2-Cyano-5-fluorobenzyl bromide
[CAS# 421552-12-7]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2-Cyano-5-fluorobenzyl bromide
• Synonyms: 2-(Bromomethyl)-4-fluorobenzonitrile
• Molecular Formula: C₈H₅BrFN
• Molecular Weight: 214.03
• CAS Registry Number: 421552-12-7
• EC Number: 675-637-6
• SMILES: C1=CC(=C(C=C1F)CBr)C#N

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H290-H302-H312-H314-H315-H318-H319-H332-H335
• Safety Statements: P234-P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Cyano-5-fluorobenzyl bromide, with the chemical formula C8H4BrFNC, is an important organic compound used in various fields of chemical synthesis and pharmaceuticals. The compound features a benzyl group substituted with a cyano group at the 2-position, a fluorine atom at the 5-position, and a bromine atom, making it a versatile and reactive molecule in organic chemistry.

The discovery and synthesis of 2-cyano-5-fluorobenzyl bromide involve a straightforward process starting from 2-cyano-5-fluorobenzyl alcohol. The alcohol is treated with a brominating agent such as phosphorus tribromide or bromine in the presence of a suitable solvent. This reaction introduces the bromine atom to the benzyl group, converting the alcohol to 2-cyano-5-fluorobenzyl bromide. This compound is highly valued for its reactivity due to the presence of both cyano and bromine functional groups.

In the realm of chemical synthesis, 2-cyano-5-fluorobenzyl bromide is used as an intermediate in the preparation of more complex molecules. Its structure allows for various chemical modifications, making it a valuable reagent for building diverse chemical libraries. The cyano group provides a strong electron-withdrawing effect, which enhances the reactivity of the benzyl bromide group. This property is exploited in coupling reactions and other synthetic transformations to produce compounds with potential applications in different fields.

One significant application of 2-cyano-5-fluorobenzyl bromide is in the pharmaceutical industry. The compound is used as a building block in the synthesis of drugs and biologically active compounds. Its ability to form stable bonds and participate in further chemical reactions makes it an essential intermediate in the development of new pharmaceuticals. Researchers utilize this compound to create novel molecules with potential therapeutic effects, including those targeting cancer, cardiovascular diseases, and neurological disorders.

Additionally, 2-cyano-5-fluorobenzyl bromide is employed in materials science. It is used in the synthesis of functional materials and specialty chemicals. The compound's ability to act as a reactive intermediate makes it useful for designing materials with specific properties, such as those required for electronic or optical applications. Its role in creating advanced materials underscores its importance beyond traditional organic synthesis and pharmaceuticals.

The ongoing research into the applications of 2-cyano-5-fluorobenzyl bromide continues to reveal new uses and potential advancements. Its reactivity and versatility in chemical synthesis make it a valuable compound for scientists working on novel drug development and material innovations. The compound's role in advancing these fields highlights its significance in both academic research and industrial applications.

Overall, 2-cyano-5-fluorobenzyl bromide stands out as a crucial compound in organic synthesis and pharmaceuticals. Its synthesis is straightforward, and its applications span drug development and material science, making it an important reagent and intermediate in various chemical processes.

References

2024. Current trends and future directions for the synthesis and pharmacological applications of 2-(2-cyanopyrrolidin-1-yl)-N-3-hydroxyadamantan-1-yl) acetamide (Gliptins). Medicinal Chemistry Research, 33(6).
DOI: 10.1007/s00044-024-03218-y