2,7-Dihydroxynaphthalene supplier

Name
2,7-Dihydroxynaphthalene
EINECS 209-478-7
CAS No. 582-17-2
Article Data33
CAS DataBase
Density 1.33 g/cm³
Solubility insoluble in hot water
Melting Point 185-190 °C(lit.)
Formula C₁₀H₈O₂
Boiling Point 375.4 °C at 760 mmHg
Molecular Weight 160.172
Flash Point 193.5 °C
Transport Information
Appearance Light yellow to grey needle crystal
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms CI 76645;2,7-Naphthalenediol (8CI,9CI);Naphthalene-2,7-diol;2,7-naphthalenediol;C.I. 76645;Naphthalenediol-2,7 [French];
PSA 40.46000
LogP 2.25100

Synthetic route

: 2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-naphthalene

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 40458-98-8
2,7-diisopropylnaphthalene

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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%

: 145970-32-7
7‐((tert‐butyldimethylsilyl)oxy)naphthalen‐2‐ol

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 20258-95-1
2,7-dihydroxynaphthalene-1-carbaldehyde

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 526190-47-6
2,7-bis(diethylcarbamoyloxy)naphthalene

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 1655-35-2, 51770-81-1
2,7-naphthalenedisulfonic acid, sodium salt

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 40458-98-8
2,7-diisopropylnaphthalene

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 760179-65-5
7-isopropylnaphthalen-2-ol

Conditions

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%

: 22472-26-0
2,7-diacetoxynaphthalene

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 146744-23-2
2-acetoxy-7-hydroxynaphthalene

Conditions

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

: 25932-69-8
2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure

: 108-46-3
recorcinol

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 2321-07-5
fluorescein

Conditions

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

...Expand

: 81803-62-5
8-bromo-2,7-dihydroxynaphthalene-1-carbaldehyde

A: 20258-95-1
2,7-dihydroxynaphthalene-1-carbaldehyde

B: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 135-19-3
β-naphthol

A: 581-43-1
2,6-Dihydroxynaphthalene

B: 575-38-2
1,7-Dihydroxynaphthalene

C: 575-44-0
1,6-dihydroxynaphthalene

D: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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%

...Expand

: 56-23-5
tetrachloromethane

: 92-40-0
2-hydroxynaphthalene-7-sulfonic acid

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
beim Schmelzen;

: 317807-18-4
(±)-2,2’,7,7’-tetrahydroxy-1,1’-binaphthyl

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
at 300℃;

: 92-40-0
2-hydroxynaphthalene-7-sulfonic acid

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
With sodium hydroxide beim Schmelzen;

: 92-41-1
2,7-naphthalenedisulfonic acid

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
With potassium hydroxide

: 58933-28-1
9,11-dihydroxy-2-methoxy-benzo[a]xanthen-12-one

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
With potassium hydroxide

: C102H144N4O44*C10H8O2

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 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

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

: C50H60O12*2C10H8O2

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 202195-93-5
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

Conditions

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

: 91-20-3
naphthalene

A: 571-60-8
1,4-Dihydroxynaphthalene

B: 90-15-3
α-naphthol

C: 582-17-2
2,7-Dihydroxynaphthalene

D: 569-42-6
1,8-dihydroxynaphthalene

E: 83-56-7
1,5-dihydroxynaphthalene

F: 135-19-3
β-naphthol

G all disubstituted naphthalenes; trisubstituted naphthalenes: all disubstituted naphthalenes; trisubstituted naphthalenes

Conditions

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;

...Expand

: 92-41-1
2,7-naphthalenedisulfonic acid

alkali hydroxide: alkali hydroxide

: 582-17-2
2,7-Dihydroxynaphthalene

disodium-: disodium-

calcium-: calcium-

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

Conditions	Yield
With potassium hydroxide
With sodium hydroxide

naphthalene-2.7-disulfonate calcium: naphthalene-2.7-disulfonate calcium

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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: naphthalene-2.7-disulfonate sodium

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 533933-41-4
C16H16N2O6

Conditions

Conditions	Yield
In chloroform at 24.85℃; Equilibrium constant;

: 81803-62-5
8-bromo-2,7-dihydroxynaphthalene-1-carbaldehyde

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 5060-82-2
7-methoxy-2-naphthol

: 582-17-2
2,7-Dihydroxynaphthalene

Conditions

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

: 1368254-78-7
C14H15BrO4

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 2321-07-5
fluorescein

Conditions

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

: 1368254-79-8
C22H20O7

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 2321-07-5
fluorescein

Conditions

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

: 2954-75-8
1-bromo-2,7-dihydroxynaphthalene

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 2321-07-5
fluorescein

Conditions

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

: 75-77-4
chloro-trimethyl-silane

: 582-17-2
2,7-Dihydroxynaphthalene

: 1226-72-8
2,7-bis(trimethylsilyloxy)naphthalene

Conditions

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

: 582-17-2
2,7-Dihydroxynaphthalene

: 27428-79-1
1-nitroso-naphthalene-2,7-diol

Conditions

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%

: 582-17-2
2,7-Dihydroxynaphthalene

: 162934-16-9
ethyl 6-O-(tert-butyldiphenylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 2,7-bis-(ethyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl-4-oxy)naphthalene

