18531-94-7

Basic information

• Product Name: (R)-(+)-1,1'-Bi-2-naphthol
• Synonyms: (R)-(+)-1,1'-BIS(2-NAPHTHOL);(R)-(+)-1,1'-BINAPHTHYL-2,2'-DIOL;(R)-[1,1]-BINAPHTHALENYL-2,2'-DIOL;R(+)-1,1'-BINAPHTHALENE-2,2'-DIOL;(R)-(+)-1,1'-BI(2,2'-NAPHTHOL);(R)-(+)-1,1'-BI-2-NAPHTHOL;(R)-(+)-1,1-BI-2-NAPHTHOL;(R)-1,1'-BI-2-NAPHTHOL
• CAS NO: 18531-94-7
• Molecular Formula: C₂₀H₁₄O₂
• Molecular Weight: 286.32
• EINECS: 210-014-0
• Product Categories: Intermediates of Dyes and Pigments;Alcohols and Derivatives;chiral;CHIRAL COMPOUNDS;Chiral Reagent;Asymmetric Synthesis;Synthetic Organic Chemistry;Chiral Compound;Peptide;BINOL Series;Chiral Oxygen
• Mol File: 18531-94-7.mol
• Article Data: 150

Chemical Properties

• Melting Point: 215-218 °C
• Boiling Point: 388.69°C (rough estimate)
• Appearance: white to off-white/Powder
• Density: 1.301
• Refractive Index: 36.0 ° (C=1, THF)
• Storage Temp.: 2-8°C
• Solubility: dioxane: 50 mg/mL, clear
• PKA: 8.29±0.50(Predicted)
• Water Solubility: Insoluble in water. Solubility in THF within almost transparency). Soluble in dioxane 50 mg/mL.
• Merck: 14,1226
• BRN: 3616837
• CAS DataBase Reference: (R)-(+)-1,1'-Bi-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,1'-Bi-2-naphthol(18531-94-7)
• EPA Substance Registry System: (R)-(+)-1,1'-Bi-2-naphthol(18531-94-7)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36-36/37/38
• Safety Statements: 26-45-24/25-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DU3106100
• F: 10
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 18531-94-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-1,1'-Bi-2-naphthol is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of enantiomerically pure drugs, which is crucial in the development of more effective and safer medications.
Used in Chemical Industry:
(R)-(+)-1,1'-Bi-2-naphthol is used as a chiral binapthol imminium salt precursor for an asymmetric epoxidation of olefins. This process is essential in the synthesis of various chiral compounds, which are widely used in the chemical industry for the production of specialty chemicals, agrochemicals, and other industrial products.
Used in Research and Development:
(R)-(+)-1,1'-Bi-2-naphthol is used as a research compound in the development of new methods and techniques for asymmetric synthesis. Its unique properties make it an ideal candidate for studying the effects of chirality on chemical reactions and the development of novel catalysts and reagents for enantioselective transformations.

Purification Methods

Dissolve it in cold 2.5N NaOH, extract with CH2Cl2, and acidify with 5% HCl. Collect the white precipitate and recrystallise it from aqueous EtOH and dry it in a vacuum [Akimoto & Yamada Tetrahedron 27 5999 1971]. It is optically stable in dioxane-water (100o/24hours). Racemisation: 72% in 1.2N HCl at 100o/24hours and 68% in 0.67M KOH in BuOH at 118o/23hours [Kyba et al. J Am Chem Soc 95 2693 1973]. It has also been crystallised from *C6H6 (solubility is 1%) using Norite or aqueous EtOH after chromatography through silica gel, eluting with Me2CO/*C6H6. [Kyba et al. J Org Chem 42 4173 1977; see also Brussee & Jansen Tetrahedron Lett 24 3261 1983, Akimoto & Yamada Tetrahedron 27 5999 1971, Beilstein 6 IV 7020.]

