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1,1'-Bi-2-naphthol
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Name

1,1'-Bi-2-naphthol

 EINECS 210-014-0
CAS No. 602-09-5 Density 1.303 g/cm3
PSA 40.46000 LogP 5.07120
Solubility insoluble in water Melting Point 215-218 °C
Formula C20H14O2 Boiling Point 462.104 °C at 760 mmHg
Molecular Weight 286.33 Flash Point 218.932 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to beige powder
Safety 26-45-37/39-36 Risk Codes 25-36-36/37/38
Molecular Structure Molecular Structure of 602-09-5 (1,1'-Bi-2-naphthol) Hazard Symbols ToxicT, IrritantXi
Synonyms

2, 2-Dihydroxy-1,1-dinaphthyl;1,1-Bi-2-naphthol;2,2-Dihydroxybinaphthalene;2, 2-Dihydroxydinaphthyl;2,2-Dihydroxy-1,1-dinaphthyl;Bis-.beta.-naphthol;1,1-Binaphthyl-2,2-diol;[1,1'-Binaphthalene]-2,2'-diol;[1, 1-Binaphthalene]-2,2-diol;2,2-Dinaphthol;2,2-Dihydroxy-1, 1-binaphthalene;beta-Binaphthol;alpha-Binaphthyl-2,2-diol;2,2-Dihydroxydinaphthyl;Chiral binaphthol;.beta.-Binaphthol;1, 1-Bi-2-naphthol;(±)-1,1'-Bi(2-naphthol);

Article Data 129

1,1'-Bi-2-naphthol Synthetic route

135-19-3

β-naphthol

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With C24H13Cu2F9N4O7; oxygen In isopropyl alcohol at 90℃; under 760.051 Torr; for 24h;100%
With manganese (IV) dioxide In acetonitrile at 25℃; under 760.051 Torr;99.3%
With 2,6-dimethylpyridine; sodium perchlorate In acetonitrile electrolysis;98.6%
75685-01-7

2,2'-dimethoxy-1,1'-binaphthyl

A

35193-70-5

2-hydroxy-2'-methoxy-1,1'-binaphthyl

B

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With niobium pentachloride In toluene for 0.5h; Heating;A 99%
B 1%
135-19-3

β-naphthol

773-90-0, 860253-14-1

1-diazo-2(1H)naphthalenone

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With palladium diacetate In dichloromethane at 20℃; for 36h; Inert atmosphere; Schlenk technique; enantioselective reaction;98%
With iron(III) trifluoromethanesulfonate In 1,2-dichloro-ethane for 10h; Reflux; Inert atmosphere; regioselective reaction;42%
135-19-3

β-naphthol

A

633-99-8

1-chloro-2-naphthol

B

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With copper dichloride at 50 - 55℃; for 0.583333h; Neat (no solvent);A 5%
B 95%
With hydrogenchloride; iron(III) chloride

(+)-1,1'-binaphthyl-2,2'-diyl N-<(S)-α-methylbenzyl>thiophosphoroamidate

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃;
173831-50-0

rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With 1-thiopropane; zinc dibromide In dichloromethane at 20℃; for 0.116667h; Inert atmosphere;95%
121794-31-8

C38H20Cl2O4

1-(2-Carboxy-4,6-dichloro-phenyl)-naphthalene-2-carboxylic acid

B

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide In ethanolA 93%
B n/a
100465-50-7

<1,1'-Binaphthalene>-2,2'-diol dibutanoate

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 25℃; for 18h;92%
121794-33-0

C38H21NO6

1-(2-Carboxy-6-nitro-phenyl)-naphthalene-2-carboxylic acid

B

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide In ethanolA 91%
B n/a
121794-32-9

C34H17Cl2NO6

4,6-Dichloro-6'-nitro-biphenyl-2,2'-dicarboxylic acid

B

602-09-5

1,1'-bi-2-naphthol

Conditions
ConditionsYield
With potassium hydroxide In ethanolA 90%
B 88%

1,1'-Bi-2-naphthol Specification

The IUPAC name of Chiral binaphthol is 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol. With the CAS registry number 602-09-5, it is also named as 1,1'-Bi-2-naphthol. The product's categories are Intermediates of Dyes and Pigments; Naphthalene Derivatives; Aromatic Hydrocarbons (substituted) & Derivatives; API Intermediates; Miscellaneous, and the other registry number is 41024-90-2. Besides, it is white to beige powder, which should be stored in sealed, cool and dark place at 2-8 °C. In addition, its molecular formula is C20H14O2 and molecular weight is 286.33.

The other characteristics of this product can be summarized as: (1)EINECS: 210-014-0; (2)ACD/LogP: 4.86; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 4.86; (5)ACD/LogD (pH 7.4): 4.807; (6)ACD/BCF (pH 5.5): 2907.255; (7)ACD/BCF (pH 7.4): 2575.611; (8)ACD/KOC (pH 5.5): 10484.676; (9)ACD/KOC (pH 7.4): 9288.638; (10)#H bond acceptors: 2; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.758; (14)Molar Refractivity: 90.293 cm3; (15)Molar Volume: 219.809 cm3; (16)Surface Tension: 62.615 dyne/cm; (17)Density: 1.303 g/cm3; (18)Flash Point: 218.932 °C; (19)Melting Point: 215-218 °C; (20)Solubility: Dioxane: 50 mg/mL; (21)Enthalpy of Vaporization: 75.079 kJ/mol; (22)Boiling Point: 462.104 °C at 760 mmHg; (23)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Chiral binaphthol: this chemical can be prepared by coupling of 2-Naphthol with Copper(II) chloride.



You also can use iron(III) chloride as an oxidant to produce it. Additionally, this product is obtained from racemic Binol by optical resolution.

Uses of Chiral binaphthol: this chemical is often used as a ligand for transition-metal catalysed asymmetric synthesis. Similarly, it can react with Lithium aluminium hydride to get AlLibis(binaphthoxide).

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also toxic if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: c1ccc2c(c1)ccc(c2c3c4ccccc4ccc3O)O
(2)InChI: InChI=1/C20H14O2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
(3)InChIKey: PPTXVXKCQZKFBN-UHFFFAOYAX

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo oral 42mg/kg (42mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 14, Pg. 111, 1985.

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