Conditions

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

: 582-17-2
2,7-Dihydroxynaphthalene

: 77-78-1
dimethyl sulfate

: 3469-26-9
2,7-Dimethoxynaphthalene

Conditions

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

: 582-17-2
2,7-Dihydroxynaphthalene

: 2954-75-8
1-bromo-2,7-dihydroxynaphthalene

Conditions

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%

: 638-07-3
ethyl (2-chloroaceto)acetate

: 582-17-2
2,7-Dihydroxynaphthalene

: 861820-83-9
1-chloromethyl-9-hydroxy-3-oxo-3H-benzo[f]benzopyran

Conditions

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%

: 1072-67-9
5-methylisoxazol-3-ylamine

: 582-17-2
2,7-Dihydroxynaphthalene

: 459-57-4
4-fluorobenzaldehyde

: 1380601-72-8
C21H17FN2O3

Conditions

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

...Expand

: 31643-49-9
4-Nitrophthalonitrile

: 582-17-2
2,7-Dihydroxynaphthalene

: 77785-81-0
2,7-Bis(3,4-Dicyanophenoxy)Naphthalene

Conditions

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%)

: 1072-67-9
5-methylisoxazol-3-ylamine

: 582-17-2
2,7-Dihydroxynaphthalene

: 555-16-8
4-nitrobenzaldehdye

: 1380601-75-1
1-[(5-methylisoxazol-3-ylamino)(4-nitrophenyl)methyl]naphthalene-2,7-diol

Conditions

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

...Expand

: 582-17-2
2,7-Dihydroxynaphthalene

: 88-10-8
N,N-diethylcarbamyl chloride

: 526190-47-6
2,7-bis(diethylcarbamoyloxy)naphthalene

Conditions

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

: 582-17-2
2,7-Dihydroxynaphthalene

: 90800-48-9
1-nitro-2,7-dihydroxynaphthalene

Conditions

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

: 582-17-2
2,7-Dihydroxynaphthalene

: 317807-18-4
(±)-2,2’,7,7’-tetrahydroxy-1,1’-binaphthyl

Conditions

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%

: 582-17-2
2,7-Dihydroxynaphthalene

: 108-24-7
acetic anhydride

: 22472-26-0
2,7-diacetoxynaphthalene

Conditions

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;

: 582-17-2
2,7-Dihydroxynaphthalene

: 459-57-4
4-fluorobenzaldehyde

: 126-81-8
dimedone

: 1352090-35-7
12-(4-fluorophenyl)-2-hydroxy-9,9-dimethyl-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one

Conditions

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%

...Expand

: 110-85-0
piperazine

: 50-00-0
formaldehyd

: 582-17-2
2,7-Dihydroxynaphthalene

: 1,1′-[piperazine-1,4-diylbis(methylene)]bis(naphthalene-2,7-diol)

Conditions

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%

...Expand

2,7-Dihydroxynaphthalene Consensus Reports

Reported in EPA TSCA Inventory.

2,7-Dihydroxynaphthalene Specification

The CAS register number of 2,7-Naphthalenediol is 582-17-2. It also can be called as 2,7-Dihydroxynaphthalene and the IUPAC name about this chemical is naphthalene-2,7-diol. The molecular formula about this chemical is C₁₀H₈O₂and the molecular weight is 160.17. It belongs to the following product categories, such as Fine Chemical & Intermediates; Aromatics; API intermediates and so on. This chemical can be used as dye and medicine intermediate. In the air, the solution will quickly become deeper.

Physical properties about 2,7-Naphthalenediol are: (1)ACD/LogP: 1.98; (2)ACD/LogD (pH 5.5): 1.98; (3)ACD/LogD (pH 7.4): 1.97; (4)ACD/BCF (pH 5.5): 18.7; (5)ACD/BCF (pH 7.4): 18.38; (6)ACD/KOC (pH 5.5): 283.16; (7)ACD/KOC (pH 7.4): 278.21; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 18.46 Å²; (12)Index of Refraction: 1.725; (13)Molar Refractivity: 47.85 cm³; (14)Molar Volume: 120.4 cm³; (15)Polarizability: 18.97x10^-24cm³; (16)Surface Tension: 64.4 dyne/cm; (17)Enthalpy of Vaporization: 64.73 kJ/mol; (18)Boiling Point: 375.4 °C at 760 mmHg; (19)Vapour Pressure: 3.62E-06 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,7-dihydroxy-[1]naphthaldehyde. This reaction will need reagent hydrogen chloride and solvent ethanol. The reaction time is 30 min. The yield is about 82%.

Uses of 2,7-Naphthalenediol: it can be used to produce 1-nitroso-naphthalene-2,7-diol. This reaction will need reagent hydrochloric acid and NaNO₂.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1cc2c(cc1)ccc(O)c2
(2)InChI: InChI=1/C10H8O2/c11-9-3-1-7-2-4-10(12)6-8(7)5-9/h1-6,11-12H
(3)InChIKey: DFQICHCWIIJABH-UHFFFAOYAV
(4)Std. InChI: InChI=1S/C10H8O2/c11-9-3-1-7-2-4-10(12)6-8(7)5-9/h1-6,11-12H
(5)Std. InChIKey: DFQICHCWIIJABH-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	102mg/kg (102mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 13, Pg. 381, 1978.

Product Name

2,7-Dihydroxynaphthalene

Synthetic route

2,7-Dihydroxynaphthalene Consensus Reports

2,7-Dihydroxynaphthalene Specification

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