkali at 220 - 230℃;

6-hydroxy-1-naphthalene sulfonic acid (20386-27-0) + potash → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
at 260 - 270℃; beim Schmelzen;

naphthalene-1,6-disulfonic acid (525-37-1) + alkali → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
at 220 - 230℃;

2-amino-5-hydroxy-naphthalene-1-sulfonic acid (871887-69-3) + sodium hydrogensulfite + aniline (62-53-3) → 1,6-dihydroxynaphthalene (575-44-0) + 6-Anilino-[1]naphthol (139263-46-0) + 2,5-dihydroxy-naphthalene-1-sulfonic acid (858464-85-4) + 2-anilino-5-hydroxy-naphthalene-1-sulfonic acid (861341-81-3)

2,5-bis-sulfinooxy-naphthalene-1-sulfonic acid ; trisodium salt + acid → 1,6-dihydroxynaphthalene (575-44-0)

4,7-dihydroxy-naphthalene-1-sulfonic acid (149141-84-4) + sodium amalgam → 1,6-dihydroxynaphthalene (575-44-0)

sulfuric acid (7664-93-9) + 2-anilino-5-hydroxy-naphthalene-1-sulfonic acid (861341-81-3) → 1,6-dihydroxynaphthalene (575-44-0) + aniline (62-53-3)

2-aminonaphthalenesulfonic acid (81-16-3) → 1,6-dihydroxynaphthalene (575-44-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming sulfuric acid / 30 - 40 °C 2: 240 °C / bei der Kalischmelze unter Druck View Scheme
Multi-step reaction with 3 steps 1: fuming sulfuric acid / 30 - 40 °C 2: durch Kalischmelze 3: 240 °C / bei der Kalischmelze unter Druck View Scheme

1,6-dihydroxynaphthalene (575-44-0) + magnesium methyl carbonate (4861-79-4) → 1.6-Dihydroxy-2-naphthylcarbonsaeure (38134-93-9)

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

phthalic anhydride (85-44-9) + 1,6-dihydroxynaphthalene (575-44-0) → naphthofluorescein (61419-02-1)

Conditions	Yield
With methanesulfonic acid In acetone at 120℃; for 13h; Reagent/catalyst; Inert atmosphere;	99%
With methanesulfonic acid at 120℃; for 13h; Reagent/catalyst; Inert atmosphere;	87%
With methanesulfonic acid at 100℃; for 12h;	79%

1,6-dihydroxynaphthalene (575-44-0) + dimethyl sulfate (77-78-1) → 1,6-dimethoxynaphthalene (3900-49-0)

Conditions	Yield
With sodium hydroxide In ethanol; water at 45℃; for 1.5h; Inert atmosphere;	99%
With sodium hydroxide In acetone Heating;	94%
With potassium carbonate In acetone at 20℃; Inert atmosphere;	94%

1,6-dihydroxynaphthalene (575-44-0) + ethyl iodide (75-03-6) → Fmoc-(D,L)-5-ethoxy-2-aminotetraline-2-carboxylic acid (Fmoc-(D,L) 5-EtOAtc-OH) + 1,6-diethoxynaphthalene (3955-85-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	A 99% B 64%

1,6-dihydroxynaphthalene (575-44-0) + pivaloyl chloride (3282-30-2) → naphthalene-1,6-diyl bis(2,2-dimethylpropanoate) (1533457-80-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	99%

1,6-dihydroxynaphthalene (575-44-0) → 6-hydroxy-[1,4]naphthoquinone (4923-53-9)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene	97%
With C59H43N5OS2Zn; oxygen In methanol at 25℃; Irradiation;	92%
With methylene blue In methanol; water at 20℃; under 7500.75 Torr; for 0.266667h; Irradiation; Flow reactor;	89%

1-thiopropane (107-03-9) + 1,6-dihydroxynaphthalene (575-44-0) → 1,6-bis(1-propylthio)naphthalene

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Heating;	97%

1,6-dihydroxynaphthalene (575-44-0) + tetra-O-acetyl-β-D-xylopyranose (4049-33-6) → naphthalene-1,6-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;	95%

1,6-dihydroxynaphthalene (575-44-0) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → 12-(2-carboxyphenyl)-N,N-diethyl-8-hydroxy-3H-5-oxatetraphen-3-iminium

Conditions	Yield
With trifluoroacetic acid for 24h; Concentration; Reflux;	93%
With trifluoroacetic acid for 24h; Reflux;	93.2%
With trifluoroacetic acid at 90℃; for 6h;	61%

4-Nitrophthalonitrile (31643-49-9) + 1,6-dihydroxynaphthalene (575-44-0) → C26H12N4O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85 - 90℃; for 6h;	93%
With potassium carbonate In dimethyl sulfoxide for 24h; Ambient temperature;	53.4%

