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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
Pricing and availability is not currently available.

Assay

99%

optical activity

[α]24/D −94°, c = 2.5 in ethanol

optical purity

ee: 99% (GLC)

mp

148-150 °C (lit.)

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-/m0/s1

InChI key

IHPDTPWNFBQHEB-KBPBESRZSA-N

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1 of 4

This Item
302155115568301426
(S,S)-(−)-Hydrobenzoin 99%, optical purity ee: 99% (GLC)

256269

(S,S)-(−)-Hydrobenzoin

(S)-(+)-1-Phenyl-1,2-ethanediol 99%

302155

(S)-(+)-1-Phenyl-1,2-ethanediol

(S)-(−)-α-Methylbenzylamine 98%

115568

(S)-(−)-α-Methylbenzylamine

Hydrobenzoin

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

-

functional group

hydroxyl

functional group

hydroxyl, phenyl

functional group

amine, phenyl

functional group

-

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.[1] 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.[2]
C2 symmetric chiral diol with versatile applications as a chiral auxiliary,[3][4] building block,[5][6][7] and chiral ligand.[8][9]

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
BGBC0918V
21797LJV
21797LJ
09331JJ
06301DJ

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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)
Marshall, J.A. Xie, S.
The Journal of Organic Chemistry, 60, 7230-7230 (1995)
Stolle, A. et al.
Tetrahedron Letters, 35, 3521-3521 (1994)
Pichon, M. Figadere, B.
Tetrahedron Asymmetry, 7, 927-927 (1996)
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Chromatograms

application for HPLC

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