Cyclohexyl di-tert-butylphosphine
[CAS# 436865-11-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Cyclohexyl di-tert-butylphosphine
• Synonyms: Di-tert-butylcyclohexylphosphine
• Molecular Formula: C₁₄H₂₉P
• Molecular Weight: 228.35
• CAS Registry Number: 436865-11-1
• EC Number: 630-596-3
• SMILES: CC(C)(C)P(C1CCCCC1)C(C)(C)C

Properties

• Boiling point: 282 ºC
• Flash point: 129 ºC

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

Cyclohexyl di-tert-butylphosphine is a notable organophosphorus compound recognized for its unique chemical properties and applications in various fields of chemistry. This substance, characterized by its cyclohexyl and di-tert-butylphosphine groups, is primarily employed as a ligand in catalytic processes and other synthetic applications.

The discovery of Cyclohexyl di-tert-butylphosphine emerged from the ongoing exploration of phosphine ligands with tailored steric and electronic properties. The synthesis of this compound involves the reaction of cyclohexylphosphine with tert-butyl groups, typically achieved through a process of alkylation. This reaction is conducted under controlled conditions to ensure high purity and yield. Characterization of Cyclohexyl di-tert-butylphosphine is performed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry to confirm its structure and verify its purity.

In the realm of catalysis, Cyclohexyl di-tert-butylphosphine is used as a ligand in various metal-catalyzed reactions. Its unique structure, with bulky tert-butyl groups and a cyclohexyl ring, imparts specific steric and electronic properties that enhance the performance of metal catalysts. This compound is particularly effective in facilitating reactions such as cross-coupling, hydrogenation, and carbonylation. The steric hindrance provided by the tert-butyl groups can improve selectivity and activity in these reactions, making Cyclohexyl di-tert-butylphosphine a valuable tool in synthetic chemistry.

Additionally, the compound finds applications in materials science, where its ability to stabilize metal centers contributes to the development of advanced materials. For instance, Cyclohexyl di-tert-butylphosphine can be used in the synthesis of functionalized polymers and materials with specific electronic or optical properties. The versatility of this compound allows for the creation of materials with enhanced performance in various industrial applications, including electronics and coatings.

Cyclohexyl di-tert-butylphosphine also plays a role in research and development, where its properties are leveraged to design new catalytic systems and explore novel synthetic methodologies. The compound's effectiveness in coordinating with metal centers and influencing reaction pathways makes it a valuable asset in advancing chemical science.

Handling and storage of Cyclohexyl di-tert-butylphosphine require standard precautions due to its chemical reactivity. The compound should be kept in a dry, cool environment, protected from moisture and air to maintain its stability and effectiveness.

Future research on Cyclohexyl di-tert-butylphosphine may focus on expanding its applications and optimizing its use in various catalytic and materials science contexts. Investigations into its properties and performance could lead to new advancements in synthetic chemistry and material development.