171086-52-5

Basic information

• Product Name: (4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&
• Synonyms: (4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&;(4S-TRANS)-2,2-DIMETHYL-A,A,A',A'-TETRA( 1-NAPHTHYL)-1,3-DIOXOLANEDIMETHANOL, 99%;(4s-trans)-2,2-dimethyl-α,α,α',α'-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol;(4S,5S)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetra(1-nephthyl)-1,3-dioxolane-4,5-dimethanol;(4S-trans)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol 99%;(4S,5S)-2,2-dimethyl-α4,α4,α5,α5-tetra-1-naphthalenyl-1,3-Dioxolane-4,5-dimethanol;(4S,5S)-(-)-2,2-Dimethyl-α,α,α',α'-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol,98%;(4S,5S)-2,2-Dimethyl-α,α,α',α'-tetra(1-naphthyl)-1,3- dioxolane-4,5-dimethanol,99%e.e.
• CAS NO: 171086-52-5
• Molecular Formula: C47H38O4
• Molecular Weight: 666.80222
• Product Categories: Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes;TADDOLs;Chiral Oxygen;TADDOL Series
• Mol File: 171086-52-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 200 °C (dec.)(lit.)
• Appearance: /
• Density: 1.27g/cm3
• PKA: 12.00±0.29(Predicted)
• CAS DataBase Reference: (4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&(CAS DataBase Reference)
• NIST Chemistry Reference: (4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&(171086-52-5)
• EPA Substance Registry System: (4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&(171086-52-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 171086-52-5(Hazardous Substances Data)

Usage

Description

(4S-TRANS)-2 2-DIMETHYL-A A A' A'-TETRA&, also known as TADDOL, is a chiral auxiliary with a unique structure that consists of four 1-naphthyl groups attached to a 1,3-dioxolane-4,5-dimethanol core. This molecular configuration endows TADDOL with exceptional properties, making it a versatile compound in various applications across different industries.

Uses

Used in Chemical Synthesis:
TADDOL is used as a chiral auxiliary in the highly enantioselective addition of primary alkyl Grignards to ketones. Its unique structure allows for the efficient and selective formation of chiral alcohols, which are crucial in the synthesis of pharmaceuticals and other biologically active compounds.
Used in Organocatalysis:
TADDOL serves as an organocatalyst for the activation of carbonyl functionality in the vinylogous addition reaction of an aldehyde. This application enables the development of new synthetic routes and the production of complex molecules with high enantioselectivity.
Used in Liquid Crystal Preparation:
TADDOL is used as a chiral dopant in the preparation of cholesteric liquid crystals (CLCs) that possess aggregation-induced-emission dye properties. These CLCs have potential applications in the development of advanced display technologies and sensors.