PMC2012

MorDalPhos

≥98%, ISOM8^™

• Synonym(s): MorDalphos, Di(1-adamantyl)-2-morpholinophenylphosphine, Mor-DalPhos
• Empirical Formula (Hill Notation): C₃₀H₄₂NOP
• CAS Number: 1237588-12-3
• Molecular Weight: 463.63
• UNSPSC Code: 12352005
• MDL number: MFCD17018759

Properties

• product line: ISOM8^™
• Quality Segment: 300
• 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

Description

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

Safety Information

• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable