582-17-2

Basic information

• Product Name: 2,7-Dihydroxynaphthalene
• Synonyms: C.I. 76645;c.i.76645;CI 76645;Naphthalene-2,7-Diol;Naphthalenediol-(2,7);naphthalenediol-2,7;2,7-DIHYDROXYNAPTHALENE;2,7-DIHYDROXYNAPHTHALENE
• CAS NO: 582-17-2
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 209-478-7
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatics;API intermediates;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 582-17-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 185-190 °C(lit.)
• Boiling Point: 246.06°C (rough estimate)
• Flash Point: 193.5 °C
• Appearance: Gray/Powder
• Density: 1.0924 (rough estimate)
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Refractive Index: 1.5418 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.14±0.40(Predicted)
• Water Solubility: insoluble
• BRN: 2042383
• CAS DataBase Reference: 2,7-Dihydroxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dihydroxynaphthalene(582-17-2)
• EPA Substance Registry System: 2,7-Dihydroxynaphthalene(582-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: QJ4780000
• TSCA: Yes
• Hazardous Substances Data: 582-17-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to grey needle crystal

Uses

Different sources of media describe the Uses of 582-17-2 differently. You can refer to the following data:
1. 2,7-Dihydroxynaphthalene can be used as starting material for the synthesis of sulfonic acids and divinylnaphthalenes.
2. 2,7-Dihydroxynaphthalene is a reagent used in the preparation of monomers of high carbon materials. Also used in the synthesis of splitomicin analogues.
3. 2,7-Naphthalenediol is a reagent used in the preparation of monomers of high carbon materials. Also used in the synthesis of splitomicin analogues.

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

Synthetic route

2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-naphthalene → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With iron(III) chloride In methanol at 60℃; for 6h;	95%

2,7-diisopropylnaphthalene (40458-98-8) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
Stage #1: 2,7-diisopropylnaphthalene With N-hydroxyphthalimide; azobisisobutyronitrile; oxygen In acetonitrile at 75℃; under 15201 Torr; for 21h; Stage #2: With sulfuric acid In acetonitrile at 25℃; for 2h; Further stages.;	90%

7‐((tert‐butyldimethylsilyl)oxy)naphthalen‐2‐ol (145970-32-7) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With iron(III) chloride In methanol at 60℃; for 6h;	90%

2,7-dihydroxynaphthalene-1-carbaldehyde (20258-95-1) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With hydrogenchloride In ethanol for 0.5h;	82%
Multi-step reaction with 2 steps 1: 52 percent / Br2 / pyridine / 1 h 2: 20 percent / hydrogen chloride / ethanol / 0.5 h View Scheme

2,7-bis(diethylcarbamoyloxy)naphthalene (526190-47-6) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With zirconocene dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	82%

2,7-naphthalenedisulfonic acid, sodium salt (1655-35-2, 51770-81-1) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With sodium oxide; sodium hydroxide In dodecane at 290℃; for 8h; Solvent; Temperature; Autoclave;	77.1%

2,7-diisopropylnaphthalene (40458-98-8) → 2,7-Dihydroxynaphthalene (582-17-2) + 7-isopropylnaphthalen-2-ol (760179-65-5)

Conditions	Yield
Stage #1: 2,7-diisopropylnaphthalene With N-hydroxyphthalimide; azobisisobutyronitrile; oxygen In acetonitrile at 75℃; under 760.051 Torr; for 21h; Stage #2: With sulfuric acid In acetonitrile at 25℃; for 2h; Further stages.;	A 67% B 21%

2,7-diacetoxynaphthalene (22472-26-0) → 2,7-Dihydroxynaphthalene (582-17-2) + 2-acetoxy-7-hydroxynaphthalene (146744-23-2)

Conditions	Yield
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 1h; Hydrolysis; deacetylation;	A n/a B 45%

2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure (25932-69-8) + recorcinol (108-46-3) → 2,7-Dihydroxynaphthalene (582-17-2) + fluorescein (2321-07-5)

Conditions	Yield
With methanesulfonic acid In toluene	A 43% B 20%

8-bromo-2,7-dihydroxynaphthalene-1-carbaldehyde (81803-62-5) → 2,7-dihydroxynaphthalene-1-carbaldehyde (20258-95-1) + 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With hydrogenchloride In ethanol for 0.5h;	A 35% B 20%

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%

tetrachloromethane (56-23-5) + 2-hydroxynaphthalene-7-sulfonic acid (92-40-0) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
beim Schmelzen;

(±)-2,2’,7,7’-tetrahydroxy-1,1’-binaphthyl (317807-18-4) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
at 300℃;

2-hydroxynaphthalene-7-sulfonic acid (92-40-0) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With sodium hydroxide beim Schmelzen;

2,7-naphthalenedisulfonic acid (92-41-1) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With potassium hydroxide

9,11-dihydroxy-2-methoxy-benzo[a]xanthen-12-one (58933-28-1) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With potassium hydroxide

C102H144N4O44*C10H8O2 → 2,7-Dihydroxynaphthalene (582-17-2) + 3,3I,3II,3III,3IV,3V,3VI,3VII,3VIII,3IX,3X,3XI-[(5,14,20,29,32,33,36,37-octamethyl-7,12,22,27-tetraoxapentacyclo[26.2.2.23,6.213,16.218,21]octatriaconta-3,5,13,15,18,20,28,30,31,33,35,37-dodecaene-2,2,17,17-tetrayl)tetra...]

