4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide
[CAS# 707-61-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide
• Synonyms: 1-Phenyl-3-methyl-1-oxo-3-phospholine
• Molecular Formula: C₁₁H₁₃OP
• Molecular Weight: 192.19
• CAS Registry Number: 707-61-9
• EC Number: 211-901-5
• SMILES: CC1=CP(=O)(CC1)C2=CC=CC=C2

Properties

• Melting point: 64 °C
• Boiling point: 150 °C (0.15 mmHg)
• Refractive index: 1.5707
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335-H351-H411
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Carcinogenicity	Carc.	2	H351
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

4,5-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide is a notable chemical compound with significant applications in organic chemistry and materials science. This compound features a phosphole ring with a distinctive 4,5-dihydro structure, along with a methyl and phenyl group, and an oxide functionality. Its unique structure imparts valuable properties that make it useful in various chemical contexts.

The discovery of 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide can be traced back to ongoing research into phosphole derivatives, which are less commonly studied compared to their analogs such as phosphines and phosphine oxides. The phosphole ring, a five-membered aromatic ring containing a phosphorus atom, is known for its electron-rich nature and unique reactivity. The introduction of a 4,5-dihydro substitution pattern in the phosphole ring significantly impacts the compound's electronic and steric properties.

The synthesis of 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide typically involves the formation of the phosphole ring followed by the introduction of the methyl and phenyl groups. The oxidation of the phosphole ring to form the 1-oxide is a crucial step, which enhances the compound's stability and modifies its reactivity. Various synthetic methods can be employed to achieve these modifications, including cyclization reactions and selective oxidation processes.

In terms of applications, 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide is used primarily in the development of advanced materials and as a reagent in organic synthesis. The phosphole ring, due to its electron-rich nature, can act as a ligand in coordination chemistry. This makes 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide valuable in the preparation of metal complexes with potential applications in catalysis and material science.

One of the key applications of 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide is as a ligand in transition metal catalysis. The phosphole ring's ability to coordinate with metal centers allows for the formation of complexes that can be used in various catalytic processes. These processes include hydrogenation, cross-coupling reactions, and other transformations that are essential in organic synthesis and industrial chemistry.

Additionally, the compound is explored for its potential use in the development of new materials. The presence of the phosphole ring and the 1-oxide functionality can impart unique electronic and optical properties to materials. This makes 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide an interesting candidate for applications in organic semiconductors, light-emitting devices, and other advanced materials.

The compound's utility in organic synthesis is also notable. It can serve as a versatile reagent in various transformations, including nucleophilic substitution and addition reactions. The 1-oxide functionality can influence the reactivity of the phosphole ring, allowing for selective functionalization and modification of the compound in synthetic applications.

Moreover, research into 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide contributes to a deeper understanding of phosphole chemistry and its potential applications. The compound's unique structural features and reactivity profile make it a valuable subject of study for chemists interested in exploring new reactions, materials, and applications.

In summary, 4,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide is a significant compound in organic chemistry and materials science. Its distinctive phosphole ring structure, combined with the methyl, phenyl, and 1-oxide groups, imparts valuable properties that make it useful in various applications. From its role as a ligand in metal catalysis to its potential in advanced materials and organic synthesis, this compound continues to be a subject of interest for researchers and practitioners in these fields.

References

2010. Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars. Bioorganic & Medicinal Chemistry Letters, 20(19).
DOI: 10.1016/j.bmcl.2010.01.061

2009. Development and pharmacologic characterization of deoxybromophospha sugar derivatives with antileukemic activity. Investigational New Drugs, 27(5).
DOI: 10.1007/s10637-009-9255-3

2007. Preparation, Structure, and Biological Properties of Phosphorus Heterocycles with a C-P Ring System. Topics in Heterocyclic Chemistry, 10.
DOI: 10.1007/7081_2007_086