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901251

[2,2′-Bipyridine]-6-carboxylic acid hydrochloride

Name: [2,2′-Bipyridine]-6-carboxylic acid hydrochloride
Brand: ALDRICH

Synonym(s):

PPA directing group

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₈N₂O₂ · xHCl

CAS Number:

4392-87-4

Molecular Weight:

200.19 (free base basis)

UNSPSC Code:

12352101

NACRES:

NA.22

MDL number:

MFCD11100046

Form:

powder or crystals

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Properties

form

powder or crystals

Quality Segment

100

reaction suitability

reaction type: C-C Bond Formation, reagent type: catalyst, reagent type: ligand
reaction type: C-H Activation

SMILES string

n1c(cccc1C(=O)O)c2ncccc2

InChI

1S/C11H8N2O2/c14-11(15)10-6-3-5-9(13-10)8-4-1-2-7-12-8/h1-7H,(H,14,15)

InChI key

ZQTILGDVDYWICD-UHFFFAOYSA-N

Description

Application

Developed in the Engle lab, this 2,2′-bipyridylamide (PPA) is a pincer-like, removable tridentate directing group that stabilizes 6-membered palladacycles for olefin functionalization. Together with similar ligand PAQ (901250), researchers demonstrated regioselective remote hydrocarbofunctionalization of alkene-containing substrate classes (e.g. 4-pentenoic acids, allylic alcohols, homoallyl amines, bis-homoallylamines) using Pd(II) catalysis.

Other Notes

Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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