Skip to Content
Merck
All Photos(1)

Key Documents

799718

Sigma-Aldrich

AlPhos

Synonym(s):

Di-1-adamantyl(4″-butyl-2″,3″,5″,6″-tetrafluoro-2′,4′,6′-triisopropyl-2-methoxy-meta-terphenyl)phosphine

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C52H67F4OP
CAS Number:
Molecular Weight:
815.06
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Assay

≥95%

Quality Level

form

powder

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

mp

218-223 °C

functional group

phosphine

storage temp.

−20°C

InChI

1S/C52H67F4OP/c1-9-10-12-38-46(53)48(55)45(49(56)47(38)54)44-40(29(4)5)21-39(28(2)3)43(42(44)30(6)7)37-13-11-14-41(57-8)50(37)58(51-22-31-15-32(23-51)17-33(16-31)24-51)52-25-34-18-35(26-52)20-36(19-34)27-52/h11,13-14,21,28-36H,9-10,12,15-20,22-27H2,1-8H3/t31-,32+,33?,34-,35+,36?,51+,52?,58?

InChI key

ALWIRDZSIXWCBO-VABCSHEKSA-N

Application

AlPhos is a biaryl monophosphine ligand that can be used:
  • In the Pd-catalyzed Buchwald-Hartwig cross-coupling reactions.
  • To synthesize highly regioselective aryl fluorides by Pd-catalyzed fluorination of a variety of activated aryl and heteroaryl triflates and bromides.
  • To prepare aryl thioethers by C–S cross-coupling of thiols with aromatic electrophile in the presence of palladium catalyst.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

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.

Already Own This Product?

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

Visit the Document Library

A fluorinated ligand enables room-temperature and regioselective Pd-catalyzed fluorination of aryl triflates and bromides
Sather AC, et al.
Journal of the American Chemical Society, 137(41), 13433-13438 (2015)
In-depth assessment of the palladium-catalyzed fluorination of five-membered heteroaryl bromides
Milner PJ, et al.
Organometallics, 34(19), 4775-4780 (2015)
Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases
Xu Jessica, et al.
ACS Catalysis, 9(7), 6461-6466 (2019)
Development of Palladium Precatalysts that Efficiently Generate LPd (0) Active Species
Shaughnessy KH
Israel Journal of Chemistry, 60(3-4), 180-194 (2020)

Articles

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

Related Content

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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