(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL

(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Property

Melting point:

92-96 °C(lit.)

alpha 

+85° (c 0.22, CHCl3)

Boiling point:

477.8±45.0 °C(Predicted)

Density 

1.182±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Toluene

form 

Powder

color 

white

optical activity

[α]20/D +92°, c = 1% in chloroform

Safety

Hazard Codes 

Xi,N

Risk Statements 

41-50/53

Safety Statements 

26-39-60-61-36/39-25

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

HS Code 

29093090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL Chemical Properties,Usage,Production

Reaction

Starting material for the preparation of a variety of 3,3'-substituted binaphthols.

Chemical Properties

Colorless solid

Uses

3- or 3,3′-di-substituted products can be obtained easily via ortho-metallation and subsequent treatment with an electrophile to give the corresponding BINOL derivatives.

Uses

An intermediate in the symmetric synthesis of BINOL-terpyridine ligands.

Synthesis

Sodium hydride (NaH, 1.92 g, 80 mmol) was slowly added to N,N-dimethylformamide (DMF, 30 mL) under ice bath conditions. Subsequently, a tetrahydrofuran (THF, 50 mL) solution of 1,1'-bi-2-naphthol (BINOL, 10 g, 34 mmol) was added slowly dropwise to the above mixture for 20 min. after 30 min, chloromethyl methyl ether (6.4 g, 80 mmol) was added slowly dropwise for the same period of time. The reaction process was monitored by thin layer chromatography (TLC). The reaction mixture was extracted with chloroform and water after stirring for 1 h. The organic layer was separated to obtain the crude product. The crude product was further purified by silica gel column chromatography with petroleum ether/ethyl acetate (5:1, v/v) as eluent. Finally, (R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl was obtained in 90% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.95-7.93 (d, J = 9.6 Hz, 2H), 7.87-7.85 (d, J = 8.4 Hz, 2H), 7.58-7.56 (d, J = 9.6 Hz, 2H), 7.35-7.31 (m, 2H), 7.23-7.14 (m, 4H ), 5.08-4.96 (q, J = 6.8 Hz, 4H), 3.13 (s, 6H).

References

[1] Organic Letters, 2004, vol. 6, # 16, p. 2701 - 2704
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 19, p. 2161 - 2166
[3] Chemistry - A European Journal, 2018, vol. 24, # 48, p. 12607 - 12612
[4] Chemistry Letters, 1995, # 12, p. 1113 - 1114
[5] Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 685 - 690