1,1'-Bi-2-naphthol supplier

Name
1,1'-Bi-2-naphthol
EINECS 210-014-0
CAS No. 602-09-5
Article Data129
CAS DataBase
Density 1.303 g/cm³
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
Hazard Symbols T, Xi
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);
PSA 40.46000
LogP 5.07120

Synthetic route

: 135-19-3
β-naphthol

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide In ethanol	A 93% B n/a

: 100465-50-7
<1,1'-Binaphthalene>-2,2'-diol dibutanoate

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide In ethanol	A 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

Conditions	Yield
With potassium hydroxide In ethanol	A 90% B 88%

: 124040-95-5, 124098-06-2, 124098-08-4
<1,1'-Binaphthalene>-2,2'-diol butanoate

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 25℃; for 24h;	90%

: 883-99-8
3-hydroxy-2-naphthoic acid methyl ester

: 135-19-3
β-naphthol

A: 47644-69-9, 69678-00-8, 18531-91-4
dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate

B: 128702-23-8, 145415-62-9, 145415-63-0
(aS)-methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate

C: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With tert-butylamine; copper dichloride In methanol at 50℃; for 0.75h; oxidative cross-coupling;	A n/a B 87% C n/a
With tert-butylamine; copper dichloride In methanol at 50℃; for 0.5h; Yields of byproduct given;	A n/a B 86% C n/a
With tert-butylamine In methanol for 3h; Ambient temperature;	A 7 % Chromat. B 81% C 4 % Chromat.

...Expand

: 99747-67-8
2,2'-bis(benzyloxy)-1,1'-binaphthalene

A: 89867-54-9
(rac)-2′-benzyloxy-1,1′-binaphtalene-2-ol

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With niobium pentachloride In toluene at -78℃; for 3h;	A 87% B 8%

: 91-59-8
naphthalen-2-ylamine

: 135-19-3
β-naphthol

A: 194-59-2
7H-dibenzo[c,g]carbazole

B: 4488-22-6, 18531-95-8
1,1'-binaphthalene-2,2'-diamine

C: 134532-03-9, 137848-28-3, 137848-29-4
2-amino-2’-hydroxy-1,1’-binaphthyl

D: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With rac-methylbenzylamine In methanol for 48h; Ambient temperature;	A 1 % Chromat. B 2 % Chromat. C 85% D 6 % Chromat.

...Expand

: ((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexylsulfanyl)-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -20℃; for 0.5h;	85%

: 135-19-3
β-naphthol

: 99-97-8
Dimethyl-p-toluidine

A: 1346854-94-1
1-(2-(dimethylamino)-5-methylphenyl)naphthalene-2-ol

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With methanesulfonic acid; 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyaninato-iron(II) In dichloromethane at 0℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;	A 84% B 18%

...Expand

: C25H25O3PSeSi

A: 439675-12-4
bis[2-(trimethylsilyl)ethyl]-diselenide

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 0.666667h;	A 83% B n/a

: 558-30-5
2-methyl-1,2-epoxypropane

: 79082-80-7
(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol

A: 1274926-89-4
6,6'-bis(2-hydroxy-2-methylpropyl)-1,1'-binaphthyl-2,2'-diol

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
Stage #1: (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 5h; Inert atmosphere; Stage #2: 2-methyl-1,2-epoxypropane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - -40℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; pH=< 1; Cooling with ice;	A 82% B 5%

...Expand

: 701-56-4
4-methoxy-N,N-dimethylanilne

: 135-19-3
β-naphthol

A: 1346855-14-8
1-(2-(dimethylamino)-5-methoxyphenyl)naphthalene-2-ol

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With methanesulfonic acid; 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyaninato-iron(II) In dichloromethane at 0℃; for 24h; Green chemistry;	A 82% B 20%

...Expand

: 172748-15-1, 172824-34-9, 176199-86-3
7,22-dihydro-8,21-dioxa-tetranaphtho<2,1-b:1',2'-d:2'',1''-h:1''',2'''-j>cyclododecene

