256269
(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:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
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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.
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)
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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)
Burk, M.J. et al.
Journal of the American Chemical Society, 115, 10125-10125 (1993)
Chromatograms
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