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256269

Sigma-Aldrich

(S,S)-(−)-Hydrobenzoin

99%, optical purity ee: 99% (GLC)

Synonym(s):

(S,S)-(−)-1,2-Diphenyl-1,2-ethanediol, (S,S)-1,2-Diphenylethylene glycol

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About This Item

Linear Formula:
C6H5CH(OH)CH(OH)C6H5
CAS Number:
2325-10-2
Molecular Weight:
214.26
Beilstein:
2330888
MDL number:
MFCD00064255
UNSPSC Code:
12352002
PubChem Substance ID:
24855513
NACRES:
NA.22

Assay

99%

optical activity

[α]24/D −94°, c = 2.5 in ethanol

optical purity

ee: 99% (GLC)

mp

148-150 °C (lit.)

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-/m0/s1

InChI key

IHPDTPWNFBQHEB-KBPBESRZSA-N

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General description

Chiral reagent.

Application

(S,S)-(-)-Hydrobenzoin may also be used to prepare (1S,2S,1′S)- and (1S,2S,1′R)-2-(cyclohex-2′-enyloxy)-1,2-diphenylethanol, which are intermediates to prepare enantiopure cyclohexitols. The (S,S)-(-)-hydrobenzoin/Ca complex may be used to catalyze the direct asymmetric aldol reaction of acetophenone and pivalaldehyde to form (R)-3-hydroxy-4,4-dimethyl-1-phenylpentan-1-one.
C2 symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catalytic asymmetric aldol reaction of ketones and aldehydes using chiral calcium alkoxides.
Tetrahedron Letters, 42(28), 4669-4671 (2001)
Synthesis of enantiopure cyclitols from (?)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S, S)-hydrobenzoin and (S)-mandelic acid as chiral sources.
Lee YJ, et al.
Tetrahedron, 61(8), 1987-2001 (2005)
Stolle, A. et al.
Tetrahedron Letters, 35, 3521-3521 (1994)
Burk, M.J. et al.
Journal of the American Chemical Society, 115, 10125-10125 (1993)
Burk, M.J. et al.
Tetrahedron Asymmetry, 2, 569-569 (1991)
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Chromatograms

application for HPLC

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