395242

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

99%

• Empirical Formula (Hill Notation): C₄₇H₃₈O₄
• CAS Number: 171086-52-5
• Molecular Weight: 666.80
• UNSPSC Code: 12352005
• PubChem Substance ID: 24864650
• NACRES: NA.22

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.

Safety Information

• Storage Class Code: 11 - 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