Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

901166

Sigma-Aldrich

cis-[2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl](2-methylphenyl)nickel(II) chloride

Synonym(s):

cis-((S)-BINAP)Ni(o-tolyl)Cl

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

About This Item

Empirical Formula (Hill Notation):
C51H39ClNiP2
CAS Number:
1594113-05-9
Molecular Weight:
807.95
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or solid

Quality Level

100

reaction suitability

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

mp

>300 °C

SMILES string

Cl[Ni]1(P(C2=C([H])C([H])=C([H])C([H])=C2[H])(C3=C([H])C([H])=C([H])C([H])=C3[H])C(C([H])=C4[H])=[C@@]([C@@]5=C(P1(C6=C([H])C([H])=C([H])C([H])=C6[H])C7=C([H])C([H])=C([H])C([H])=C7[H])C([H])=C([H])C8=C5C([H])=C([H])C([H])=C8[H])C9=C4C([H])=C([H])C([H])=C

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 Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

901166-100MG:
901166-VAR:
901166-BULK:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCF3673

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

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.

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