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Sigma-Aldrich

(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:
52340-78-0
Molecular Weight:
214.26
Beilstein/REAXYS Number:
2050815
MDL number:
MFCD00064254
UNSPSC Code:
12352002
PubChem Substance ID:
24855514
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

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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)
A practical stereoselective synthesis of chiral hydrobenzoins via asymmetric transfer hydrogenation of benzils.
Murata K, et al.
Organic Letters, 1(7), 1119-1121 (1999)

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