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294535

meso-Hydrobenzoin

Name: <I>meso</I>-Hydrobenzoin
Brand: ALDRICH

99%

Synonym(s):

meso-1,2-Diphenyl-1,2-ethanediol

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About This Item

Linear Formula:

C₆H₅CH(OH)CH(OH)C₆H₅

CAS Number:

579-43-1

Molecular Weight:

214.26

NACRES:

NA.22

PubChem Substance ID:

24857719

UNSPSC Code:

12352100

MDL number:

MFCD00064253

Assay:

99%

Form:

solid

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Properties

Quality Level

100

assay

99%

form

solid

mp

137-139 °C (lit.)

solubility

ethanol: soluble 25 mg/mL, clear, colorless

functional group

hydroxyl, phenyl

SMILES string

O[C@H]([C@H](O)c1ccccc1)c2ccccc2

InChI

1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14+

InChI key

IHPDTPWNFBQHEB-OKILXGFUSA-N

Description

General description

Desymmetrization of meso-hydrobenzoin using chiral phosphine catalyst has been reported. Conversion of meso-hydrobenzoin to trans-stillbene oxide by treatment with an aryl sulfonyl chloride and aqueous sodium hydroxide has been reported.

Application

meso-Hydrobenzoin has been used in the preparation of trans-methyl meso-hydrobenzoin phosphite.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Conversion of meso-Hydrobenzoin with Arylsulfonyl Chlorides and Base to trans-Stilbene Oxide and to 1, 1-Diphenyl-2-(p-toluenesulfonyloxy) ethylene1.

Curtin DY and Hendrickson YG.

The Journal of Organic Chemistry, 21(11), 1260-1263 (1956)

Desymmetrization of meso-hydrobenzoin using chiral, nucleophilic phosphine catalysts.

E Vedejs et al.

The Journal of organic chemistry, 69(4), 1389-1392 (2004-02-14)

The desymmetrization of meso-hydrobenzoin is described using chiral phosphine catalysts 8b-d and 9-11. The best enantioselectivity at room temperature was obtained with the newly synthesized phospholane 8c and benzoic anhydride, but the reaction is very slow. Much faster reactions, but

Preparation and crystal structures of trans-methyl meso-hydrobenzoin phosphite and phosphate.

Newton MG and Campbell BS.

Journal of the American Chemical Society, 96(25), 7790-7797 (1974)

Global Trade Item Number

SKU	GTIN
294535-25G	04061832279763
294535-5G	04061832279770