Conditions	Yield
In dimethylsulfoxide-d6; water-d2 at 26.9℃; Equilibrium constant; 1H-NMR binding titration method;

C50H60O12*2C10H8O2 → 2,7-Dihydroxynaphthalene (582-17-2) + 5,14,20,21,29,32,33,37-octamethyl-7,12,22,27-tetraoxapentacyclo[26.2.2.23,6.213,16.218,21]octatriaconta-3,5,13,15,18,20,28,30,31,33,35,37-dodecaene-2,2,17,17-tetraacetic acid (202195-93-5)

Conditions	Yield
In dimethylsulfoxide-d6; water-d2 at 26.9℃; Equilibrium constant; 1H-NMR binding titration method;

naphthalene (91-20-3) → 1,4-Dihydroxynaphthalene (571-60-8) + α-naphthol (90-15-3) + 2,7-Dihydroxynaphthalene (582-17-2) + 1,8-dihydroxynaphthalene (569-42-6) + 1,5-dihydroxynaphthalene (83-56-7) + β-naphthol (135-19-3) + all disubstituted naphthalenes; trisubstituted naphthalenes

Conditions	Yield
With n-butyllithium; potassium tert-butylate Product distribution; multistep reaction; isomer distribution as a function of the solvent and conditions (THF only monosubstitution), also after reaction with Me2SO4;

2,7-naphthalenedisulfonic acid (92-41-1) + alkali hydroxide → 2,7-Dihydroxynaphthalene (582-17-2)

disodium- + calcium- → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With potassium hydroxide
With sodium hydroxide

naphthalene-2.7-disulfonate calcium → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With sodium hydroxide; hydrogen at 290 - 300℃; man saeuert die Schmelze mit Salzsaeure an und schuettelt mit Aether oder Essigester aus;

naphthalene-2.7-disulfonate sodium → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With sodium hydroxide; hydrogen at 290 - 300℃; man saeuert die Schmelze mit Salzsaeure an und schuettelt mit Aether oder Essigester aus;

C16H16N2O6*C10H8O2 → 2,7-Dihydroxynaphthalene (582-17-2) + C16H16N2O6 (533933-41-4)

Conditions	Yield
In chloroform at 24.85℃; Equilibrium constant;

8-bromo-2,7-dihydroxynaphthalene-1-carbaldehyde (81803-62-5) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / hydrogen chloride / ethanol / 0.5 h 2: 82 percent / hydrogen chloride / ethanol / 0.5 h View Scheme

7-methoxy-2-naphthol (5060-82-2) → 2,7-Dihydroxynaphthalene (582-17-2)

Conditions	Yield
With Pyridine hydrobromide In sulfolane at 150 - 160℃; for 3h; Inert atmosphere;

C14H15BrO4 (1368254-78-7) → 2,7-Dihydroxynaphthalene (582-17-2) + fluorescein (2321-07-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 3.5 h / -78 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 3.1: methanesulfonic acid / toluene View Scheme

C22H20O7 (1368254-79-8) → 2,7-Dihydroxynaphthalene (582-17-2) + fluorescein (2321-07-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 2: methanesulfonic acid / toluene View Scheme

1-bromo-2,7-dihydroxynaphthalene (2954-75-8) → 2,7-Dihydroxynaphthalene (582-17-2) + fluorescein (2321-07-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice 1.2: 4.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 3.5 h / -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 4.1: methanesulfonic acid / toluene View Scheme

chloro-trimethyl-silane (75-77-4) + 2,7-Dihydroxynaphthalene (582-17-2) → 2,7-bis(trimethylsilyloxy)naphthalene (1226-72-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	99%
With pyridine; diethyl ether

2,7-Dihydroxynaphthalene (582-17-2) → 1-nitroso-naphthalene-2,7-diol (27428-79-1)

Conditions	Yield
With sulfuric acid; sodium hydroxide; sodium nitrite In water at 0℃;	99%
With sulfuric acid; sodium hydroxide; sodium nitrite In water at 3℃; for 1.5h; Temperature;	94%
With sodium nitrite	92.1%

