2-Bromomethyl-1,3-dioxolane
[CAS# 4360-63-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty aldehyde (containing acetal, hemiacetal)
• Name: 2-Bromomethyl-1,3-dioxolane
• Synonyms: Bromoacetaldehyde ethylene acetal
• Molecular Formula: C₄H₇BrO₂
• Molecular Weight: 167.00
• CAS Registry Number: 4360-63-8
• EC Number: 224-443-6
• SMILES: C1COC(O1)CBr

Properties

• Density: 1.613
• Boiling point: 80-82 °C (27 mmHg)
• Refractive index: 1.481-1.483
• Flash point: 62 °C

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	4	H227

Discovery and Applications

2-Bromomethyl-1,3-dioxolane is a chemical compound with significant utility in organic synthesis and various chemical applications. Its structure comprises a 1,3-dioxolane ring with a bromomethyl group attached, making it an important reagent in the synthesis of more complex organic molecules.

The discovery of 2-bromomethyl-1,3-dioxolane can be traced back to research focused on developing versatile intermediates for organic synthesis. This compound is notable for its ability to undergo a range of chemical reactions due to the presence of both a bromine atom and a dioxolane ring. The bromomethyl group is particularly reactive, allowing for various transformations that are useful in synthetic chemistry.

In organic synthesis, 2-bromomethyl-1,3-dioxolane is employed as an intermediate in the preparation of other chemical compounds. Its reactivity facilitates the introduction of the bromomethyl group into different substrates, leading to the formation of a variety of functionalized products. This ability to act as a bromomethylating agent is valuable for synthesizing compounds with specific properties or functionalities.

The dioxolane ring in 2-bromomethyl-1,3-dioxolane contributes to its role as a protecting group in organic synthesis. Protecting groups are used to shield reactive functional groups during chemical reactions, allowing for selective modification of other parts of the molecule. The dioxolane ring can be cleaved under specific conditions to reveal the desired functional group, making this compound useful in multi-step synthesis processes.

In medicinal chemistry, 2-bromomethyl-1,3-dioxolane has been explored for its potential in the synthesis of bioactive molecules. The bromomethyl group can be used to introduce additional functional groups into drug candidates, potentially enhancing their biological activity or selectivity. This versatility makes it a valuable tool in the development of novel pharmaceuticals.

Furthermore, 2-bromomethyl-1,3-dioxolane finds applications in materials science. The ability to modify polymers and other materials using this compound can lead to the development of materials with enhanced properties, such as increased stability or reactivity. Its role in material synthesis highlights its importance beyond traditional organic chemistry applications.

Overall, 2-bromomethyl-1,3-dioxolane is a versatile chemical substance with significant applications in organic synthesis, medicinal chemistry, and materials science. Its reactivity and functional group compatibility make it a valuable intermediate for the creation of a wide range of chemical products.

References

1974. Synthesis and configuration of 2-halomethyl-1,3-dioxolanes. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 23(10).
DOI: 10.1007/bf00921282

2021. Synthesis and Unexpected Transformation of 5-[(1,3-Dioxolan-2-ylmethyl)sulfanyl]-1H-pyrrol-2-amine into 5-{[2-(2-Hydroxyethoxy)ethenyl]sulfanyl}-1H-pyrrol-2-amine in the Presence of a Superbase. Russian Journal of Organic Chemistry, 57(3).
DOI: 10.1134/s1070428021030246