[(4-Dimethylaminophenyl)]di(tert-butyl)phosphine
[CAS# 932710-63-9]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: [(4-Dimethylaminophenyl)]di(tert-butyl)phosphine
• Synonyms: N,N-Dimethyl 4-(di(tert-butyl)phosphino)aniline; [4-(Dimethylamino)phenyl]bis(tert-butyl)phosphine
• Molecular Formula: C₁₆H₂₈NP
• Molecular Weight: 265.37
• CAS Registry Number: 932710-63-9
• EC Number: 802-197-6
• SMILES: CC(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C

Properties

• Melting point: 57-61 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H315-H318-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

[(4-Dimethylaminophenyl)]di(tert-butyl)phosphine, commonly known as DABP, was synthesized in the late 20th century during research into sterically hindered phosphine ligands for catalytic applications. The compound combines a dimethylamino group on the benzene ring with two tert-butyl groups attached to the phosphorus atom. The motivation for this discovery was the need for ligands to enhance the performance and stability of transition metal catalysts in various chemical transformations.

The primary application of DABP is as a ligand in transition metal catalysis. Its unique structure, with a combination of an electron-donating dimethylamino group and a tert-butyl group, has excellent steric and electronic properties. This allows it to efficiently form stable complexes with metals such as palladium, platinum, and nickel. These complexes are used in a variety of catalytic processes: DABP is used in Suzuki-Miyaura and Heck reactions, which are essential for the formation of carbon-carbon bonds in organic synthesis. Its bulky tert-butyl group helps minimize unwanted interactions and stabilizes the active metal center to prevent catalyst deactivation. Metal complexes based on DABP are also used in hydrogenations, where they facilitate the addition of hydrogen to unsaturated organic compounds and play an important role in the pharmaceutical and petrochemical industries.

In pharmaceutical synthesis, DABP improves the efficiency of processes used to manufacture active pharmaceutical ingredients (APIs). Its ability to form highly active and selective metal complexes ensures high yield and purity in the synthesis of complex molecules, aiding the development of new drugs and therapies.

DABP is used in materials science to synthesize advanced materials. Its ligands facilitate the preparation of polymers and nanomaterials with controlled structures and properties. For example, DABP-based catalysts are used in polymerization processes to produce materials with specific mechanical and thermal properties, which are valuable for making high-performance plastics and composites.

In coordination chemistry, DABP is a versatile ligand used to study metal-ligand interactions. Its unique structure allows researchers to explore various aspects of coordination chemistry, including bond formation, electronic effects, and catalytic activity. This knowledge is important for designing new catalysts and improving existing catalysts for industrial applications.

The role of DABP extends to environmental applications, particularly in the development of green chemistry catalysts. Its ability to stabilize transition metals enables the design of catalysts that minimize waste and reduce the use of hazardous reagents in chemical processes. This is in line with the principles of sustainable chemistry and promotes the development of environmentally friendly industrial processes.

References

2022. Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes. Synthesis, 54(24).
DOI: 10.1055/s-0041-1737493

2021. Lewis acid-mediated Suzuki-Miyaura cross-coupling reaction. Nature Catalysis, 4(12).
DOI: 10.1038/s41929-021-00719-6

2019. Application of Organometallic Catalysts in API Synthesis. Organometallics in Process Chemistry.
DOI: 10.1007/3418_2019_31