802166
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:
Molecular Weight:
136.19
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
95% (GC)
Form:
liquid
InChI
1S/C8H12N2/c1-8(2,9)7-5-3-4-6-10-7/h3-6H,9H2,1-2H3
SMILES string
NC(C)(C)C1=CC=CC=N1
InChI key
DQSQBZXDMHDHEO-UHFFFAOYSA-N
description
Fp: 175°F
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
functional group
amine
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
175.0 °F
flash_point_c
79.44 °C
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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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