Synthetic route

C25H22O3 → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 24℃; for 16h; Inert atmosphere;	A n/a B 98%

1,1'-bi-2-naphthol (602-09-5) → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
Stage #1: 1,1'-bi-2-naphthol With copper(l) chloride; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine In methanol; dichloromethane at -20 - 20℃; for 24h; Inert atmosphere; Darkness; Stage #2: With sodium hydrogencarbonate In methanol; dichloromethane; water at -20℃; optical yield given as %ee; enantioselective reaction;	96%
Multistep reaction;	86%
Stage #1: 1,1'-bi-2-naphthol With (3R)-3-propyl-4-((S)-1'-phenylethylamino)butanoic acid; (3S)-3-propyl-4-((S)-1'-phenylethylamino)butanoic acid In methanol at 60℃; for 1h; Resolution of racemate; Stage #2: With (3R)-3-propyl-4-((R)-1'-phenylethylamino)butanoic acid; (3S)-3-propyl-4-((R)-1'-phenylethylamino)butanoic acid In methanol at 60℃; for 1h; Resolution of racemate; Stage #3: With hydrogenchloride In water; ethyl acetate	68%

(5aS,10aS)-octahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione (6708-06-1, 19943-27-2, 20873-90-9, 36588-47-3, 36588-48-4, 53990-71-9, 53990-72-0) + 1,1'-bi-2-naphthol (602-09-5) → C20H14O2*C10H14N2O2 + (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
In ethyl acetate for 2h; Reflux; Resolution of racemate; Green chemistry;	A n/a B 96%

1,1'-bi-2-naphthol (602-09-5) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Conditions	Yield
With N-benzylcinchoninium chloride In acetonitrile for 4h; resolution of racemate; Heating;	A 95% B 95%
With (-)-N-benzylcinchonidinium chloride In acetonitrile for 4h; Heating;	A 83% B n/a
Stage #1: 1,1'-bi-2-naphthol With dimethylsulfide borane complex In tetrahydrofuran; toluene at 80℃; for 0.5h; Inert atmosphere; Stage #2: With Quinine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 20℃; for 0.5h; Inert atmosphere;	A n/a B 46%

β-naphthol (135-19-3) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Conditions	Yield
With oxygen; oxovanadium(IV) In tetrachloromethane at 20℃; for 144h;	A 94% B n/a
With dexamfetamine; copper dichloride In methanol Product distribution; Mechanism; stereoselectivity of the coupling reaction with various optically active amines; variation of the temperature;
With dexamfetamine; copper dichloride In methanol at 25℃; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

N-(2-((2'-hydroxy-[1,1'-binaphthalen]-2-yl)oxy)octyl)-3,5-dinitrobenzamide → N-(2-chlorooctyl)-3,5-dinitrobenzamide + (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With boron trichloride In n-heptane; dichloromethane at 25℃; for 24h; Inert atmosphere;	A 76% B 85%

β-naphthol (135-19-3) → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With oxygen; C26H28N2O9V2 In tetrachloromethane at 0℃; for 168 - 192h; Product distribution / selectivity;	84%
With C34H36N2O10V2 In dichloromethane at 30℃; for 24h; enantioselective reaction;	100 %Spectr.
Multi-step reaction with 3 steps 1: iron(III) chloride / water / Reflux 2: triethylamine; dmap / dichloromethane / 24 h / 20 °C / Inert atmosphere; Resolution of racemate 3: potassium hydroxide / methanol; 1,4-dioxane / 20 °C View Scheme

(R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate) + phenylmagnesium bromide (100-58-3) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (-)-(S)-tert-butyl phenyl sulfoxide (4850-72-0)

Conditions	Yield
Stage #1: (R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate); phenylmagnesium bromide In tetrahydrofuran at -78 - -20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran at -20 - 20℃; Inert atmosphere; optical yield given as %ee;	A n/a B 84%

(R)-2'-hydroxy-[1,1'-binaphthalen]-2-yl (1R,4S)-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-1-carboxylate → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; methanol at 20℃;	84%

(R)-(+)-1-(2-hydroxynapthalen-1-yl)napthalen-2-yl acetate → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 0.166667h; Inert atmosphere;	83%
With methanol; potassium carbonate

C26H24O5 → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With boron tribromide In dichloromethane at -78℃;	80%

[1,1']Binaphthalenyl-2,2'-diol; compound with 1-((R)-methanesulfinyl)-3-methyl-benzene (96026-44-7) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (R)-1-methyl-3-(methylsulfinyl)benzene (84413-69-4)

Conditions	Yield
In benzene	A 77% B 77%

L-proline (147-85-3) + 1,1'-bi-2-naphthol (602-09-5) → (S)-proline (S)-1,1'-bi-2-naphthol 1:2 complex + (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
In acetonitrile for 3h; Reflux;	A 76% B 38%

