2,4-Difluorobenzylamine
[CAS# 72235-52-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: 2,4-Difluorobenzylamine
• Molecular Formula: C₇H₇F₂N
• Molecular Weight: 143.13
• CAS Registry Number: 72235-52-0
• EC Number: 276-502-0
• SMILES: C1=CC(=C(C=C1F)F)CN

Properties

• Density: 1.204
• Boiling point: 82-84 °C (15 mmHg)
• Refractive index: 1.49-1.493
• Boiling point: 55-57 °C
• Flash point: 68 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 2735

Discovery and Applications

2,4-Difluorobenzylamine, a fluorinated aromatic amine, was discovered through synthetic organic chemistry research aimed at developing novel compounds with unique chemical properties. Chemists sought to introduce fluorine atoms into aromatic amine molecules to modulate their reactivity and physicochemical characteristics. Through synthetic routes involving selective fluorination reactions, 2,4-Difluorobenzylamine was successfully synthesized and characterized. Its discovery represented a significant advancement in the field of fluorine chemistry, offering a new building block for the synthesis of diverse organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

2,4-Difluorobenzylamine serves as a key intermediate in the synthesis of pharmaceutical compounds, including fluorinated drugs and bioactive molecules. Its fluorinated moiety enhances the metabolic stability, lipophilicity, and binding affinity of drug candidates, contributing to improved pharmacokinetic properties and therapeutic efficacy. 2,4-Difluorobenzylamine derivatives are utilized as building blocks for the synthesis of fluorinated heterocycles and drug-like scaffolds. These compounds are valuable tools for medicinal chemists in the design and optimization of drug candidates with enhanced potency, selectivity, and metabolic stability.

2,4-Difluorobenzylamine derivatives are employed in the synthesis of fluorinated pesticides and herbicides. These compounds exhibit enhanced efficacy and environmental persistence compared to their non-fluorinated counterparts, making them valuable components of modern agricultural chemical formulations.

2,4-Difluorobenzylamine derivatives are utilized in the synthesis of fluorinated polymers and materials with tailored properties for specific applications. Their fluorinated moieties impart hydrophobicity, thermal stability, and chemical resistance to polymers, making them suitable for coatings, membranes, and electronic devices.

2,4-Difluorobenzylamine serves as a versatile starting material for the synthesis of fluorine-containing reagents and organofluorine compounds. Its fluorinated benzylamine backbone enables the introduction of fluorine atoms into organic molecules through various synthetic transformations, including nucleophilic substitution, metal-catalyzed fluorination, and electrophilic fluorination reactions.

2,4-Difluorobenzylamine derivatives are utilized as fluorine NMR probes in chemical and biological research. Their unique chemical shifts and sensitivity to environmental changes make them valuable tools for studying molecular structure, dynamics, and interactions in complex systems.

References

2022. Practical and Efficient Route to Dolutegravir Sodium via One-Pot Synthesis of Key Intermediate with Controlled Formation of Impurities. Russian Journal of Organic Chemistry, 58(4).
DOI: 10.1134/s1070428022040091

2021. Gram-Scale Synthesis of Dolutegravir Sodium. Synfacts, 17(12).
DOI: 10.1055/s-0040-1720914

2016. Development of Synthetic Routes to Dolutegravir. Synthesis of Heterocycles in Contemporary Medicinal Chemistry.
DOI: 10.1007/7081_2016_200