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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:
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 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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Certificates of Analysis (COA)

Lot/Batch Number
BGBB3489V
BGBB3489
BGBB2924V
BGBB2924
0001405237

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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)

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