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(R)-(+)-1,1'-Bi-2-naphthol
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  • Name (R)-(+)-1,1'-Bi-2-naphthol
  • EINECS210-014-0
  • CAS No. 18531-94-7
  • Density1.301 g/cm3
  • PSA40.46000
  • LogP5.07120
  • SolubilityDioxane: 50 mg/mL, clear
  • Melting Point215-218 °C
  • FormulaC20H14O2
  • Boiling Point388.69°C (rough estimate)
  • Molecular Weight286.33
  • Flash PointN/A
  • Transport InformationUN 2811 6.1/PG 3
  • Appearancewhite to light yellow crystal powder
  • Safety26-45-24/25-36
  • Risk Codes25-36-36/37/38
  • Molecular Structure
    Molecular Structure of 18531-94-7 ((R)-(+)-1,1'-Bi-2-naphthol)
  • Hazard SymbolsToxicT,IrritantXi
  • SynonymsToxicT,IrritantXi
  • Article Data152

(R)-(+)-1,1'-Bi-2-naphthol Synthetic route

C25H22O3

18531-94-7

(R)-1,1'-Bi-2-naphthol

18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 24℃; for 16h; Inert atmosphere;A n/a
B 98%
602-09-5

1,1'-bi-2-naphthol

18531-94-7

(R)-1,1'-Bi-2-naphthol

Conditions
ConditionsYield
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%
6708-06-1, 19943-27-2, 20873-90-9, 36588-47-3, 36588-48-4, 53990-71-9, 53990-72-0

(5aS,10aS)-octahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione

602-09-5

1,1'-bi-2-naphthol

A

C20H14O2*C10H14N2O2

18531-94-7

(R)-1,1'-Bi-2-naphthol

Conditions
ConditionsYield
In ethyl acetate for 2h; Reflux; Resolution of racemate; Green chemistry;A n/a
B 96%
602-09-5

1,1'-bi-2-naphthol

18531-94-7

(R)-1,1'-Bi-2-naphthol

18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

Conditions
ConditionsYield
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%
135-19-3

β-naphthol

18531-94-7

(R)-1,1'-Bi-2-naphthol

18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

Conditions
ConditionsYield
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

A

N-(2-chlorooctyl)-3,5-dinitrobenzamide

18531-94-7

(R)-1,1'-Bi-2-naphthol

Conditions
ConditionsYield
With boron trichloride In n-heptane; dichloromethane at 25℃; for 24h; Inert atmosphere;A 76%
B 85%
135-19-3

β-naphthol

18531-94-7

(R)-1,1'-Bi-2-naphthol

Conditions
ConditionsYield
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)

100-58-3

phenylmagnesium bromide

18531-94-7

(R)-1,1'-Bi-2-naphthol

B

4850-72-0

(-)-(S)-tert-butyl phenyl sulfoxide

Conditions
ConditionsYield
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

18531-94-7

(R)-1,1'-Bi-2-naphthol

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

(R)-(+)-1-(2-hydroxynapthalen-1-yl)napthalen-2-yl acetate

18531-94-7

(R)-1,1'-Bi-2-naphthol

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

(R)-(+)-1,1'-Bi-2-naphthol Specification

(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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