(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

pka

9.62±0.20(Predicted)

color 

off-white

optical activity

[α]20/D +73°, c = 1 in THF

Sensitive 

Hygroscopic

CAS DataBase Reference

65355-14-8

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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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

Chemical Properties

white 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 (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(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