C34H18N2O8 (93274-50-1) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid (5457-32-9, 50573-78-9)

Conditions	Yield
With potassium hydroxide In ethanol	A 73% B 65%

(+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate (124583-86-4, 124583-87-5, 124648-60-8) → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With lithium aluminium tetrahydride	73%

(R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate) + 4-methoxyphenyl magnesium bromide (13139-86-1) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (-)-(S)-tert-butyl (4-methoxyphenyl) sulfoxide

Conditions	Yield
Stage #1: (R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate); 4-methoxyphenyl magnesium bromide In tetrahydrofuran at -78 - -20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran at -20 - 20℃; Inert atmosphere; optical yield given as %ee;	A n/a B 73%

(R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate) + 1-naphthylmagnesiumbromide (703-55-9) → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-1-<(2-Methylprop-2-yl)sulfinyl>naphthalene (203503-64-4)

Conditions	Yield
Stage #1: (R,S(S),S(S))-1,1'-binaphthalene-2,2'-diyl bis-(tert-butylsulfinate); 1-naphthylmagnesiumbromide In tetrahydrofuran at -78 - -20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran at -20 - 20℃; Inert atmosphere; optical yield given as %ee;	A n/a B 71%

(R)-(+)-2'-Hydroxy-1,1'-binaphthyl-2-yl (4aS,9R,10aS)-1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,1,4a-trimethylphenanthrene-9-carboxylate → (R)-1,1'-Bi-2-naphthol (18531-94-7) + (4aS,9S,10aS)-1,2,3,4,4a,9,10,10a-Octahydro-6-methoxy-1,1,4a-trimethylphenanthrene-9-carboxylic acid (303962-65-4)

Conditions	Yield
With potassium hydroxide In ethanol for 24h; Hydrolysis; Heating;	A n/a B 67%

C26H29N2O(1+)*C20H14O2*Cl(1-) → (R)-1,1'-Bi-2-naphthol (18531-94-7)

Conditions	Yield
With hydrogenchloride	60%

β-naphthol (135-19-3) → 1-chloro-2-naphthol (633-99-8) + (R)-1,1'-Bi-2-naphthol (18531-94-7) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2)

Conditions	Yield
With L-proline; copper dichloride at 60℃; for 0.5h; Neat (no solvent); optical yield given as %ee; enantioselective reaction;	A 60% B n/a C n/a

(R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-6,6'-dibromo-1,1'-binaphth-2-ol (65283-60-5)

Conditions	Yield
With bromine In dichloromethane at -78℃; Inert atmosphere;	100%
With bromine at -78℃;	99.9%
With bromine In dichloromethane at -75 - 20℃; for 3h;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + methyl iodide (74-88-4) → (R)-2,2'-dimethoxy-1,1'-dinaphthyl (35294-28-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	100%
With potassium carbonate In acetone Reflux;	100%
With potassium carbonate In acetone for 20h; Schlenk technique; Inert atmosphere; Reflux;	100%

ethyl bromide (74-96-4) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-(+)-2,2'-diethoxy-1,1'-binaphthalene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 24h;	100%
With caesium carbonate In acetone at 25℃; for 3h;	99%
With potassium carbonate; sodium iodide	98%
With potassium carbonate In acetonitrile Reflux;	98%
With potassium carbonate In acetone at 90℃; for 24h;

(R)-1,1'-Bi-2-naphthol (18531-94-7) → [(R)-1,1'-binaphthyl-2,2'-diyl]chlorophosphite

Conditions	Yield
With triethylamine; phosphorus trichloride In tetrahydrofuran at 0℃; for 6h;	100%
With phosphorus trichloride for 16h; Inert atmosphere; Reflux;	100%
With phosphorus trichloride Reflux; Inert atmosphere;	100%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + chloromethyl methyl ether (107-30-2) → (Ra)-2,2'-bis(methoxy-methyloxy)-1,1'-binaphthalene

Conditions	Yield
Stage #1: (R)-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%
Stage #1: (R)-1,1'-Bi-2-naphthol With sodium hydride In tetrahydrofuran at 0 - 20℃; activation; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; for 4.5h; Condensation; Further stages.;	100%
Stage #1: (R)-1,1'-Bi-2-naphthol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 20h; Metallation; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 20℃; for 1h; Etherification; Further stages.;	100%

trifluoromethylsulfonic anhydride (358-23-6) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-(-)-1,1'-bi-2-naphthol triflate (128544-05-8, 128575-34-8, 141807-44-5, 126613-06-7)

