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PMC2012

MorDalPhos

≥98%, ISOM8™

Synonym(s):

MorDalphos, Di(1-adamantyl)-2-morpholinophenylphosphine, Mor-DalPhos

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About This Item

Empirical Formula (Hill Notation):
C30H42NOP
CAS Number:
1237588-12-3
Molecular Weight:
463.63
UNSPSC Code:
12352005
MDL number:
MFCD17018759
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product line

ISOM8™

Quality Segment

assay

≥98%

form

solid

purified by

HPLC

reaction suitability

reagent type: ligand, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Coupling Reactions

mp

219-224 °C

application(s)

diagnostic assay manufacturing
life science and biopharma

functional group

phosphine

storage temp.

room temp

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

General description

Welcome to our ISOM8™ line of high-quality products available and able to scale for manufacturing. Within our ISOM8 team, we have expertise and documentation to support ISO 9001 industrial and non-GMP pharma production needs, as defined by our M-Clarity™ Program. Our portfolio of ISOM8 products and chemistries is ever evolving to support our valued Sigma-Aldrich® customers′ requirements. Please navigate to our documents section to look at quality documentation for this product, provided with support of our Elevate Program.

Application

MorDalPhos is an electron-rich, sterically hindered P,N-heterobidentate ligand bridging monophosphines and bisphosphines. It excels in Pd-catalyzed C–N and C–C bond-forming reactions, including Buchwald-Hartwig amination and ammonia monoarylation, with broad functional group tolerance.





Notable Characteristics & Key Uses


  • P,N-Heterobidentate Design: Features a bulky adamantyl-phosphine group paired with a morpholine-containing nitrogen donor, providing a “middle ground” between traditional monophosphines and chelating bisphosphines.
  • High Chemoselectivity: Highly active in chemoselective C–N bond formations, successfully differentiating between closely related amines.
  • Mild Reaction Conditions: Enables reactions to occur under lower catalyst loadings, shorter timeframes, and sometimes under solvent-free or aqueous conditions.
  • Ammonia Monoarylation: Excels in the direct monoarylation of ammonia with aryl chlorides and tosylates — a process historically known to be exceptionally difficult.
  • Heterocycle & Pharmaceutical Synthesis: Frequently applied in the construction of APIs such as MALT1 inhibitors, CNS therapeutics, and anti-inflammatory compounds.
  • Hydrazine & Alkyne Reactions: Used for the monoarylation of hydrazine, acetone derivatives, and in alkyne hydroamination.
  • Functional Group Tolerance: MorDalPhos enables Pd-catalyzed C–N and C–C bond formation with good functional group tolerance, making it highly versatile across diverse synthetic contexts.

Recent Studies and Innovations


  1. Solvent-free amination coupling reactions: MorDalPhos is the enabling ligand for a practical, broad-scope Pd-catalyzed amination platform for triaryl phosphates, with good functional-group tolerance and solvent-free applicability (Zicong Chen et al., 2019).
  2. High Selectivity in Mono-α-Arylation: A highly reactive catalyst system comprising [Pd(2-butenyl)Cl]₂ and MorDalPhos achieves successful mono-α-arylation of aryl and heteroaryl ketones with aryl phosphates. (Xiangmeng Chen et al., 2019).
  3. Ammonia Monoarylation at Room Temperature: MorDalPhos enables selective monoarylation of ammonia, achieving >90% conversion and 76% GC yield of aniline. (Alsabeh et al., 2013).

Legal Information

ISOM8 is a trademark of Sigma-Aldrich Co. LLC
M-CLARITY is a trademark of Merck KGaA, Darmstadt, Germany
SIGMA-ALDRICH is a registered trademark of Merck KGaA, Darmstadt, Germany

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Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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