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294535

Sigma-Aldrich

meso-Hydrobenzoin

99%

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Synonym(s):
meso-1,2-Diphenyl-1,2-ethanediol
Linear Formula:
C6H5CH(OH)CH(OH)C6H5
CAS Number:
Molecular Weight:
214.26
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

mp

137-139 °C (lit.)

solubility

ethanol: soluble 25 mg/mL, clear, colorless

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

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This Item
102466S4808256269
meso-Hydrobenzoin 99%

Sigma-Aldrich

294535

meso-Hydrobenzoin

Ethylene glycol ReagentPlus®, ≥99%

Sigma-Aldrich

102466

Ethylene glycol

cis-Stilbene 96%

Sigma-Aldrich

S4808

cis-Stilbene

form

solid

form

liquid

form

-

form

-

mp

137-139 °C (lit.)

mp

−13 °C (lit.)

mp

-

mp

148-150 °C (lit.)

solubility

ethanol: soluble 25 mg/mL, clear, colorless

solubility

water: miscible

solubility

-

solubility

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)

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