Di-tert-butylchlorophosphane
[CAS# 13716-10-4]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Di-tert-butylchlorophosphane
• Synonyms: Bis(1,1-dimethylethyl)-phosphinous chloride
• Molecular Formula: C₈H₁₈ClP
• Molecular Weight: 180.66
• CAS Registry Number: 13716-10-4
• EC Number: 604-003-3
• SMILES: CC(C)(C)P(C(C)(C)C)Cl

Properties

• Density: 0.95
• Melting point: 2-3 ºC
• Boiling point: 48 ºC (3 mmHg)
• Refractive index: 1.48-1.483
• Flash point: 61 ºC

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Flammable liquids	Flam. Liq.	4	H227

• Transport Information: UN 3265

Discovory and Applicatios

Di-tert-butylchlorophosphane is an organophosphorus compound that has gained attention due to its utility in organic synthesis and materials science. The compound consists of a phosphorus atom bonded to two tert-butyl groups and a chlorine atom, giving it the chemical formula (C₄H₉)₂PCl. This structure provides a combination of steric bulk from the tert-butyl groups and reactivity from the chlorine atom, making it a valuable reagent in various chemical transformations.

The discovery of Di-tert-butylchlorophosphane is part of the broader development of organophosphorus chemistry, which has been essential for advancing synthetic methodologies. Phosphorus compounds, particularly those containing chlorine, have long been used as intermediates in the preparation of more complex phosphorus-based ligands and reagents. The introduction of the tert-butyl groups in Di-tert-butylchlorophosphane was specifically aimed at creating a reagent that could offer both reactivity and control in subsequent reactions.

In organic synthesis, Di-tert-butylchlorophosphane is primarily used as a precursor to other organophosphorus compounds. It is particularly useful in the synthesis of phosphine ligands, which are essential in catalysis. The bulky tert-butyl groups help to create ligands that provide steric protection around the metal center in catalytic complexes, enhancing the selectivity and efficiency of catalytic reactions. This is crucial in processes such as cross-coupling reactions, where the control of reaction pathways can lead to higher yields and fewer side products.

Moreover, the chlorine atom in Di-tert-butylchlorophosphane is highly reactive and can be easily replaced with various nucleophiles, making it a versatile building block for the preparation of a wide range of phosphorus-containing compounds. This reactivity is exploited in the synthesis of phosphine oxides, phosphonates, and other derivatives that have applications in both organic synthesis and materials science.

In materials science, Di-tert-butylchlorophosphane is utilized in the creation of novel materials with unique electronic and optical properties. Its derivatives are involved in the development of flame retardants, plasticizers, and stabilizers for polymers, contributing to the improvement of material performance in various industrial applications.

The compound is also of interest in academic research, particularly in the study of phosphorus chemistry and the development of new synthetic methods. Researchers use Di-tert-butylchlorophosphane to explore the effects of steric and electronic factors on the reactivity of phosphorus compounds, providing insights that can lead to the design of more effective reagents and catalysts.

In summary, Di-tert-butylchlorophosphane is a valuable reagent in both organic synthesis and materials science, known for its reactivity and the steric protection offered by its tert-butyl groups. Its discovery has paved the way for the development of a wide range of organophosphorus compounds and advanced materials, making it a significant compound in modern chemistry.

References

2003. C8H18ClP, Di-t-butylchlorophosphine. Molecules Containing Five or More Carbon Atoms.
DOI: 10.1007/10735542_722

1975. Synthesis of m- and p-di-tert-butylphosphinobenzoic acids and some of their derivatives. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 24(1).
DOI: 10.1007/bf00926319

1976. Conformations of certain dialkylarylphosphines and their oxides. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 25(10).
DOI: 10.1007/bf02659523