2,7-Dihydroxynaphthalene (582-17-2) + ethyl 6-O-(tert-butyldiphenylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (162934-16-9) → 2,7-bis-(ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-4-oxy)naphthalene

Conditions	Yield
tris-(dibenzylideneacetone)dipalladium(0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 25℃; for 20h;	99%

2,7-Dihydroxynaphthalene (582-17-2) + dimethyl sulfate (77-78-1) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With potassium carbonate In acetone for 10h; Reflux;	98.3%
With sodium hydroxide	97%
With sodium hydroxide for 2h;	96.5%

2,7-Dihydroxynaphthalene (582-17-2) → 1-bromo-2,7-dihydroxynaphthalene (2954-75-8)

Conditions	Yield
With N-Bromosuccinimide; lithium perchlorate; silica gel In dichloromethane at 20℃; for 0.0833333h;	98%
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h;	96%
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;	95%

ethyl (2-chloroaceto)acetate (638-07-3) + 2,7-Dihydroxynaphthalene (582-17-2) → 1-chloromethyl-9-hydroxy-3-oxo-3H-benzo[f]benzopyran (861820-83-9)

Conditions	Yield
With sulfuric acid at 20℃; for 3h;	98%
In sulfuric acid at 20℃; Pechmann reaction;	92%
With sulfuric acid In water at 20℃; for 78h;	92%

5-methylisoxazol-3-ylamine (1072-67-9) + 2,7-Dihydroxynaphthalene (582-17-2) + 4-fluorobenzaldehyde (459-57-4) → C21H17FN2O3 (1380601-72-8)

Conditions	Yield
at 80℃; for 0.5h; Neat (no solvent);	98%

4-Nitrophthalonitrile (31643-49-9) + 2,7-Dihydroxynaphthalene (582-17-2) → 2,7-Bis(3,4-Dicyanophenoxy)Naphthalene (77785-81-0)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide for 24h; Ambient temperature;	97%
With sodium hydroxide; dimethyl sulfoxide In water; benzene	6.1 g (59%)

5-methylisoxazol-3-ylamine (1072-67-9) + 2,7-Dihydroxynaphthalene (582-17-2) + 4-nitrobenzaldehdye (555-16-8) → 1-[(5-methylisoxazol-3-ylamino)(4-nitrophenyl)methyl]naphthalene-2,7-diol (1380601-75-1)

Conditions	Yield
at 80℃; for 0.5h; Neat (no solvent);	97%

2,7-Dihydroxynaphthalene (582-17-2) + N,N-diethylcarbamyl chloride (88-10-8) → 2,7-bis(diethylcarbamoyloxy)naphthalene (526190-47-6)

Conditions	Yield
With pyridine at 100℃; for 48h; Inert atmosphere; Cooling with ice;	97%
With pyridine at 100℃; for 48h;

2,7-Dihydroxynaphthalene (582-17-2) → 1-nitro-2,7-dihydroxynaphthalene (90800-48-9)

Conditions	Yield
Stage #1: 2,7-Dihydroxynaphthalene With sodium hydroxide In water at 60℃; for 0.5h; Stage #2: With sulfuric acid; sodium nitrite In water at 0℃; for 3h;	96.2%
With sulfuric acid; sodium hydroxide; sodium nitrite at 0℃; for 1h;	90%
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In diethyl ether for 2h; Ambient temperature;	50%
Multi-step reaction with 3 steps 1: KOH / H2O 2: aq. HNO3 / acetic acid 3: Py*HCl / Heating View Scheme

2,7-Dihydroxynaphthalene (582-17-2) → (±)-2,2’,7,7’-tetrahydroxy-1,1’-binaphthyl (317807-18-4)

Conditions	Yield
With iron(III) chloride In water for 4h; Heating;	96%
With iron(III) chloride In water for 4h; Reflux;	96%
With air; aluminum oxide; copper(II) sulfate In chlorobenzene at 140℃; for 15h;	93%

2,7-Dihydroxynaphthalene (582-17-2) + acetic anhydride (108-24-7) → 2,7-diacetoxynaphthalene (22472-26-0)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	96%
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane for 2h; Ambient temperature;	82%
With pyridine
With pyridine Acetylation; esterification;

2,7-Dihydroxynaphthalene (582-17-2) + 4-fluorobenzaldehyde (459-57-4) + dimedone (126-81-8) → 12-(4-fluorophenyl)-2-hydroxy-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one (1352090-35-7)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 2.5h; Reflux;	96%
With N-methyl-2-oxopyrrolidin-1-ium dihydrogen phosphate at 80℃; for 0.333333h; Ionic liquid;	91%
With alum at 60℃; for 0.833333h; Green chemistry;	82%

piperazine (110-85-0) + formaldehyd (50-00-0) + 2,7-Dihydroxynaphthalene (582-17-2) → 1,1′-[piperazine-1,4-diylbis(methylene)]bis(naphthalene-2,7-diol)