A: 54130-90-4, 86631-56-3, 37803-02-4
2,2'-di(bromomethyl)-1,1'-binaphthalene

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane for 1h; 0 deg C - room temperature;	A 66.6% B 81.1%
With boron tribromide In dichloromethane for 1h; 0 deg C - room temperature;	A 54.5% B 72.7%

: 573-97-7
1-bromo-2-naphthol

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With carbon dioxide; zinc; palladium on activated charcoal In water at 20℃; under 7500.6 Torr; for 48h; Ullmann coupling;	81%
With copper at 230℃;
With copper
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl-formamide 2: sulfuryl dichloride / dichloromethane 3: potassium carbonate / N,N-dimethyl-formamide 4: 1,10-Phenanthroline; potassium tert-butylate / pyridine / 4 h / 120 °C / Microwave irradiation; Inert atmosphere 5: hydrogenchloride / ethanol; water / 3 h / 50 °C View Scheme

: 883-99-8
3-hydroxy-2-naphthoic acid methyl ester

: 135-19-3
β-naphthol

A: 128702-23-8, 145415-62-9, 145415-63-0
(aS)-methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With ytterbium(III) triflate; CuCl(OH)-TMEDA In tetrahydrofuran at 20℃; for 24h; Product distribution; Further Variations:; Reagents; Solvents; Catalysts; time;	A 81% B n/a
CuCl(OH)-TMEDA In tetrahydrofuran at 20℃; for 48h;

...Expand

: 1618090-36-0
2,2′-bis(tert-butyldimethylsiloxy)-1,1′-binaphthalene

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With potassium hydrogen difluoride In methanol at 20℃; for 48h;	79%

: C35H26O2

: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78℃; for 1h;	78.7%

: 573-97-7
1-bromo-2-naphthol

: 135-19-3
β-naphthol

A: 156835-40-4
1-bromo-2'-hydroxy-2,1'-dinaphthyl ether

B: 172297-36-8
(Naphthyl-(2))-(2-hydroxy-naphthyl-(1))-aether

C: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With sodium hydroxide at 100℃; for 4h;	A n/a B n/a C 77%
With sodium hydroxide In toluene at 100℃; for 4h; Product distribution; Mechanism; var. base stoichiometry, var. solvents, var. base cation; other 2-naphthols;
With sodium hydroxide at 100℃; for 4h; Title compound not separated from byproducts;

...Expand

: 7260-11-9
phenyl 2-hydroxy-3-naphthoate

: 135-19-3
β-naphthol

A: phenyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate

B: 170889-47-1
diphenyl 2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylate

C: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With oxygen; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); copper(l) chloride In tetrahydrofuran at 20℃; for 3h;	A 72% B n/a C n/a

...Expand

: 7260-07-3
butyl 3-hydroxynaphthalene-2-carboxylate

: 135-19-3
β-naphthol

A: 145372-03-8
Butyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate

B: 145372-04-9
2,2'-Dihydroxy-[1,1']binaphthalenyl-3,3'-dicarboxylic acid dibutyl ester

C: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With tert-butylamine; copper dichloride In isopropyl alcohol at 50℃; for 2h; Yields of byproduct given;	A 71% B n/a C n/a

...Expand

: 135-19-3
β-naphthol

A: 1203550-09-7
C20H12O2

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With iron(III) chloride hexahydrate In toluene at 60℃; for 5h;	A 15% B 71%

: 3077-16-5
4-(4-methylphenyl)morpholine

: 135-19-3
β-naphthol

A: 1415461-03-8
1-(5-methyl-2-morpholinophenyl)naphthalen-2-ol

B: 602-09-5
1,1'-bi-2-naphthol

Conditions

Conditions	Yield
With methanesulfonic acid; 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyaninato-iron(II) In dichloromethane at 0℃; for 24h; Green chemistry;	A 71% B 34%

...Expand

: 602-09-5
1,1'-bi-2-naphthol

: 194-63-8
dinaphtho[2,1-b;1',2'-d]furan

Conditions

Conditions	Yield
zeolite HSZ-360 In various solvent(s) for 5h; Heating;	100%
With HY zeolite In 1,2-dichloro-benzene at 180℃; for 4h;	94%
In toluene Reflux; Acidic conditions;	94%

