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Merck
CN

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:
52340-78-0
Molecular Weight:
214.26
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
24855514
MDL number:
MFCD00064254
Beilstein/REAXYS Number:
2050815

Key Documents

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Product Name

(R,R)-(+)-Hydrobenzoin, 99%, optical purity ee: 99% (HPLC)

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

SMILES string

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

InChI key

IHPDTPWNFBQHEB-ZIAGYGMSSA-N

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.)

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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.

General description

(R,R)-(+)-Hydrobenzoin is a chiral 1,2-diol useful as a chiral reagent, building block, ligand or auxiliary in asymmetric synthesis.

Storage Class

13 - Non 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
0000117213
0000117213
0000137213
0000134430
0000052688

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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)
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)
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)

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