(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL

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CAS:65355-14-8
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(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL manufacturers

(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL Basic information
Product Name:(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL
Synonyms:(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL;(R)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL;(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO(1,1'BINAPHTHALENE)-2,2'-DIOL;(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-BI-2-NAPHTHOL;(+/-)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL;(R)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthol, 98%e.e.;(R)-(+)-2,2'-DIHYDROXY-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BINAPHTHYL;(S)-(-)-5,5',6,6',7,7',8,8'-OCTAHYDRO(1,1'BINAPHTHALENE)-2,2'-DIOL
CAS:65355-14-8
MF:C20H22O2
MW:294.39
EINECS:
Product Categories:BINOL Series;Chiral Oxygen;BINOLs;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes
Mol File:65355-14-8.mol
(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL Structure
(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL Chemical Properties
Melting point 165-169 °C(lit.)
alpha +48° to 53° (c 1.1, CHCl3)
Boiling point 516.7±50.0 °C(Predicted)
density 1.200
refractive index 50 ° (C=1, CHCl3)
storage temp. Inert atmosphere,Room Temperature
solubility almost transparency in Chloroform
form Powder
pka9.62±0.20(Predicted)
color off-white
Optical Rotation[α]20/D +73°, c = 1 in THF
Sensitive Hygroscopic
CAS DataBase Reference65355-14-8
Safety Information
Hazard Codes Xi,N
Risk Statements 36-50/53-36/37/38
Safety Statements 26-60-61-36
RIDADR UN 3077 9/PG 3
WGK Germany 3
HS Code 29072990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL Usage And Synthesis
Chemical Propertieswhite powder
Uses(R)-(+)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-2-naphthol can be used:
  • As a starting material for the preparation of octahydro-binaphthyl based organic light-emitting diodes.
  • As a ligand in the 1,4-hydrophosphinylation of methyl cyclohexene-1-carboxylate using diphenylphosphine oxide, applicable in the synthesis of CyPHOX ligands.

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

18531-94-7

(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL

39648-74-3

(R)-1,1'-Bi-2-naphthol (70.52 mM) was used as starting material and added sequentially to an autoclave with platinum oxide (1.15 mM) and acetic acid (25 mL). The reaction was stirred at room temperature for 3 days in a hydrogen atmosphere of 6.8 atm. Upon completion of the reaction, the reaction was quenched by addition of water and dichloromethane. The reaction mixture was extracted three times with dichloromethane and the organic phases were combined. The organic phase was sequentially washed once with water and twice with saturated aqueous sodium bicarbonate and then dried with anhydrous sodium sulfate. After drying, the desiccant was removed by filtration and the filtrate was concentrated to afford the target product 5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol (70.74 mM, quantitative yield). The specific optical rotation of the product was [α]D26 +47.1 (c 1.04, CHCl3).1H NMR (400 MHz, CDCl3) δ= 7.06 (d, 2H, J = 8.2 Hz), 6.82 (d, 2H, J = 8.2 Hz), 4.60 (s, 2H), 2.75 (t, 4H, J = 6.2 Hz), 2.33- 2.25 (m, 2H), 2.19-2.12 (m, 2H), 1.77-1.64 (m, 8H).13C NMR (100 MHz, CDCl3) δ= 151.35, 137.12, 131.01, 130.08, 118.81, 112.93, 29.20, 27.08, 22.98, 22.92 .

References[1] Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 3220 - 3221
[2] Patent: EP1623971, 2006, A1. Location in patent: Page/Page column 28
[3] Molecules, 2018, vol. 23, # 9,
[4] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 10291 - 10293
[5] Chemistry - A European Journal, 2010, vol. 16, # 44, p. 13116 - 13126
(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL Preparation Products And Raw materials
Raw materials(R)-(+)-1,1'-Bi-2-naphthol-->Hydrogen-->Acetic acid
Tag:(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL(65355-14-8) Related Product Information
(R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL 1,1'-BINAPHTHYL 1,1'-Bi-2-naphthol (R)-(+)-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL 3,3'-DIBROMO-5,5',6,6',7,7',8,8'-OCTAHYDRO-1,1'-BI-2-NAPHTHOL

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