1,6-dihydroxynaphthalene (575-44-0) + butan-1-ol (71-36-3) → 6-butoxynaphth-1-ol (1335012-46-8) + 5-butoxynaphth-2-ol (1335012-43-5) + 1,6-dibutoxynaphthalene (1335012-45-7)

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 80℃; for 15h; Inert atmosphere;	A n/a B n/a C 92%

1,6-dihydroxynaphthalene (575-44-0) + 3-diethylaminophenol (91-68-9) → 9-diethylamino-2-hydroxy-benzo[a]phenoxazin-5-one (188712-75-6)

Conditions	Yield
Stage #1: 3-diethylaminophenol With hydrogenchloride; sodium nitrite In water at 0℃; for 2.66667h; Stage #2: 1,6-dihydroxynaphthalene In N,N-dimethyl-formamide for 3h; Reflux;	92%
In N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	56%
Stage #1: 3-diethylaminophenol With hydrogenchloride; sodium nitrite Stage #2: 1,6-dihydroxynaphthalene In N,N-dimethyl-formamide
Stage #1: 3-diethylaminophenol With hydrogenchloride; sodium nitrite In ethanol; water at 0 - 5℃; for 4h; Stage #2: 1,6-dihydroxynaphthalene In ethanol; water; N,N-dimethyl-formamide at 80℃; for 4h;

1-bromo-butane (109-65-9) + 1,6-dihydroxynaphthalene (575-44-0) → 1,6-dibutoxynaphthalene (1335012-45-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	92%

1,6-dihydroxynaphthalene (575-44-0) + 2,5-dicarboxy-5'-chloro-2',4'-dihydroxybenzophenone → 6-carboxy-2'-chloroseminaphthofluorescein

Conditions	Yield
With methanesulfonic acid for 14h; Heating;	91%

Benzylidenemalononitrile (2700-22-3) + 1,6-dihydroxynaphthalene (575-44-0) → 2,9-diamino-3,8-dicyano-4,7-diphenyl-4,7-dihydronaphtho<1,2-b:6,5-b'>dipyran (128405-18-5)

Conditions	Yield
With piperidine In ethanol for 1h; Heating;	90%

1,6-dihydroxynaphthalene (575-44-0) + 4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → 2-amino-4-(4-chlorophenyl)-8-hydroxy-4H-benzo[h]chromene-3-carbonitrile (179125-47-4)

Conditions	Yield
With nano zinc oxide In water at 80℃; for 4h; regioselective reaction;	90%

1,6-dihydroxynaphthalene (575-44-0) + methyl iodide (74-88-4) → 1,6-dimethoxynaphthalene (3900-49-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	90%

1-butanethiol (109-79-5) + 1,6-dihydroxynaphthalene (575-44-0) → 1,6-Bis-butylsulfanyl-naphthalene (127567-60-6)

Conditions	Yield
With trifluorormethanesulfonic acid at 30℃; for 3h;	88%

1,6-dihydroxynaphthalene (575-44-0) + dabsyl chloride (56512-49-3) → 1,6-dihydroxynaphthalene didabsylate (146303-78-8)

Conditions	Yield
With carbonate-bicarbonate buffer In acetone for 0.5h; Heating;	85%
With carbonate-bicarbonate buffer In acetone; acetonitrile 1.) 15 min, 2.) reflux;	85%

1,6-dihydroxynaphthalene (575-44-0) + dimethyl acetylenedicarboxylate (762-42-5) → (7-hydroxy-2-oxo-naphtho[1,2-b]furan-3-ylidene)-acetic acid methyl ester

Conditions	Yield
With pyridine In diethyl ether at 20℃; for 24h;	85%

1,6-dihydroxynaphthalene (575-44-0) + benzene (71-43-2) → 6-hydroxy-4-phenyl-1-tetralone (368883-85-6)

Conditions	Yield
With aluminum tri-bromide at 25℃; for 48h;	83%

S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulphonium tetrafluoroborate + 1,6-dihydroxynaphthalene (575-44-0) → 1,6-bis(monofluoromethoxy)naphthalene

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	82%

1,6-dihydroxynaphthalene (575-44-0) + 2-(2,4-dihydroxybenzoyl)benzoic acid (2513-33-9) → 3,10-dihydroxy-spiro[7H-benzo[c]xanthen-7,1'(3'H)-isobenzofuran]-3'-one

Conditions	Yield
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h;	82%
With methanesulfonic acid; trifluoroacetic acid at 80℃; for 24h;	82%
With methanesulfonic acid In toluene at 65℃; for 0.5h;	61%
Zinc chloride In methanol; potassium hydroxide; chloroform; water; acetic anhydride

1,11-dichloro-3,6,9-trioxaundecane (638-56-2) + 1,6-dihydroxynaphthalene (575-44-0) → 1,6-Bis-(2-{2-[2-(2-chloro-ethoxy)-ethoxy]-ethoxy}-ethoxy)-naphthalene (185246-97-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Heating;	81%

