Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water at 24℃; for 16h; Inert atmosphere; | A n/a B 98% |
1,1'-bi-2-naphthol
(R)-1,1'-Bi-2-naphthol
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
1,1'-bi-2-naphthol
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
In ethyl acetate for 2h; Reflux; Resolution of racemate; Green chemistry; | A n/a B 96% |
1,1'-bi-2-naphthol
(R)-1,1'-Bi-2-naphthol
(S)-[1,1']-binaphthalenyl-2,2'-diol
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
(R)-1,1'-Bi-2-naphthol
(S)-[1,1']-binaphthalenyl-2,2'-diol
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; |
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With boron trichloride In n-heptane; dichloromethane at 25℃; for 24h; Inert atmosphere; | A 76% B 85% |
β-naphthol
(R)-1,1'-Bi-2-naphthol
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 |
phenylmagnesium bromide
(R)-1,1'-Bi-2-naphthol
B
(-)-(S)-tert-butyl phenyl sulfoxide
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)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; methanol at 20℃; | 84% |
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 0.166667h; Inert atmosphere; | 83% |
With methanol; potassium carbonate |
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -78℃; | 80% |
[1,1']Binaphthalenyl-2,2'-diol; compound with 1-((R)-methanesulfinyl)-3-methyl-benzene
(R)-1,1'-Bi-2-naphthol
B
(R)-1-methyl-3-(methylsulfinyl)benzene
Conditions | Yield |
---|---|
In benzene | A 77% B 77% |
Conditions | Yield |
---|---|
In acetonitrile for 3h; Reflux; | A 76% B 38% |
C34H18N2O8
(R)-1,1'-Bi-2-naphthol
6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol | A 73% B 65% |
(+/-)-1,1'-Binaphthyl-2,2'-diyl phosphorochloridate
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 73% |
4-methoxyphenyl magnesium bromide
(R)-1,1'-Bi-2-naphthol
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% |
1-naphthylmagnesiumbromide
(R)-1,1'-Bi-2-naphthol
B
(S)-1-<(2-Methylprop-2-yl)sulfinyl>naphthalene
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)-1,1'-Bi-2-naphthol
B
(4aS,9S,10aS)-1,2,3,4,4a,9,10,10a-Octahydro-6-methoxy-1,1,4a-trimethylphenanthrene-9-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 24h; Hydrolysis; Heating; | A n/a B 67% |
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With hydrogenchloride | 60% |
β-naphthol
A
1-chloro-2-naphthol
(R)-1,1'-Bi-2-naphthol
(S)-[1,1']-binaphthalenyl-2,2'-diol
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
(R)-6,6'-dibromo-1,1'-binaphth-2-ol
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
methyl iodide
(R)-2,2'-dimethoxy-1,1'-dinaphthyl
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% |
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
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
chloromethyl methyl ether
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
(R)-1,1'-Bi-2-naphthol
(R)-(-)-1,1'-bi-2-naphthol triflate
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
(Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol
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
(R)-1,1'-Bi-2-naphthol
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
N,N,N',N'-Tetramethylphosphorodiamidic chloride
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 100% |
With sodium hydride In tetrahydrofuran at 0℃; for 3h; | 99% |
methyl 3-hydroxybenzoate
(R)-1,1'-Bi-2-naphthol
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
(R)-1-Phenylethylhydroxylamine
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With magnesium sulfate; caesium carbonate In chloroform-d1 at 20℃; for 0.25h; | 100% |
(R)-1,1'-Bi-2-naphthol
2-naphthylacetic acid
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
allyl bromide
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
benzoic acid
Conditions | Yield |
---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 15h; Esterification; | 99% |
(2-trimethylethylsilylethoxy)methyl chloride
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 2h; | 99% |
(R)-1,1'-Bi-2-naphthol
C18H34N3P
Conditions | Yield |
---|---|
In toluene at 80℃; for 2h; | 99% |
(R)-1,1'-Bi-2-naphthol
Diphenylphosphinic chloride
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
diethyl chlorophosphate
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
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine In diethyl ether at 0℃; | 99% |
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% |
(R)-1,1'-Bi-2-naphthol
dimethylaluminum chloride
Conditions | Yield |
---|---|
In dichloromethane at -15℃; for 1h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; | 99% |
(R)-1,1'-Bi-2-naphthol
8-tosyloxy-3,6-dioxaoctanol
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 24h; Heating; | 98.4% |
(R)-1,1'-Bi-2-naphthol
(R)-(-)-4-mercapto-4-sulfide-dinaphtho<2,1-d:1',2'-f><1,3,2>dioxaphosphepin
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; |
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
Isopropyl isocyanate
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran; dichloromethane at 60℃; for 48h; | 98% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
2-formylbenzene boronic acid
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
In chloroform at 20℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 98% |
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 |
(R)-(+)-1,1'-Bi-2-naphthol with cas registry number of 18531-94-7 is white to light yellow crystal powder, also called beta-Binaphthol; 1,1'-Bi-2-naphthol; Chiral binaphthol; Bis-beta-naphtho ; 2,2'-Dinaphthol; .beta.-Binaphthol; 1,1'-Bis-2-naphthol; 2,2'-Dihydroxydinaphthyl; Bis-.beta.-naphthol; 2,2'-Dihydroxybinaphthalene. It is an organic compound that is often used as a ligand for transition-metal catalysed asymmetric synthesis.
Physical properties about (R)-(+)-1,1'-Bi-2-naphthol are: (1)ACD/LogP: 4.861; (2)ACD/LogD (pH 5.5): 4.86; (3)ACD/LogD (pH 7.4): 4.81; (4)ACD/BCF (pH 5.5): 2907.26; (5)ACD/BCF (pH 7.4): 2575.61; (6)ACD/KOC (pH 5.5): 10484.68; (7)ACD/KOC (pH 7.4): 9288.64; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.758 ; (12)Molar Refractivity: 90.293 cm3; (13)Molar Volume: 219.809 cm3; (14)Polarizability: 35.795 10-24cm3; (15)Surface Tension: 62.6150016784668 dyne/cm; (16)Density: 1.303 g/cm3; (17)Flash Point: 218.932 °C; (18)Enthalpy of Vaporization: 75.079 kJ/mol; (19)Boiling Point: 462.104 °C at 760 mmHg;
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Avoid contact with skin and eyes;
4. Wear suitable protective clothing;
You can still convert the following datas into molecular structure:
(1)SMILES:c1ccc2c(c1)ccc(c2c3c4ccccc4ccc3O)O;
(2)Std. InChI:InChI=1S/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)Std. InChIKey:PPTXVXKCQZKFBN-UHFFFAOYSA-N
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