2-(Dimethylphosphinyl)benzenamine
[CAS# 1197953-47-1]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 2-(Dimethylphosphinyl)benzenamine
• Synonyms: (2-Aminophenyl)dimethylphosphine oxide
• Molecular Formula: C₈H₁₂NOP
• Molecular Weight: 169.16
• CAS Registry Number: 1197953-47-1
• EC Number: 692-109-0
• SMILES: CP(=O)(C)C1=CC=CC=C1N

Properties

• Solubility: Soluble (71 g/L) (25 °C), Calc.^*
• Density: 1.11±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.521, Calc.^*
• Boiling Point: 367.5±34.0 °C (760 mmHg), Calc.^*
• Flash Point: 176.1±25.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H315-H319-H332-H334-H335
• Safety Statements: P233-P260-P261-P264-P264+P265-P270-P271-P280-P284-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Respiratory sensitization	Resp. Sens.	1	H334
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-(Dimethylphosphinyl)benzenamine is an organophosphorus compound that was discovered during research focused on developing new chemical intermediates for pharmaceuticals and agrochemicals. The compound was synthesized through a series of reactions involving the introduction of a dimethylphosphinyl group to a benzenamine structure. This discovery was part of broader efforts in the 20th century to explore the chemical properties and potential applications of organophosphorus compounds. These compounds are known for their unique reactivity and ability to act as ligands or intermediates in various chemical reactions.

2-(Dimethylphosphinyl)benzenamine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its structure allows it to participate in reactions that form complex molecules with potential therapeutic properties. The phosphinyl group can enhance the binding affinity and specificity of drug molecules to their target enzymes, making it useful in designing enzyme inhibitors that can treat diseases like cancer and neurodegenerative disorders.

In agrochemical research, 2-(Dimethylphosphinyl)benzenamine is used to synthesize new herbicides and pesticides. The phosphinyl group improves the efficacy and stability of these compounds, leading to more effective pest control solutions. Its derivatives can also be used to develop fungicides that protect crops from fungal infections, thereby enhancing agricultural productivity.

The phosphinyl group in 2-(Dimethylphosphinyl)benzenamine makes it an effective ligand in transition metal catalysis. It can facilitate various catalytic reactions, including cross-coupling and polymerization, which are essential in industrial chemical processes. This compound serves as a reagent in organic synthesis, participating in reactions that form carbon-phosphorus bonds. These reactions are crucial for creating organophosphorus compounds with diverse chemical functionalities.

In materials science, 2-(Dimethylphosphinyl)benzenamine can be used to synthesize polymers with unique properties. The incorporation of the phosphinyl group can enhance the thermal stability, flame retardancy, and mechanical properties of these polymers, making them suitable for advanced applications in electronics, automotive, and aerospace industries. The compound is also used in developing advanced materials that require specific chemical and physical properties, such as high-performance coatings and adhesives.

References

2017. Brigatinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0179