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294535

Sigma-Aldrich

meso-Hydrobenzoin

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
MDL number:
MFCD00064253
UNSPSC Code:
12352100
PubChem Substance ID:
24857719
NACRES:
NA.22

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

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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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Certificates of Analysis (COA)

Lot/Batch Number
STBJ9205
STBJ4659
STBF8007V
STBD1481V
STBD0597V

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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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