Conditions	Yield
In methanol; water at 20℃; for 1.33333h;	96%
Stage #1: piperazine; formaldehyd In methanol at 20℃; for 0.333333h; Stage #2: 2,7-Dihydroxynaphthalene In methanol for 2h;	96%

Upstream product

• 56-23-5 tetrachloromethane 
• 92-40-0 2-hydroxynaphthalene-7-sulfonic acid 
• 317807-18-4 (±)-2,2’,7,7’-tetrahydroxy-1,1’-binaphthyl 
• 81803-62-5 8-bromo-2,7-dihydroxynaphthalene-1-carbaldehyde 
• 58933-28-1 9,11-dihydroxy-2-methoxy-benzo[a]xanthen-12-one 
• 178161-06-3 2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-naphthalene 
• 5060-82-2 7-methoxy-2-naphthol 
• 1655-35-2 2,7-naphthalenedisulfonic acid, sodium salt 
• 107-30-2 chloromethyl methyl ether 
• 1418216-10-0 C₁₅H₁₆O₅ 
• 526190-47-6 2,7-bis(diethylcarbamoyloxy)naphthalene 
• 25932-69-8 2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure 
• 108-46-3 recorcinol 
• 2954-75-8 1-bromo-2,7-dihydroxynaphthalene 

Downstream Products

• 66947-01-1 6-hydroxy-7-phenyl-phenalen-1-one 
• 132046-04-9 1-phenylazo-naphthalene-2,7-diol 
• 6363-82-2 9-dimethylamino-2-hydroxy-benzo[a]phenoxazinylium; chloride 
• 20917-99-1 Dekalindiol-(2,7) 
• 96965-79-6 2,7-dibromo-3,6-dihydroxy naphthalene 
• 3024-25-7 dihydroxy-2,7 dichloro-1,8 naphtalene 
• 91192-54-0 1,1,8-trichloro-7-hydroxy-1H-naphthalen-2-one 
• 613-76-3 2,7-diaminonaphthalene 
• 93-36-7 2-amino-7-hydroxynaphthalene 
• 23894-07-7 3,6-dihydroxynaphthalene-2,7-disulfonic acid 
• 6471-45-0 N,N'-di-p-tolyl-naphthalene-2,7-diyldiamine 
• 118495-07-1 7-(benzyloxy)-2-naphthol 
• 93245-52-4 2,7-bis(benzyloxy)naphthalene 
• 241475-06-9 N,N’-bis(4-methoxyphenyl)-2,7-naphthalenediamine 

Relevant articles and documents

Method for synthesizing 2,7-dioxynaphthalene

The invention relates to a method for synthesizing 2,7-dioxynaphthalene. The method comprises the following steps: adding 2,7-naphthyldisulfnate, sodium hydroxide, sodium oxide and a solvent into a high-pressure kettle; then heating to the temperature of 260-350 DEG C and carrying out stirring reaction at the temperature; cooling the obtained solution to a room temperature while stirring; after filtering, neutralizing a filter cake by using a sulfuric acid solution to PH 0-4; and filtering and drying the obtained suspension to obtain the final product. Compared with an existing method, the method uses a mixed alkali fusion reagent consisting of sodium hydroxide and sodium oxide to replace traditional independently used sodium hydroxide, the use amount of the sodium hydroxide is greatly reduced, enrichment of water in a reaction system is avoided, therefore, the generation amount of an alkali fusion by-product is reduced remarkably, and the yield of the 2,7-dioxynaphthalene is high.

Reductive cleavage of aryl O-carbamates to phenols by the Schwartz reagent. Expedient link to the directed ortho metalation strategy?

A general, mild, and efficient method for the reductive cleavage of aryl O-carbamates to phenols, 1 → 2 using the Schwartz reagent is reported. The method is selective, tolerating a large number of functional groups; may be carried out by direct or by an economical in situ procedure; and, notably, establishes a synthetic connection to the directed ortho metalation strategy (Figure 1) allowing new entries into difficult to prepare contiguously substituted aromatics and heteroaromatics.

Highly efficient and scalable process for demethylation of 6-(2,4-dimethoxybenzoyl)chromen-2-one and other aryl methyl ethers

Demethylation of 6-(2,4-dimethoxybenzoyl)chromen-2-one and some other aryl methyl ethers was achieved with pyridinium bromide as demethylating agent and sulfolane as solvent. Compared with other demethylation methods, this combination offers advantages of clean conversion, excellent yields, easy operation and workup, and manageable reaction temperatures. This process could be particularly useful for large-scale production because it avoids use of corrosive or moisture-sensitive reagents. Copyright