Conditions	Yield
With 2,6-dimethylpyridine	100%
With pyridine Inert atmosphere;	100%
With pyridine In dichloromethane at 20℃; for 5h; Inert atmosphere;	100%

(R)-1,1'-Bi-2-naphthol (18531-94-7) → (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol (39648-74-3, 65355-00-2, 65355-14-8)

Conditions	Yield
With hydrogen; aluminum oxide; ruthenium In ethanol at 100℃; under 37503 - 45003.6 Torr; for 4h;	100%
With hydrogen; platinum(IV) oxide In acetic acid at 20℃; under 5168.35 Torr; for 72h;	100%
With palladium 10% on activated carbon; hydrogen In ethanol at 70℃; under 37503.8 Torr; for 16h; Autoclave;	100%

4-bromoethylbutanoate (2969-81-5) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-2,2'-bis(3-carboxypropoxy)-1,1-binaphthyl diethyl ester

Conditions	Yield
With potassium carbonate In acetone for 48h; Heating;	100%
With potassium carbonate In acetone for 96h; Heating / reflux;	68%
With potassium carbonate In acetone for 24h; Reflux;

(R)-1,1'-Bi-2-naphthol (18531-94-7) + N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8) → C28H36N4O4P2

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	100%
With sodium hydride In tetrahydrofuran at 0℃; for 3h;	99%

methyl 3-hydroxybenzoate (19438-10-9) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (-)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-3-oxybenzoic acid methyl ester

Conditions	Yield
Stage #1: (R)-1,1'-Bi-2-naphthol With triethylamine; phosphorus trichloride In tetrahydrofuran at -3 - 20℃; Stage #2: methyl 3-hydroxybenzoate With triethylamine In tetrahydrofuran at 20℃; for 24h; Further stages.;	100%

2-formylbenzene boronic acid (40138-16-7) + (R)-1-Phenylethylhydroxylamine (2912-98-3) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → C35H26BNO3

Conditions	Yield
With magnesium sulfate; caesium carbonate In chloroform-d1 at 20℃; for 0.25h;	100%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + 2-naphthylacetic acid (581-96-4) → Naphthalen-2-yl-acetic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h; Ambient temperature;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + allyl bromide (106-95-6) → (R)-(+)-2,2'-bis(2-propen-1-yloxy)-1,1'-dinaphthyl

Conditions	Yield
With potassium carbonate In acetone for 70h; Heating;	99%
With potassium carbonate In acetone for 2h; Heating;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + benzoic acid (65-85-0) → (R)-2'-hydroxy-1,1'-binaphthalene-2-yl benzoate

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 15h; Esterification;	99%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-2,2'-Bis[2-(trimethylsilyl)ethoxymethoxy]-1,1'-binaphthyl

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2h;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + C18H34N3P (615257-62-0) → {1-[2-(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-phenyl]-ethyl}-dimethyl-amine

Conditions	Yield
In toluene at 80℃; for 2h;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + Diphenylphosphinic chloride (1499-21-4) → (Ra)-1,1'-binaphthalene-2,2'-bis(diphenylphosphinate)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 3h;	99%
Stage #1: (R)-1,1'-Bi-2-naphthol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: Diphenylphosphinic chloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.25h; Inert atmosphere;	96%
Stage #1: (R)-1,1'-Bi-2-naphthol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: Diphenylphosphinic chloride In tetrahydrofuran at 0 - 20℃;
With sodium hydride In tetrahydrofuran at 0 - 20℃;

(R)-1,1'-Bi-2-naphthol (18531-94-7) + diethyl chlorophosphate (814-49-3) → (R)-[1,1′-binaphthalene]-2,2′-diyl tetraethyl bis(phosphate)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 3h;	99%
With sodium hydride In tetrahydrofuran at 0 - 20℃;

(R)-1,1'-Bi-2-naphthol (18531-94-7) → 1,1'-binaphthyl-2,2'-diyl sulfite

Conditions	Yield
With thionyl chloride; triethylamine In diethyl ether at 0℃;	99%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → C29H22NO2P

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydroisoquinoline With triethylamine; phosphorus trichloride In toluene at 0 - 80℃; Inert atmosphere; Stage #2: (R)-1,1'-Bi-2-naphthol With triethylamine In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere;	99%

