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256277

(R,R)-(+)-Hydrobenzoin

Name: (<I>R,R</I>)-(+)-Hydrobenzoin
Brand: ALDRICH

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

Assay:

99%

Form:

solid

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Properties

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

Description

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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)

Global Trade Item Number

SKU	GTIN
256277-25G	04061832718941
256277-5G	04061832718958