: 602-09-5
1,1'-bi-2-naphthol

: 79082-80-7
(S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol

Conditions

Conditions	Yield
With bromine In acetonitrile at 0℃; for 3h;	100%
With bromine In acetonitrile at 0℃; for 2.5h;	99%
With bromine at -78℃;	99.9%

: 107-30-2
chloromethyl methyl ether

: 602-09-5
1,1'-bi-2-naphthol

: 173831-50-0
rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene

Conditions

Conditions	Yield
Stage #1: 1,1'-bi-2-naphthol With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; for 4.5h;	100%
With sodium hydride In tetrahydrofuran at 20℃; for 4h;	98%
Stage #1: 1,1'-bi-2-naphthol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 0 - 20℃; for 5h; Inert atmosphere;	95%

: 358-23-6
trifluoromethylsulfonic anhydride

: 602-09-5
1,1'-bi-2-naphthol

: 141807-44-5, 126613-06-7, 128544-05-8, 128575-34-8
(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 6h;	100%
With 2,6-dimethylpyridine; dmap In dichloromethane	99%
With pyridine In dichloromethane at 20℃; for 6h;	99%

: 108-24-7
acetic anhydride

: 602-09-5
1,1'-bi-2-naphthol

: 100569-82-2, 101758-48-9, 69677-98-1
2,2'-diacetoxy-1,1'-binaphthyl

Conditions

Conditions	Yield
zeolite HSZ-360 In neat (no solvent) at 60℃; for 12h;	100%
With sodium hydroxide at 0 - 5℃; for 0.5h;	98.6%
With N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) at 80℃; for 0.25h; neat (no solvent);	97%

: 35466-83-2
allyl methyl carbonate

: 602-09-5
1,1'-bi-2-naphthol

: 59031-18-4
2,2'-bis(2-propenyloxy)-1,1'-binaphthyl

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 25℃; for 24h; Condensation;	100%

: 602-09-5
1,1'-bi-2-naphthol

: 39648-74-3, 65355-00-2, 65355-14-8
(Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol

Conditions

Conditions	Yield
With hydrogen; Ru on alumina support In ethanol at 100℃; under 37503.8 - 45004.5 Torr; for 3h; Product distribution / selectivity;	100%
With hydrogen; 5%-palladium/activated carbon In ethanol at 50 - 100℃; under 37503.8 - 60006 Torr; for 0.5 - 5.5h; Product distribution / selectivity;	98%
With hydrogen; 5%-palladium/activated carbon In ethanol at 70℃; under 37503.8 - 45004.5 Torr; Conversion of starting material;	98%
With hydrogen; Ru/C In ethanol at 50 - 70℃; under 37503.8 - 45004.5 Torr; for 0.5 - 1.5h; Product distribution / selectivity;	98%

: 602-09-5
1,1'-bi-2-naphthol

: 141807-44-5, 126613-06-7, 128544-05-8, 128575-34-8
(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

Conditions

Conditions	Yield
	100%

: 108-48-5
2,6-dimethylpyridine

: 602-09-5
1,1'-bi-2-naphthol

: 141807-44-5, 126613-06-7, 128544-05-8, 128575-34-8
(+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl

Conditions

Conditions	Yield
With dmap; trifluoromethanesulfonic acid anhydride In dichloromethane	100%
With dmap; trifluoromethanesulfonic acid anhydride In dichloromethane	100%

: 98-09-9
benzenesulfonyl chloride

: 602-09-5
1,1'-bi-2-naphthol

: 1414774-25-6, 904313-68-4, 938192-82-6
2-hydroxy-2'-phenylsulfonyloxy-1,1-binaphthyl

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	100%

: 40138-16-7
2-formylbenzene boronic acid

: 2912-98-3
(R)-1-Phenylethylhydroxylamine

: 602-09-5
1,1'-bi-2-naphthol

: C35H26BNO3

Conditions

Conditions	Yield
With magnesium sulfate; caesium carbonate In chloroform-d1 for 0.25h;	100%

