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

ALDRICH/901251

Synonym: PPA directing group

CAS Number: 4392-87-4 (free base)
Empirical Formula (Hill Notation): C11H8N2O2 · xHCl
Molecular Weight: 200.19 (free base basis)
MDL Number: MFCD11100046
Linear Formula: C11H8N2O2 · xHCl
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-901251-500MG 500 mg
 $166.00
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 901251-500MG.

 

form powder or crystals
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
Quality Level 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
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 
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
UNSPSC 12352101

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