Key Documents

395242

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol

Name: (4<I>S-trans</I>)-2,2-Dimethyl-<I>α,α,α′,α′</I>-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol
Brand: ALDRICH

99%

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About This Item

Empirical Formula (Hill Notation):

C₄₇H₃₈O₄

CAS Number:

171086-52-5

Molecular Weight:

666.80

UNSPSC Code:

12352005

PubChem Substance ID:

24864650

NACRES:

NA.22

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Properties

assay

99%

form

solid

optical activity

[α]20/D +280°, c = 1 in ethyl acetate

mp

200 °C (dec.) (lit.)

functional group

ether, hydroxyl, ketal

SMILES string

CC1(C)O[C@@H]([C@H](O1)C(O)(c2cccc3ccccc23)c4cccc5ccccc45)C(O)(c6cccc7ccccc67)c8cccc9ccccc89

InChI

1S/C47H38O4/c1-45(2)50-43(46(48,39-27-11-19-31-15-3-7-23-35(31)39)40-28-12-20-32-16-4-8-24-36(32)40)44(51-45)47(49,41-29-13-21-33-17-5-9-25-37(33)41)42-30-14-22-34-18-6-10-26-38(34)42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1

InChI key

WTZVNZRNIOJACO-CXNSMIOJSA-N

Description

Application

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol, also known as TADDOL, is a chiral auxiliary that can be used:

For the highly enantioselective addition of primary alkyl Grignards to ketones.
As an organocatalyst for the activation of carbonyl functionality in vinylogous addition reaction of an aldehyde.
As a chiral dopant in the preparation of cholesteric liquid crystal (CLC) having an aggregation-induced-emission dye.

Storage Class

11 - 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

14131KZ

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Articles

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

Chiral Diols

TADDOLs demonstrate versatility in metal-catalyzed asymmetric reactions and as Brønsted acid organocatalysts in hetero-Diels–Alder reactions.

Lasing properties of a cholesteric liquid crystal containing aggregation-induced-emission material

Wang N, et al.

Optics Express, 23(26), 33938-33946 (2015)

Angewandte Chemie (International Edition in English), 31, 84-84 (1992)

Global Trade Item Number

SKU	GTIN
395242-1G	04061826094860