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751618

Sigma-Aldrich

MorDalphos

97%

Synonym(s):

Di(1-adamantyl)-2-morpholinophenylphosphine

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About This Item

Empirical Formula (Hill Notation):
C30H42NOP
CAS Number:
Molecular Weight:
463.63
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: Arylations

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

mp

219-224 °C

functional group

phosphine

storage temp.

2-8°C

SMILES string

C1CN(CCO1)c2ccccc2P([C@@]34C[C@@H]5C[C@@H](C[C@@H](C5)C3)C4)[C@@]67C[C@@H]8C[C@@H](C[C@@H](C8)C6)C7

InChI

1S/C30H42NOP/c1-2-4-28(27(3-1)31-5-7-32-8-6-31)33(29-15-21-9-22(16-29)11-23(10-21)17-29)30-18-24-12-25(19-30)14-26(13-24)20-30/h1-4,21-26H,5-20H2/t21-,22+,23-,24-,25+,26-,29-,30-

InChI key

CCBRRSUORFMQCZ-BVIFAWIJSA-N

Application

MorDalphos is an electronically rich, sterically hindered P,N-based ancillary ligand developed by the Stradiotto group that can be used in the Buchwald-Hartwig Amination reaction, alkyne hydroamination and monoarylation of compounds such as ammonia, hydrazine, and acetone.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Palladium-catalyzed mono-?-arylation of acetone with aryl halides and tosylates.
Hesp K D, et al.
Journal of the American Chemical Society, 133(14), 5194-5197 (2011)
Stereo-and regioselective gold-catalyzed hydroamination of internal alkynes with dialkylamines.
Hesp K D, et al.
Journal of the American Chemical Society, 132(51), 18026-18029 (2010)
Rational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald?Hartwig Amination of (Hetero) Aryl Chlorides Employing Mor-DalPhos.
Tardiff B, et al.
The Journal of Organic Chemistry, 77(2), 1056-1071 (2011)
AP, N?Ligand for Palladium?Catalyzed Ammonia Arylation: Coupling of Deactivated Aryl Chlorides, Chemoselective Arylations, and Room Temperature Reactions
Lundgren R J, et al.
Angewandte Chemie (International Edition in English), 122(24), 4165-4168 (2010)

Articles

DalPhos ligands enable Pd-catalyzed C-N and C-C bond formation with good functional group tolerance.

DalPhos ligands enable Pd-catalyzed C-N and C-C bond formation with good functional group tolerance.

DalPhos ligands enable Pd-catalyzed C-N and C-C bond formation with good functional group tolerance.

DalPhos ligands enable Pd-catalyzed C-N and C-C bond formation with good functional group tolerance.

Related Content

The main focus of the Stradiotto group has centered on the development and application of novel electronically rich, sterically encumbered P,N-based ancillary ligands for use in late metal catalysis, including Pd and Au chemistry.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

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