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Merck
CN

940984

N-(2,6-Dimethylphenyl)-6-hydroxypicolinamide

>95%

Synonym(s):

6-Hydroxy picolinohydrazide, N-(2,6-Dimethylphenyl)-6-oxo-1H-pyridine-2-carboxamide, MPBS

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About This Item

Empirical Formula (Hill Notation):
C14H14N2O2
CAS Number:
Molecular Weight:
242.27
MDL number:
NACRES:
NA.21
Assay:
>95%
Form:
powder
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SMILES string

O=C1C=CC=C(N1)C(=O)NC=2C(=CC=CC2C)C

InChI key

RLTMFMKUMLGROY-UHFFFAOYSA-N

InChI

InChI=1S/C14H14N2O2/c1-9-5-3-6-10(2)13(9)16-14(18)11-7-4-8-12(17)15-11/h3-8H,1-2H3,(H,15,17)(H,16,18)

assay

>95%

form

powder

color

white to off-white

Quality Level

General description

N-(2,6-Dimethylphenyl)-6-hydroxypicolinamide is a picolinamide ligand commonly used in copper catalyzed reactions.

Application

The ligand has been used in:

  • The Cu-catalyzed sulfonamidation of (hetero)aryl halides
  • The Cu-catalyzed cross coupling of primary amines and (hetero)aryl bromides
  • Cu-catalyzed hydroxylation reactions of (hetero)aryl halides in water
  • The synthesis of biaryl amines via the coupling of anilines and (hetero)aryl halides

Features and Benefits

Picolinamide ligands are useful in a range of Cu catalyzed cross coupling reactions. Such reactions often offer advantages over conventional palladium or Nickel catalyzed cross coupling reactions, such as:
  • Lower metal costs
  • Lower metal toxicity
  • Better substrate scope

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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