Skip to Content
Merck
All Photos(1)

Documents

802166

Sigma-Aldrich

2-(Pyridin-2-yl)isopropyl amine

95% (GC)

Synonym(s):

PIP, PIP Directing Group, Shi Auxilliary

Sign Into View Organizational & Contract Pricing
All Photos(1)

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
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service