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751618

Sigma-Aldrich

MorDalphos

97%

Synonym(s):
Di(1-adamantyl)-2-morpholinophenylphosphine
Empirical Formula (Hill Notation):
C30H42NOP
CAS Number:
Molecular Weight:
463.63
MDL number:
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.

Packaging

250 mg in glass bottle
1, 5 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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)
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)
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

DalPhos is air-stable and contains the bulky di(1-adamantyl)phosphino [P(1-Ad)2] fragment. These ligands are useful in Pd-catalyzed C-N and C-C bond formation. Both Me-DalPhos and Mor-DalPhos allow for Pd-catalyzed ammonia, hydrazine and acetone cross-coupling with good functional group tolerance

Related Content

Stradiotto Group – Professor Product Portal

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.

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