938920

4′-Hydroxy-4,5-dimethoxy-[1,1′-biphenyl]-2-carbonitrile

• Synonym(s): Maiti-Maji Auxiliary
• Empirical Formula (Hill Notation): C₁₅H₁₃NO₃
• CAS Number: 2145079-91-8
• Molecular Weight: 255.27
• UNSPSC Code: 12352142

Properties

• form: powder
• Quality Level: 100
• color: light beige
• functional group: nitrile
• storage temp.: −20°C
• SMILES string: COC1=C(OC)C=C(C2=CC=C(O)C=C2)C(C#N)=C1
• InChI key: LMDUSGRXYIRJDS-UHFFFAOYSA-N

Description

General description

4′-Hydroxy-4,5-dimethoxy-[1,1′-biphenyl]-2-carbonitrile is an effective temporary directing group (TDG) for meta directed C-H functionalization, effective in many transformations including olefination, silylation, and cyanation of arenes.

Application

A temporary directing group (TDG) to assist as a co-catalyst for metal catalyzed C-H functionalization. Often in C-H functionalization, an auxiliary compound is used to control site selectivity. These traditionally are covalently bonded to the compound of interest, and must subsequently be removed after functionalization, like a typical protecting group. To simplify the process of C-H functionalization, 2-fluoro-6-(pyrimidin-5-yl)aniline is one of a series of temporary directing groups developed by Deb Maiti′s lab that promote site selectivity without the inclusion of additional synthetic steps.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable