Di-tert-butylphosphine
[CAS# 819-19-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Di-tert-butylphosphine
• Synonyms: HP(t-Bu)2
• Molecular Formula: C₈H₁₉P
• Molecular Weight: 146.21
• CAS Registry Number: 819-19-2
• EC Number: 628-263-2
• SMILES: CC(C)(C)PC(C)(C)C

Properties

• Melting point: -17 ºC
• Boiling point: 38-40 ºC
• Flash point: -18 ºC

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Hazard Statements: H225-H250-H314
• Precautionary Statements: P210-P222-P231-P233-P240-P241-P242-P243-P264-P280-P301+P330+P331-P302+P334-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P370+P378-P403+P235-P405-P422-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Pyrophoric liquids	Pyr. Liq.	1	H250
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H302
Pyrophoric solids	Pyr. Sol.	1	H250
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

Di-tert-butylphosphine is a prominent organophosphorus compound known for its significant role in organometallic chemistry. This substance, with the chemical formula (C₄H₁₀P), features two tert-butyl groups attached to a central phosphorus atom. Its unique structure imparts both steric bulk and electronic properties that are crucial for its applications as a ligand in various catalytic processes.

The discovery of di-tert-butylphosphine stemmed from the need for ligands that could stabilize metal centers in catalytic reactions. The steric bulk provided by the tert-butyl groups prevents unwanted interactions between the metal center and other reactants or by-products, thereby enhancing the stability and selectivity of the catalyst. This steric protection is particularly valuable in reactions involving bulky substrates or conditions that are prone to catalyst deactivation.

Di-tert-butylphosphine is widely utilized in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are essential in organic synthesis for forming carbon-carbon bonds, which are crucial for the construction of complex organic molecules. The ligand’s ability to stabilize palladium catalysts while preventing side reactions leads to higher yields and better control over reaction outcomes.

In addition to its role in cross-coupling reactions, di-tert-butylphosphine is also employed in other catalytic processes, including hydrogenation and carbonylation reactions. Its unique steric and electronic properties make it a versatile tool for optimizing reaction conditions and improving the efficiency of various catalytic systems.

The development of di-tert-butylphosphine highlights the ongoing advancements in ligand design and its impact on catalytic chemistry. By offering enhanced stability and selectivity, this compound contributes significantly to both academic research and industrial applications, demonstrating the importance of designing ligands with tailored properties to meet the demands of complex chemical reactions.

Overall, di-tert-butylphosphine exemplifies how strategic ligand design can improve catalytic performance, making it a valuable asset in the field of organometallic chemistry.

References

2024. New ferrocene- and ruthenocene-based nickel pincer complexes. Russian Chemical Bulletin, 73(10).
DOI: 10.1007/s11172-024-4399-z

2024. Thermal Decomposition of the Complex [tBu3PH][HB(C6F5)3]. Russian Journal of General Chemistry, 94(14).
DOI: 10.1134/s1070363224140056

2009. Synthesis of new secondary phosphine chalcogenides with bulky substituents from aryl(hetaryl)ethenes, red phosphorus, sulfur, and selenium. Russian Journal of General Chemistry, 79(8).
DOI: 10.1134/s1070363209080052