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930075

Sigma-Aldrich

2-fluoro-6-(pyrimidin-5-yl)aniline

≥95%

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About This Item

Empirical Formula (Hill Notation):
C10H8FN3
CAS Number:
1697040-97-3
Molecular Weight:
189.19
UNSPSC Code:
12352106
NACRES:
NA.06

Quality Level

100

Assay

≥95%

form

powder, crystals or chunks

color

light yellow

storage temp.

−20°C

SMILES string

NC1=C(C2=CN=CN=C2)C=CC=C1F

Application

2-fluoro-6-(pyrimidin-5-yl)aniline 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-fluoro-6-(pyrimidin-5-yl)aniline is an effective TDG for meta directed C-H functionalization of aldehyde substituted target compounds, with high selectivity.

Other Notes

1. Imine as a linchpin approach for meta-C–H functionalization2. Transient directing ligands for selective metal-catalysed C–H activation

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Sukdev Bag et al.
Nature communications, 12(1), 1393-1393 (2021-03-04)
Despite the widespread applications of C-H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing groups (DGs) served as ancillary ligands to ensure ortho-, meta- and para-C-H functionalization over the last two decades. These covalently linked DGs necessitate
Zhen Li et al.
Science (New York, N.Y.), 372(6549), 1452-1457 (2021-11-30)
Hydroxylation of aryl carbon-hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to

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