...Expand

: 1726-72-3
dichloro(thiophene-2-yl)phosphine

: 602-09-5
1,1'-bi-2-naphthol

: 1470071-95-4
(1,1′-bi-2-naphthol(-2H))P(C4H3S)

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h;	100%

: 79-41-4
poly(methacrylic acid)

: 602-09-5
1,1'-bi-2-naphthol

: 159701-51-6, 96499-45-5
(±)-1,1′-binaphthyl-2-2′-diyl dimetacrylate

Conditions

Conditions	Yield
With phosphoric acid; trifluoroacetic anhydride In water at 20℃; for 0.25h;	100%

: 602-09-5
1,1'-bi-2-naphthol

: 65283-60-5
(R)-6,6'-dibromo-1,1'-binaphth-2-ol

Conditions

Conditions	Yield
With bromine In dichloromethane at -78℃;	100%

: 602-09-5
1,1'-bi-2-naphthol

: dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxathiepine 4,4-dioxide

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Sealed tube;	100%

: 602-09-5
1,1'-bi-2-naphthol

: C20H8(2)H6O2

Conditions

Conditions	Yield
With perchloric acid; chloroform-d1; d(4)-methanol at 95℃; for 96h; Inert atmosphere;	100%

: 79-08-3
bromoacetic acid

: 602-09-5
1,1'-bi-2-naphthol

: 112463-20-4, 51751-91-8, 119292-01-2
Binaphtho-2,2'-diessigsaeure

Conditions

Conditions	Yield
With potassium carbonate In methanol for 6h; Heating;	99.6%
With potassium carbonate In methanol

: 54130-90-4, 86631-56-3, 37803-02-4
2,2'-di(bromomethyl)-1,1'-binaphthalene

: 602-09-5
1,1'-bi-2-naphthol

A: 172748-15-1, 172824-34-9, 176199-86-3
7,22-dihydro-8,21-dioxa-tetranaphtho<2,1-b:1',2'-d:2'',1''-h:1''',2'''-j>cyclododecene

: C42H28O2

Conditions

Conditions	Yield
With caesium carbonate In acetone for 24h; Heating;	A 99.3% B 98.9%

...Expand

: 106-95-6
allyl bromide

: 602-09-5
1,1'-bi-2-naphthol

: 59031-18-4
2,2'-bis(2-propenyloxy)-1,1'-binaphthyl

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	99%
With potassium carbonate for 0.0666667h; Microwave irradiation;	95%
With potassium carbonate In acetone

: tris(bis(trimethylsilyl)amido)ytterbium(III)

: 602-09-5
1,1'-bi-2-naphthol

: (Li(THF)2)3Yb(1,1'-(C10H6-2-O)2)3

Conditions

Conditions	Yield
With n-BuLi In tetrahydrofuran; diethyl ether; hexane byproducts: HN(SiMe3)2; under anaerobic cond., 1 equiv. of n-BuLi in n-hexane was added to THF-soln. of naphthole-compd. at 0 °C, 1/3 equiv. of rare-earth compd.was added in Et2O to this soln., stirring at 0 °C for ca. 10 min; solvent was removed in vac., solid was recrystd. from THF-petroleum ether at -20 °C, elem. anal.;	99%

: bis(trimethylsilyl)amide yttrium(III)

: 602-09-5
1,1'-bi-2-naphthol

: (Li(THF)2)3Y(1,1'-(C10H6-2-O)2)3

Conditions

Conditions	Yield
With n-BuLi In tetrahydrofuran; diethyl ether; hexane byproducts: HN(SiMe3)2; under anaerobic cond., 1 equiv. of n-BuLi in n-hexane was added to THF-soln. of naphthole-compd. at 0 °C, 1/3 equiv. of rare-earth compd.was added in Et2O to this soln., stirring at 0 °C for ca. 10 min; solvent was removed in vac., solid was recrystd. from THF-petroleum ether at -20 °C;	99%
With n-BuLi In tetrahydrofuran; diethyl ether; hexane byproducts: HN(SiMe3)2; under anaerobic cond., 1 equiv. of n-BuLi in n-hexane was added to THF-soln. of naphthole-compd. at 0 °C, 1/3 equiv. of rare-earth compd.was added in Et2O to this soln., stirring at 0 °C for ca. 10 min; solvent was removed in vac., solid was recrystd. from THF-petroleum ether at -20 °C, elem. anal.;	99%

