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676551

Sigma-Aldrich

Potassium 2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-2,2-diphenylacetate

95%

Synonym(s):

Potassium N-(3,5-di-tert-butylsalicylidene)-2-amino-2,2-diphenylacetate, SALDIPAC

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About This Item

Empirical Formula (Hill Notation):
C29H32KNO3
Molecular Weight:
481.67
UNSPSC Code:
12352300
PubChem Substance ID:
24884856
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reagent type: ligand

mp

122.2-131.9 °C

SMILES string

CC(C)(C)c1cc(\C=N\C(C(=O)O[K])(c2ccccc2)c3ccccc3)c(O)c(c1)C(C)(C)C

InChI

1S/C29H33NO3.K/c1-27(2,3)23-17-20(25(31)24(18-23)28(4,5)6)19-30-29(26(32)33,21-13-9-7-10-14-21)22-15-11-8-12-16-22;/h7-19,31H,1-6H3,(H,32,33);/q;+1/p-1/b30-19+;

InChI key

ZPKNCDGWTMRAKF-QUIZVCAPSA-M

Application

Hydroazidation Catalyst for Facile Preparation of Organoazides

SALDIPAC ligand used with Co(BF4)2 (cat. no. 399957) in a hydroazidation of unactivated olefins providing a simple synthesis of alkylazides. The azides, in turn, can be used in a copper-catalyzed cycloaddition with acetylenes providing 1,4-disubstitutedtriazoles.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBC9657
10312JE

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Synthesis, 3839-3839 (2007)
Jérôme Waser et al.
Journal of the American Chemical Society, 127(23), 8294-8295 (2005-06-09)
Conversion of olefins to azides was achieved with high Markovnikov selectivity for a broad range of alkenes using 6 mol % Co(BF4).6H2O and ligand 1, with 3 equiv of TsN3 as nitrogen source and simple silanes (PhSiH3, TMDSO).

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