(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide
[CAS# 52509-14-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphorus halide
• Name: (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide
• Synonyms: 1,3-dioxolan-2-ylmethyl(triphenyl)phosphanium;bromide
• Molecular Formula: C₂₂H₂₂O₂P.Br
• Molecular Weight: 429.29
• CAS Registry Number: 52509-14-5
• EC Number: 257-977-3
• SMILES: C1COC(O1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]

Properties

• Melting point: 193-195 °C (Expl.)

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide, also known by its chemical formula C₁₈H₁₉BrO₂P, is an organic compound consisting of a triphenylphosphonium cation (C₆H₅)₃P, a bromide anion (Br^-), and a 1,3-dioxolane-2-ylmethyl group attached to the phosphorus atom. The 1,3-dioxolane group is a heterocyclic structure consisting of an oxygen atom and a two-carbon chain, which is bound to a methylene (-CH₂) group that links it to the triphenylphosphonium cation.

This compound has found utility primarily as a reagent in organic synthesis, particularly in reactions where the triphenylphosphonium group plays a role as a leaving group or in the formation of intermediates in various chemical processes. The structure of (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide makes it useful for specific types of reactions, including nucleophilic substitution reactions, and in the preparation of phosphonium salts that can be further manipulated to produce more complex organic compounds.

In the context of synthetic chemistry, phosphonium salts such as (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide are commonly used in the synthesis of various organophosphorus compounds. These compounds are important in a variety of applications, ranging from catalysis in organic reactions to use as intermediates in the production of more specialized chemicals. The 1,3-dioxolane group, being a cyclic ether, is a relatively stable functional group that can be easily incorporated into larger molecules, making this compound valuable for the construction of complex molecular architectures.

One of the notable areas where this compound may be applied is in the development of chemical intermediates for pharmaceutical and agricultural chemicals. By providing a route to highly functionalized organic compounds, it contributes to the design of bioactive molecules and molecular tools. However, its specific role and further applications within these fields are often determined by the particular synthetic pathways it enables.

Overall, (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide serves primarily as a reagent in organic synthesis and chemical research, with its properties facilitating the formation of phosphonium-based intermediates. This has made it a useful tool in the creation of complex organic molecules with diverse functional groups, though it remains most significant in laboratory-scale synthesis and chemical process development.

References

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