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Merck

930067

Sigma-Aldrich

2-(Pyrimidin-5-yl)benzaldehyde

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About This Item

经验公式(希尔记法):
C11H9N2O
分子量:
185.20
MDL號碼:
分類程式碼代碼:
12352101
NACRES:
NA.06

形狀

powder or chunks

品質等級

mp

119-120 °C

官能基

aldehyde

儲存溫度

−20°C

應用

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.

其他說明

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

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象形圖

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訊號詞

Warning

危險分類

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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Transient directing ligands for selective metal-catalysed C?H activation
Nupur, et al.
Nature Reviews Chemistry, 5, 646?659-646?659 (2021)
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

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