930067
2-(Pyrimidin-5-yl)benzaldehyde
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About This Item
Empirical Formula (Hill Notation):
C11H9N2O
Molecular Weight:
185.20
UNSPSC Code:
12352101
NACRES:
NA.06
MDL number:
form
powder or chunks
Quality Segment
mp
119-120 °C
functional group
aldehyde
storage temp.
−20°C
SMILES string
n1cncc(c1)c2c(cccc2)C=O
InChI
1S/C11H8N2O/c14-7-9-3-1-2-4-11(9)10-5-12-8-13-6-10/h1-8H
InChI key
JPSJBEALHNYNBL-UHFFFAOYSA-N
Application
2-(Pyrimidin-5-yl)benzaldehyde 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.
2-(pyrimidin-5-yl)benzaldehyde is an effective TDG for meta directed C-H functionalization of amine substituted target compounds, with high selectivity.
2-(pyrimidin-5-yl)benzaldehyde is an effective TDG for meta directed C-H functionalization of amine substituted target compounds, with high selectivity.
Other Notes
Imine as a linchpin approach for meta-C–H functionalization
https://www.nature.com/articles/s41570-021-00311-3">Transient directing ligands for selective metal-catalysed C–H activation
https://www.nature.com/articles/s41570-021-00311-3">Transient directing ligands for selective metal-catalysed C–H activation
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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