1-[(1′S,2′R,5′S)-(+)-menthoxymethyl]-3-methylimidazolium bis(trifluoromethylsulfonyl)imide + (R)-1,1'-Bi-2-naphthol (18531-94-7) + dimethylaluminum chloride (1184-58-3) → C23H15AlF6NO6S2(1-)*C15H27N2O(1+)

Conditions	Yield
In dichloromethane at -15℃; for 1h; Inert atmosphere;	99%

C14H19BrO3 + (R)-1,1'-Bi-2-naphthol (18531-94-7) → C48H50O8

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere;	99%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + 8-tosyloxy-3,6-dioxaoctanol (77544-68-4) → (R)-2,2'-bis(8-hydroxy-3,6-dioxa-1-octyloxy)-1,1'-binaphthyl

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Heating;	98.4%

(R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-(-)-4-mercapto-4-sulfide-dinaphtho<2,1-d:1',2'-f><1,3,2>dioxaphosphepin (70101-69-8, 70144-34-2, 70144-35-3)

Conditions	Yield
With tetraphosphorus decasulfide In m-xylene at 20℃; for 50h; Inert atmosphere; Reflux;	98%
With tetraphosphorus decasulfide In xylene 1.) reflux, 0.5 h, 2.) room temperature, 48 h;	70%
With diphosphorus pentasulfide In toluene for 24h; Heating;
With diphosphorus pentasulfide In toluene at 110℃; for 24h; Inert atmosphere;

1-bromo-hexane (111-25-1) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (R)-2,2'-dihexyloxybi-1,1'-naphthalene

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	98%
With sodium hydroxide In water; acetone for 18h; Heating;	95.6%
With potassium carbonate In acetonitrile for 16h; Heating;	95%

(R)-1,1'-Bi-2-naphthol (18531-94-7) + Isopropyl isocyanate (1795-48-8) → (R)-O,O'-[1,1']-binaphthyl-2,2'-diyl di(N-isopropylcarbamate)

Conditions	Yield
With dmap In tetrahydrofuran; dichloromethane at 60℃; for 48h;	98%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + 2-formylbenzene boronic acid (40138-16-7) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → (4S,5S)-2-(2-((Ra)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin-4-yl)phenyl)-4,5-diphenylimidazolidine

Conditions	Yield
In chloroform at 20℃; for 1h;	98%

trifluoromethane sulfonyl chloride (421-83-0) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → C22H12F6O2

Conditions	Yield
With pyridine In dichloromethane	98%

Pyrene-1-carboxylic acid (19694-02-1) + (R)-1,1'-Bi-2-naphthol (18531-94-7) → C54H30O4

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;	98%
With 4-methyl-N-methylpyridinium p-toluenesulfonate salt; diisopropyl-carbodiimide In dichloromethane

Upstream product

• 108-05-4 vinyl acetate 
• 602-09-5 1,1'-bi-2-naphthol 
• 123-20-6 vinyl n-butyrate 
• 3050-69-9 vinyl caproate 
• 818-44-0 vinyl octanoate 
• 79044-35-2 2-(2-propenyloxy)-7-hydroxynaphthalene 
• 124040-95-5 <1,1'-Binaphthalene>-2,2'-diol butanoate 
• 180581-29-7 4-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 124583-86-4 (+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate 
• 135-19-3 β-naphthol 

Downstream Products

• 422509-53-3 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-(1-phenyl-ethyl)-amine 
• 124931-81-3 (R_a)-phenylacetic acid 2'-hydroxy[1,1']binaphthalenyl-2-ester 
• 444667-33-8 4-((R,R)-2,5-diphenylpyrrolidine)-(R)-dinaphthdioxaphosphepin 
• 391860-55-2 (11bR, 11'bR)-4,4'-(oxydi-2,1-phenylene)bis-dinaphtho[2,1-d:,1',2'-f][1,3,2]dioxaphosphepin 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 137156-22-0 binaphthol chlorophosphite 

Relevant articles and documents

An improved approach to (R)-(+)-1,1'-bi-2-naphthol of 100% enantiomeric excess via a cyclic borate ester

The preparation for (R)-(+)-1,1'-bi-2-naphthol of 100% ee using cinchonine as a resolving agent via a cyclic borate ester is described.

Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved Materials

Racemic 2,2'-dihydroxy-1,1'-binaphyl and 10,10'-dihydroxy-9,9'-biphenanthryl have been resolved effectively by crystalline complexation with commercially available N-alkylcinchonidium halides.The resolved complexes were studied by X-ray diffraction methods in order to characterize the intermolecular interaction and recognition schemes.The results indicate the significance of directional hydrogen bonding and aryl-aryl interaction modes in the molecular recognition process.

Chiral dinuclear vanadium(v) catalysts for oxidative coupling of 2-naphthols

Preparation and structural analysis of chiral dinuclear vanadium(v) catalysts with high catalytic activity for the oxidative coupling of 2-naphthols are described. The Royal Society of Chemistry.

A new method for the synthesis of H4-BINOL

(Chemical Equation Presented) A method amenable to the gram scale synthesis of (R)-H4-BINOL, a derivative of (R)-BINOL and ligand of interest in asymmetric catalysis, is described. The key step is the net partial hydrogenation of (R)-BINOL made possible by prior bis-etherification of the parent BINOL.

Dual activation in oxidative coupling of 2-naphthols catalyzed by chiral dinuclear vanadium complexes

An efficient enantioselective oxidative coupling of 2-naphthol derivatives based on a concept of dual activation catalysis is realized. A chiral dinuclear vanadium(IV) complex (Ra,S,S)-1e possessing (S)-tert-leucine moieties at the 3,3′-positions of the (R)-binaphthyl skeleton was developed, which was found to promote the oxidative coupling of 2-naphthol to afford (S)-BINOL with 91% ee. To verify the dual activation mechanism, mononuclear vanadium(IV) complex (S)-8 was also prepared. Kinetic analysis revealed that the reaction rate of oxidative coupling of 2-naphthol promoted by (Ra,S,S)-1e is 48.3 times faster than that of (S)-8. The two vanadium metals in the chiral complex activate two molecules of 2-naphthol simultaneously in an intramolecular manner coupling reaction, achieving a high reaction rate with high enantiocontrol. Reaction mechanisms of the oxidative coupling reaction promoted by either vanadium(IV) or vanadium(V) complexes are also described.

Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by Camellia sinensis cell culture

Optically active 1,1′-binaphthyl-2,2′-diols were synthesized by oxidative coupling of 2-naphthols using Camellia sinensis cell culture as a catalytic system.

Irreversible visual sensing of humidity using a cholesteric liquid crystal

Irreversible optical sensing of humidity by a doped cholesteric liquid crystal is achieved by using a thin film of nematic host E7 with a binaphthylorthosilicate ester as dopant (guest). The film changes its color from blue (to green to orange to red) to colorless when exposed to humidity as the dopant is hydrolyzed. The Royal Society of Chemistry 2012.

A new and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diol: Resolution of racemic [1,1′-binaphthalene]-2,2′-diol with threo-(1s,2s)-2-amino-1-(4-nitrophenyl)propane-1,3-diol-cyclohexanone condensate

An economic and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diols is reported. Thus, a condensate of threo-(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol and cyclohexanone (CHANP) was used as a resolving agent. A 2:1:1 mixture of racemic [1,1′-binaphthalene]-2,2′-diol, boric acid, and CHANP was refluxed for several hours in THF or MeCN to give a white precipitate of bis((R)-[1,1′-binaphthalene]-2,2′-diol}boric acid CHANP derivative, from the precipitate, and a filtrate separated from the precipitate, (R)- and (S)-[1,1′-binaphthalene]-2,2′-diol of 100% ee were obtained in ca. 65% yield, respectively.

Lipase-catalyzed stereoselective resolution and desymmetrization of binaphthols

We have investigated the use of lipoprotein lipase enzymes from Pseudomonas sp. and Pseudomonas fluorescens for the enantioselective resolution and desymmetrization of racemic binaphthols. The reactions were carried out using a non-aqueous environment (iPr2O/acetone/vinyl acetate), and yielded mono-acetate ester products of the parent unsubstituted substrate, the 6,6′-dibromo-substrate, and the 6,6′-dimethoxy-substrate with high enantiomeric selectivity.

The rational design of novel chiral oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols

Several novel chiral oxovanadium(IV) complexes have been designed and prepared for the asymmetric catalytic oxidative coupling of 2-naphthols with high enantioselectivities of 83-98% ee.