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Sigma-Aldrich

(S,S)-(−)-Hydrobenzoin

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

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Synonym(s):
(S,S)-(−)-1,2-Diphenyl-1,2-ethanediol, (S,S)-1,2-Diphenylethylene glycol
Linear Formula:
C6H5CH(OH)CH(OH)C6H5
CAS Number:
Molecular Weight:
214.26
Beilstein:
2330888
MDL number:
PubChem Substance ID:
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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This Item
302155115568301426
Hydrobenzoin

Sigma-Aldrich

301426

Hydrobenzoin

mp

148-150 °C (lit.)

mp

64-67 °C (lit.)

mp

-

mp

-

optical activity

[α]24/D −94°, c = 2.5 in ethanol

optical activity

[α]18/D +66°, c = 1 in chloroform

optical activity

[α]20/D −39°, neat

optical activity

-

optical purity

ee: 99% (GLC)

optical purity

-

optical purity

ee: 98% (GLC)

optical purity

-

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

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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)
Marshall, J.A. Xie, S.
The Journal of Organic Chemistry, 60, 7230-7230 (1995)
Matteson, D.S. Man, H.-W.
The Journal of Organic Chemistry, 59, 5734-5734 (1994)

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