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802166

Sigma-Aldrich

2-(Pyridin-2-yl)isopropyl amine

95% (GC)

Synonym(s):

PIP, PIP Directing Group, Shi Auxilliary

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About This Item

Empirical Formula (Hill Notation):
C8H12N2
CAS Number:
52568-28-2
Molecular Weight:
136.19
MDL number:
MFCD08729302
UNSPSC Code:
12352100
PubChem Substance ID:
329768731

description

Fp: 175°F

Quality Level

100

Assay

95% (GC)

form

liquid

reaction suitability

reagent type: catalyst
reagent type: ligand
reaction type: C-H Activation

refractive index

n/D 1.516

density

0.9800 g/mL at 25 °C

SMILES string

NC(C)(C)C1=CC=CC=N1

InChI

1S/C8H12N2/c1-8(2,9)7-5-3-4-6-10-7/h3-6H,9H2,1-2H3

InChI key

DQSQBZXDMHDHEO-UHFFFAOYSA-N

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General description

2-(Pyridin-2-yl)isopropyl amine (PIP-amine) is a tertiary amine. A bidentate directing group, useful for the functionalization of C-H bond, has been developed from PIP-amine.

Application

The Shi Auxiliary is a powerful directing group for the hydroxylation of arenes through copper-mediated C-H activation. This useful auxiliary can be removed through acid-mediated hydrolysis and has shown to be done on gram-scale.

Other Notes

Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 - H315 - H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

175.0 °F

Flash Point(C)

79.44 °C

Certificates of Analysis (COA)

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Xin Li et al.
Organic letters, 16(15), 3904-3907 (2014-07-17)
A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the

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