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482846

Sigma-Aldrich

(S,S)-(−)-1,2-Di(1-naphthyl)-1,2-ethanediol

98%

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About This Item

Linear Formula:
[C10H7CH(OH)-]2
CAS Number:
229184-99-0
Molecular Weight:
314.38
MDL number:
MFCD01863520
UNSPSC Code:
12352005
PubChem Substance ID:
24871848
NACRES:
NA.22

assay

98%

optical activity

[α]23/D −25°, c = 1 in chloroform

mp

149-151 °C (lit.)

SMILES string

O[C@H]([C@@H](O)c1cccc2ccccc12)c3cccc4ccccc34

InChI

1S/C22H18O2/c23-21(19-13-5-9-15-7-1-3-11-17(15)19)22(24)20-14-6-10-16-8-2-4-12-18(16)20/h1-14,21-24H/t21-,22-/m0/s1

InChI key

MNRCSHSTIWDUPJ-VXKWHMMOSA-N

Application

(S, S)-(-)-1,2-Di(1-naphthyl)-1,2-ethanediol can be used as:
  • A ligand in the asymmetric sulfoxidation of dihydrothienopyrimidine.[1]
  • A reactant for the preparation of (2S,2′S)-[(1S,2S)-1,2-bis(naphthalen-1-yl)ethane-1,2-diyl] bis[2-(dimethylamino)propanoate], a chiral bisester ligand via condensation reaction with N,N-dimethylamino acid using aldol-Tishchenko condensation catalyst.[2]
  • A reactant to synthesize diol-SnCl4 chiral Bronsted acid complex, which is employed as a catalyst in the allylboration of aldehydes.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
08227BS

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Asymmetric Oxidation of a Dihydrothienopyrimidine
Rodriguez S, et al.
Organic Process Research & Development, 21(3), 444-447 (2017)
Catalytic Enantioselective and Catalyst-Controlled Diastereofacial-Selective Additions of Allyl-and Crotylboronates to Aldehydes Using Chiral Bronsted Acids
Rauniyar V and Hall DG
Angewandte Chemie (International Edition in English), 45(15), 2426-2428 (2006)
Synthesis of Yb Complexes with Amino-Acid-Armed Ligands for Direct Asymmetric Tandem Aldol Reduction Reactions
Stodulski M, et al.
European Journal of Organic Chemistry, 2008(33), 5553-5562 (2008)

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