(R)-(+)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL Chemical Properties

Melting point:

126 °C

Boiling point:

452.3±40.0 °C(Predicted)

Density 

1.196±0.06 g/cm3(Predicted)

refractive index 

220 ° (C=1, EtOH)

storage temp. 

Sealed in dry,Room Temperature

solubility 

sol dichloromethane, chloroform, THF, ethanol; insol hexane.

form 

powder to crystal

pka

12.87±0.29(Predicted)

color 

White to Almost white

optical activity

217.3° (C=1.02 g/100ml,ETOH)

InChI

InChI=1S/C20H18O2/c21-19(16-10-4-1-5-11-16)20(22,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19,21-22H/t19-/m1/s1

InChIKey

GWVWUZJOQHWMFB-LJQANCHMSA-N

SMILES

C(C1=CC=CC=C1)(C1=CC=CC=C1)(O)[C@@H](C1=CC=CC=C1)O

Safety Information

HS Code 

29062990

(R)-(+)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL Usage And Synthesis

Uses

(R)-(+)-1,1,2-triphenyl-1,2-ethanediol can be used to derivatize chiral monoesters via stereoselective aldol addition; forming O-silyl orthoesters and cyclic phosphonates.

Preparation

(R)-1,1,2-triphenylethane-1,2-diol [(R)-(1)] is easily available from commercial (R)-Mandelic Acid, which is  first esterified to give methyl mandelate and then treated with Phenylmagnesium Bromide (3.5 equiv). In an analogous way, (S)-(1)  is accessible from (S)-mandelic acid, which is also commercially available (eq 1).

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 493, 1959 DOI: 10.1021/ja01511a058
Synthesis, p. 415, 1987
Tetrahedron, 49, p. 1327, 1993 DOI: 10.1016/S0040-4020(01)85822-1

(R)-(+)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL(95061-46-4)Related Product Information

• Triphenylethylene
• 1-Phenyl-1,2-ethanediol
• ( S)-(+)-1,2,2-TRIPHENYL-1,2-ETHANEDIOL 2-ACETATE
• ( R)-(+)-1,2,2-TRIPHENYL-1,2-ETHANEDIOL 2-ACETATE
• (S)-(-)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL,(S)-1,2,2-Triphenyl-1,2-ethanediol,(S)-(-)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL 99%
• (S)-(-)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL 2-ACETATE
• 1,1,2,2-TETRAKIS(4-METHOXYPHENYL)-1,2-ETHANEDIOL
• Benzopinacole
• 1,1,2-triphenyl-1,2-ethanediol-2-acetate,(R)-(+)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL 2-ACETATE
• 3,3',3'',3'''-TETRAKIS(TRIFLUOROMETHYL)BENZOPINACOLE
• (R)-(+)-1,1,2-TRIPHENYL-1,2-ETHANEDIOL
• 1,1,2,2-TETRAKIS(4-METHYLPHENYL)-1,2-ETHANEDIOL