294535
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:
Molecular Weight:
214.26
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Product Name
meso-Hydrobenzoin, 99%
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+
SMILES string
O[C@H]([C@H](O)c1ccccc1)c2ccccc2
InChI key
IHPDTPWNFBQHEB-OKILXGFUSA-N
assay
99%
form
solid
mp
137-139 °C (lit.)
solubility
ethanol: soluble 25 mg/mL, clear, colorless
functional group
hydroxyl
phenyl
Quality Level
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Application
meso-Hydrobenzoin has been used in the preparation of trans-methyl meso-hydrobenzoin phosphite.
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.
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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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
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)
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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