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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:
1237588-12-3
Molecular Weight:
463.63
MDL number:
MFCD17018759
UNSPSC Code:
12352005
PubChem Substance ID:
329766227
NACRES:
NA.22

Quality Level

100

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.

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)
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)
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)

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

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