1,6-dihydroxynaphthalene (575-44-0) → 6-Hydroxy-1-tetralone (3470-50-6)

Conditions	Yield
With aluminum tri-bromide; cyclohexane In various solvent(s) at 25℃; for 72h;	80%
With sodium hydroxide; aluminum nickel Hydrogenation;
With sodium hydroxide; nickel Hydrogenation;

1,6-dihydroxynaphthalene (575-44-0) → 2,6-dihydroxynaphthalene-1,4-dione (31039-62-0)

Conditions	Yield
With KO2 In toluene at -10℃; for 6h;	80%

2-(8-hydroxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbonyl)benzoic acid (107070-67-7) + 1,6-dihydroxynaphthalene (575-44-0) → C30H23NO4

Conditions	Yield
Stage #1: 2-(8-hydroxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbonyl)benzoic acid; 1,6-dihydroxynaphthalene With methanesulfonic acid at 65℃; for 12h; Stage #2: With sodium perchlorate In water at 80℃;	79.6%

1,6-dihydroxynaphthalene (575-44-0) + 3-(ethyl(3-hydroxy-4-nitrosophenyl)amino)propane-1-sulfonic acid hydrochloride (915777-42-3) → 3-(ethyl(2-hydroxy-5-oxo-5H-benzo[a]phenoxazin-9-yl)amino)propane-1-sulfonic acid (188712-82-5)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Heating;	79%
In N,N-dimethyl-formamide at 150℃; for 4h; Inert atmosphere;	0.56 g

1,6-dihydroxynaphthalene (575-44-0) + 2-(2,4-dihydroxy-3-methyl-benzoyl)-benzoic acid (109342-74-7) → 4-methyl-3,10-dihydroxy-spiro[7H-benzo[c]xanthen-7,1'(3'H)-isobenzofuran]-3'-one

Conditions	Yield
In methanesulfonic acid; water	79%

1,6-dihydroxynaphthalene (575-44-0) + 4-(2,4-dihydroxybenzoyl)isophthalic acid → C25H14O7

Conditions	Yield
With methanesulfonic acid; trifluoroacetic acid at 20℃; for 24h; regioselective reaction;	79%
With methanesulfonic acid; trifluoroacetic acid at 20℃;

Upstream product

• 871887-69-3 2-amino-5-hydroxy-naphthalene-1-sulfonic acid 
• 135-19-3 β-naphthol 
• 119-79-9 5-aminonaphthalene-2-sulfonic acid 
• 81-16-3 2-aminonaphthalenesulfonic acid 
• 7664-93-9 sulfuric acid 
• 861341-81-3 2-anilino-5-hydroxy-naphthalene-1-sulfonic acid 
• 149141-84-4 4,7-dihydroxy-naphthalene-1-sulfonic acid 
• 62-53-3 aniline 
• 525-37-1 naphthalene-1,6-disulfonic acid 
• 20386-27-0 6-hydroxy-1-naphthalene sulfonic acid 
• 59335-81-8 1,6-diacetoxynaphthalene 
• 91-20-3 naphthalene 
• 858464-85-4 2,5-dihydroxy-naphthalene-1-sulfonic acid 
• 117-62-4 2-amino-1,5-naphthalenedisulfonic acid 

Downstream Products

• 146303-78-8 1,6-dihydroxynaphthalene didabsylate 
• 38134-93-9 1.6-Dihydroxy-2-naphthylcarbonsaeure 
• 607-20-5 hydroxy-6 naphthoquinone-1,2 
• 31039-62-0 2,6-dihydroxynaphthalene-1,4-dione 
• 32178-63-5 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid 
• 133546-47-1 naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole 
• 188712-75-6 9-diethylamino-2-hydroxy-benzo[a]phenoxazin-5-one 
• 32263-72-2 6-(benzyloxy)naphthalen-1-ol 
• 185247-03-4 5-(benzyloxy)naphthalen-2-ol 
• 1196990-94-9 1,6-bis[4-(4-n-tetradecyloxybenzoyloxy)benzoyloxy]naphthalene 
• 1269512-11-9 C₅₈H₅₀N₂O₈S₂ 
• 59335-81-8 1,6-diacetoxynaphthalene 
• 64523-77-9 1,6-Bis-diphenoxymethoxy-naphthalene 

Relevant articles and documents

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.

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.

Cyclic monocarbonate bishaloformates

Cyclic monocarbonate bischloroformates are prepared by the reaction of a carbonyl halide such as phosgene with a bridged substituted resorcinol or hydroquinone such as bis(2,4-dihydroxy-3-methylphenyl)methane or bis(2,5-dihydroxy-3,4,6-trimethylphenyl)methane in the presence of aqueous alkali metal hydroxide. The cyclic monocarbonate bischloroformates may be used for the preparation of linear or cyclic polycarbonates containing cyclic carbonate structural units, which may in turn be converted to crosslinked polycarbonates.