938912
2-(8-Nitroquinolin-3-yl)phenol
≥95%
Synonym(s):
Maiti-Dutta Auxiliary
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About This Item
Empirical Formula (Hill Notation):
C15H10N2O3
CAS Number:
Molecular Weight:
266.25
NACRES:
NA.21
Assay:
≥95%
Form:
powder, crystals or chunks
Quality Level
SMILES string
OC1=CC=CC=C1C2=CC3=C(N=C2)C([N+]([O-])=O)=CC=C3
InChI key
RUZNVXSAYJRSDE-UHFFFAOYSA-N
InChI
1S/C15H10N2O3/c18-14-7-2-1-5-12(14)11-8-10-4-3-6-13(17(19)20)15(10)16-9-11/h1-9,18H
assay
≥95%
form
powder, crystals or chunks
color
faint yellow to dark yellow
storage temp.
−20°C
General description
2-(8-Nitroquinolin-3-yl)phenol is an effective temporary directing group (TDG) for meta directed C-H functionalization, leading to selective alkenylation and acetoxylation of various arenes.
Application
2-(8-Nitroquinolin-3-yl)phenol is 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
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Catalytic Arene meta-C?H Functionalization Exploiting a Quinoline-Based Template
Dutta U, et al.
ACS Catalysis, 7, 3162?3168-3162?3168 (2017)
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