289-68-9

Basic information

• Product Name: Phosphorine
• Synonyms: Phosphate-binding proteolipid; Phosphabenzene; Phosphinine; Phosphoridine; lambda3-Phosphorin; Phosphorin
• CAS NO: 289-68-9
• Molecular Formula: C₅H₅P
• Molecular Weight: 96.067
• Mol File: 289-68-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Phosphorine(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphorine(289-68-9)
• EPA Substance Registry System: Phosphorine(289-68-9)

Safety Data

• Hazardous Substances Data: 289-68-9(Hazardous Substances Data)

Usage

Description

Phosphorine, also known as tetrahydrothiophene oxide, is an organic compound with the molecular formula C4H9OP. It is a colorless liquid that is relatively stable at room temperature and can be easily synthesized from readily available starting materials. Phosphorine is a versatile compound with various industrial and scientific applications.

Uses

Used in Pharmaceutical Industry:
Phosphorine is used as a reagent in organic synthesis processes for the production of pharmaceuticals. It serves as an intermediate in the synthesis of various drugs, contributing to the development of new medications.
Used in Agrochemical Industry:
Phosphorine is also utilized as an intermediate in the production of agrochemicals, playing a role in the creation of pesticides and other agricultural products to enhance crop protection and yield.
Used in Organic Optoelectronics:
Due to its unique chemical and physical properties, Phosphorine has potential applications in the field of organic optoelectronics. It can be employed in the development of advanced materials for use in electronic devices and systems.

Upstream product

• 153184-95-3 vinyldiallylphosphine 
• 158276-78-9 2-(trimethylsilyl)-λ³-phosphinine 
• 1315511-37-5 N1,N1,N1,N1-tetramethyl-1λ5-phosphinine-1,1-diamine 
• 32323-37-8 1,1-dimethoxyphosphinine 
• 24442-69-1 malononitrile 
• 189098-86-0 P-(diallyl)-N-(diisopropyl)aminophosphine 
• 16523-89-0 triallylphosphine 
• 31732-31-7 1,1-dibutyl-1-stannacyclohexa-2,5-diene 
• 7789-60-8 phosphorus tribromide 

Relevant articles and documents

2-(Trimethylsilyl)-λ3-Phosphinine: Synthesis, Coordination Chemistry, and Reactivity

The [4+2] cycloaddition reaction between 2-pyrone and Me3Si?C≡P gives the corresponding 2-(trimethylsilyl)-λ3-phosphinine in good yields as a rather air and moisture stable, colorless oil. Insight into the regioselectivity of the pericyclic reaction was obtained with the help of deuterium-labeling experiments. The silyl-phosphinine acts as a ligand for the preparation of a Cu(I) and the first crystallographically characterized phosphinine-Ag(I) complex. The title compound was further used as a starting material for an alternative preparation of the parent phosphinine C5H5P by means of protodesilylation with HCl. C5H5P reacts with CuBr?S(CH3)2 to give an infinite Cu(I)Br coordination polymer. DFT calculations shed light on the influence of the -Si(CH3)3 group on the electronic properties of the aromatic phosphorus heterocycle.

Reduction of λ5-Phosphinines

A convenient method to easily prepare parent λ3-phosphinine from easily accessible λ5-precursors was developed. A series of λ5-phosphinines bearing heteroatom substituents OMe, SMe, and/or NMe2 at the phosphorus

Synthesis of the Parent Phosphinine and Phosphaalkyne by Flash Thermolysis of Vinyldiallyl- and Triallyl-phosphine

The parent phosphinine is obtained in ca. 40percent yield by thermolysis of vinyldiallylphosphine at 700 deg C at 10-3 Torr; under the same conditions, triallylphosphine mainly yields HCP which can be purified by trap-to-trap distillation.