(6-Amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide
[CAS# 2567457-10-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (6-Amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide
• Synonyms: 5-dimethylphosphoryl-2,3-dihydro-1,4-benzodioxin-6-amine
• Molecular Formula: C₁₀H₁₄NO₃P
• Molecular Weight: 227.20
• CAS Registry Number: 2567457-10-5
• SMILES: CP(=O)(C)C1=C(C=CC2=C1OCCO2)N

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 462.2±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 233.3±28.7 ºC (Calc.)^*
• Index of refraction: 1.554 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

(6-Amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide is a heterocyclic organophosphorus compound featuring a 2,3-dihydrobenzo[b][1,4]dioxin core substituted with an amino group at the 6-position and a dimethylphosphine oxide moiety at the 5-position. The bicyclic 1,4-dioxin ring fused to a benzene ring provides structural rigidity and electron-rich character, while the dimethylphosphine oxide group contributes both polarity and reactivity. Such compounds are of interest in synthetic organic chemistry due to the combination of functional groups, which enables multiple pathways for further derivatization.

The synthesis of (6-amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide typically involves selective functionalization of the dihydrobenzo-dioxin precursor. Introduction of the dimethylphosphine oxide group is often achieved through nucleophilic substitution or transition-metal-catalyzed coupling reactions, while the amino group can be introduced via reduction of a nitro precursor or through direct amination reactions. Reaction conditions are carefully optimized to maintain the integrity of the heterocyclic core and prevent side reactions. The product is usually isolated as a crystalline solid and purified by chromatography or recrystallization.

In synthetic chemistry, this compound serves as a versatile intermediate for the preparation of phosphine oxide derivatives, heterocyclic frameworks, and functionalized aromatic compounds. The amino group can engage in acylation, sulfonylation, or condensation reactions, while the phosphine oxide provides a handle for further transformations, including P–C bond formation or complexation with metal centers. This multifunctionality allows stepwise construction of more complex molecules for applications in medicinal or materials chemistry.

In medicinal chemistry, derivatives of this compound are explored for their potential as enzyme inhibitors, receptor ligands, or bioactive heterocycles. The amino group facilitates hydrogen bonding interactions, while the phosphine oxide can enhance polarity and contribute to coordination with biological macromolecules. The rigid fused heterocyclic system provides a scaffold that allows precise spatial orientation of substituents, which is advantageous in drug design and structure–activity relationship studies.

The compound is also relevant in chemical methodology research. Its combination of a heterocyclic core, amino functionality, and phosphine oxide group allows chemists to investigate selective functionalization reactions, protective group strategies, and phosphorus chemistry in a fused-ring context. It can be used to explore new synthetic routes to phosphorus-containing heterocycles and functionalized aromatic compounds with applications in catalysis or materials science.

Physically, (6-amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide is generally obtained as a solid with moderate solubility in polar organic solvents such as dimethylformamide, ethanol, and dichloromethane. It is stable under standard laboratory conditions but should be stored away from strong oxidizing agents or acidic conditions that could affect the amino or phosphine oxide functionality. Proper storage ensures chemical integrity for synthetic, medicinal, and exploratory applications.

Overall, (6-amino-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)dimethylphosphine oxide is a multifunctional heterocyclic organophosphorus compound combining an amino-substituted dihydrobenzo-dioxin scaffold with a dimethylphosphine oxide group. Its structural features enable selective chemical transformations, derivatization, and incorporation into complex molecules, making it a valuable intermediate in synthetic chemistry, medicinal chemistry, and functional material development.

References

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URL: WO-2022268229-A1

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2021. New EGFR degrader. World Intellectual Property Organization.
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