938920
4′-Hydroxy-4,5-dimethoxy-[1,1′-biphenyl]-2-carbonitrile
Synonym(s):
Maiti-Maji Auxiliary
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About This Item
Empirical Formula (Hill Notation):
C15H13NO3
CAS Number:
Molecular Weight:
255.27
UNSPSC Code:
12352142
NACRES:
NA.21
Form:
powder
InChI key
LMDUSGRXYIRJDS-UHFFFAOYSA-N
SMILES string
COC1=C(OC)C=C(C2=CC=C(O)C=C2)C(C#N)=C1
form
powder
color
light beige
functional group
nitrile
storage temp.
−20°C
Quality Level
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.
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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H-bonded reusable template assisted para-selective ketonisation using soft electrophilic vinyl ethers
Maji, Arun et. al.
Nature Communications, 9(1) (2018)
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