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Merck
CN

256269

(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
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
24855513
MDL number:
MFCD00064255
Beilstein/REAXYS Number:
2330888

Key Documents

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Product Name

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

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

SMILES string

O[C@H]([C@@H](O)c1ccccc1)c2ccccc2

InChI key

IHPDTPWNFBQHEB-KBPBESRZSA-N

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

Quality Level

200

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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.

General description

Chiral reagent.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000365851
0000365850
0000365851
0000365850
0000285551

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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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