Skip to Content
MilliporeSigma
All Photos(2)

Documents

901126

Sigma-Aldrich

trans-Bis(tribenzylphosphine)(2-methylphenyl)nickel(II) chloride

95%

Synonym(s):

trans-(PBn3)2Ni(o-tolyl)Cl

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C49H49ClNiP2
CAS Number:
1594112-87-4
Molecular Weight:
794.01
UNSPSC Code:
12352200

assay

95%

form

powder or solid

reaction suitability

reaction type: Cross Couplings
reagent type: catalyst

mp

200-205 °C

SMILES string

Cl[Ni](C1=C(C)C=CC=C1)(P(CC2=CC=CC=C2)(CC3=CC=CC=C3)CC4=CC=CC=C4)P(CC5=CC=CC=C5)(CC6=CC=CC=C6)CC7=CC=CC=C7

Application

The following Ni-complex is an air-stable precatalyst for various Ni-catalyzed reactions which normally require Ni(cod)2, however, this precatalyst will not require any glovebox or schlenk techniques that must be followed with Ni(cod)2. Rates are enhanced and selectivity is maintained when compared to the same reaction with Ni(cod)2.

Other Notes

Legal Information

Patent application PCT/US2014/064565. Sold under license from the Massachusetts Institute of Technology.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_c

Not applicable

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

Recent advances in homogeneous nickel catalysis.
Tasker S Z, et al.
Nature, 509(7500), 299-299 (2014)
Sarah Z Tasker et al.
Nature, 509(7500), 299-309 (2014-05-16)
Tremendous advances have been made in nickel catalysis over the past decade. Several key properties of nickel, such as facile oxidative addition and ready access to multiple oxidation states, have allowed the development of a broad range of innovative reactions.

Articles

Jamison Nickel (II) Precatalysts

The Jamison group has developed a library of bench-stable phosphine-containing nickel(II) precatalysts that are converted into active catalysts in situ.

Nickel and Nickel-based Compounds (Complexes) as a Catalyst

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

Related Content

Jamison Group – Professor Product Portal

Research in the Jamison group is centered on the development of new reactions and technologies for organic synthesis. Towards these themes, the group has pioneered a number of air-stable nickel precatalysts supported by phosphines and N-heterocyclic carbenes that are readily converted to the active catalyst in situ.

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