256277
(R,R)-(+)-Hydrobenzoin
99%, optical purity ee: 99% (HPLC)
Synonym(s):
(R,R)-1,2-Diphenyl-1,2-ethanediol, (R,R)-1,2-Diphenylethylene glycol
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About This Item
Linear Formula:
C6H5CH(OH)CH(OH)C6H5
CAS Number:
Molecular Weight:
214.26
Beilstein:
2050815
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
Assay
99%
form
solid
optical activity
[α]28/D +93°, c = 2.5 in ethanol
optical purity
ee: 99% (HPLC)
mp
146-149 °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-/m1/s1
InChI key
IHPDTPWNFBQHEB-ZIAGYGMSSA-N
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General description
(R,R)-(+)-Hydrobenzoin is a chiral 1,2-diol useful as a chiral reagent, building block, ligand or auxiliary in asymmetric synthesis.
Application
(R,R)-(+)-Hydrobenzoin may be used in the oxyselenenylation step in the multi-step synthesis of cyclopentitols and aminocyclopentitols from cyclopentene. It may also be used as a ligand for the asymmetric addition of diethylzinc to aldehydes in the presence or absence of titanium tetra-isopropoxide to form (R)- or (S)-form of the corresponding secondary alcohol, respectively.
Storage Class Code
13 - Non 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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A practical stereoselective synthesis of chiral hydrobenzoins via asymmetric transfer hydrogenation of benzils.
Murata K, et al.
Organic Letters, 1(7), 1119-1121 (1999)
Divergent enantioselective pathways in the catalytic asymmetric addition of diethylzinc to aldehydes in the presence and absence of titanium tetraisopropoxide.
Dean MA and Hitchcock SR.
Tetrahedron Asymmetry, 19(22), 2563-2567 (2008)
Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R, R)-hydrobenzoin.
Kim KS, et al.
Tetrahedron Letters, 39(36), 6471-6474 (1998)
Chromatograms
application for HPLC
application for HPLC
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