: tris(bis(trimethylsilyl)amido)europium(III)

: 602-09-5
1,1'-bi-2-naphthol

: (Li(THF)2)3Eu(1,1'-(C10H6-2-O)2)3

Conditions

Conditions	Yield
With t-BuLi In tetrahydrofuran; diethyl ether; hexane byproducts: HN(SiMe3)2; under anaerobic cond., 1 equiv. of t-BuLi in hexane was added to THF-soln. of naphthole-compd. at 0 °C, 1/3 equiv. rare-earth compd. was added in Et2O to this soln., stirring at 0 °C for ca. 10 min; solvent was removed in vac., solid was recrystd. from THF-petroleum ether at -20 °C;	99%

: tris(bis(trimethylsilyl)amido)praseodymium(III)

: 602-09-5
1,1'-bi-2-naphthol

: (Li(THF)2)3Pr(1,1'-(C10H6-2-O)2)3

Conditions

Conditions	Yield
With n-BuLi In tetrahydrofuran; diethyl ether; hexane byproducts: HN(SiMe3)2; under anaerobic cond., 1 equiv. of n-BuLi in n-hexane was added to THF-soln. of naphthole-compd. at 0 °C, 1/3 equiv. of rare-earth compd.was added in Et2O to this soln., stirring at 0 °C for ca. 10 min; solvent was removed in vac., solid was recrystd. from THF-petroleum ether at -20 °C, elem. anal.;	99%

: 66003-76-7
Diphenyliodonium triflate

: 602-09-5
1,1'-bi-2-naphthol

: 2,2'-diphenoxy-1,1'-binaphthalene

Conditions

Conditions	Yield
Stage #1: 1,1'-bi-2-naphthol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: Diphenyliodonium triflate In tetrahydrofuran at 40℃; for 0.75h;	99%
Stage #1: 1,1'-bi-2-naphthol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: Diphenyliodonium triflate In tetrahydrofuran at 40℃; for 0.75h;	99%
With sodium hydroxide In water at 20 - 50℃; for 17.5h;	98%

: 602-09-5
1,1'-bi-2-naphthol

: 1326309-92-5, 1334180-26-5, 236401-85-7
1,1'-binaphthyl-2,2'-diyl sulfite

Conditions

Conditions	Yield
With thionyl chloride; triethylamine In diethyl ether at 0℃;	99%
With pyridine; thionyl chloride In diethyl ether at 0℃; for 3h; Inert atmosphere;	99%

: 65-85-0
benzoic acid

: 602-09-5
1,1'-bi-2-naphthol

: 53545-44-1
(±)-1,1′-binaphthyl-2-2′-diyl dibenzoate

Conditions

Conditions	Yield
With phosphoric acid; trifluoroacetic anhydride In water at 20℃; for 0.25h;	99%

: Diphenyliodonium fluoride

: 602-09-5
1,1'-bi-2-naphthol

: 2,2'-diphenoxy-1,1'-binaphthalene

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 40℃;	99%

: 542-69-8
1-iodo-butane

: 201230-82-2
carbon monoxide

: 602-09-5
1,1'-bi-2-naphthol

: 100465-51-8, 110902-38-0
<1,1'-Binaphthalene>-2,2'-diol dipentanoate

Conditions

Conditions	Yield
With rhodium(III) chloride; 1,3-bis-(diphenylphosphino)propane; sodium carbonate; sodium bromide In 1,4-dioxane at 120℃; under 750.075 Torr; for 24h; Inert atmosphere; chemoselective reaction;	99%

...Expand

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.

Product Name

1,1'-Bi-2-naphthol

Synthetic route

1,1'-Bi-2-naphthol Specification

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