[5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine
[CAS# 877399-00-3]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: [5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine
• Synonyms: [5-Bromo-3-[[(R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]oxy]pyridin-2-yl]amine
• Molecular Formula: C₁₃H₁₀BrCl₂FN₂O
• Molecular Weight: 380.04
• CAS Registry Number: 877399-00-3
• EC Number: 700-798-7
• SMILES: C[C@H](C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)Br)N

Properties

• Density: 1.643

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H317-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P333+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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

[5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine is a compound of considerable interest in the field of medicinal chemistry and chemical research due to its unique structural features and diverse potential applications. This substance is characterized by a pyridine ring substituted with a bromo group and an ethoxy group attached to a dichlorofluorophenyl moiety. The presence of these substituents imparts distinctive chemical properties that make this compound valuable in various contexts.

The discovery of [5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine is a product of ongoing efforts in organic chemistry to explore and develop compounds with specific functional attributes. This particular molecule emerged from research focused on designing novel substances with potential biological and chemical activities. The synthesis of this compound involves the introduction of the bromo and ethoxy groups into the pyridine ring, followed by the attachment of the dichlorofluorophenyl group through a carefully controlled chemical reaction. This multi-step synthesis is a testament to the advances in synthetic chemistry that enable the creation of complex molecules with precision.

One of the primary applications of [5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine is in the development of pharmaceuticals. The unique arrangement of functional groups in this compound makes it a promising candidate for further research into its potential therapeutic effects. Specifically, compounds with similar structures have been investigated for their ability to interact with biological targets, such as enzymes or receptors, which can lead to the development of new drugs. The presence of halogen substituents and an ethoxy group may contribute to the compound's binding affinity and selectivity, enhancing its potential as a drug candidate.

In addition to its pharmaceutical applications, this compound is also explored for its utility in chemical research and development. Its structure allows it to participate in various chemical reactions, making it a valuable intermediate in the synthesis of other complex molecules. The bromine atom, in particular, can be used in cross-coupling reactions, a common technique in organic synthesis that facilitates the formation of carbon-carbon bonds. This property is useful for constructing larger and more intricate molecular structures that may have further applications in materials science or other areas of chemistry.

Furthermore, the compound's potential applications extend to agrochemical formulations. The unique combination of functional groups could provide activity against specific biological pests or pathogens, making it a candidate for investigation in the development of new pesticides or herbicides. The ability to tailor chemical properties through modifications of the substituents on the pyridine ring offers opportunities for creating effective agrochemical agents with improved efficacy and safety profiles.

Overall, [5-Bromo-3-[(1R)-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-yl]amine exemplifies the advancements in chemical synthesis and the exploration of new compounds with diverse applications. Its discovery highlights the continuous efforts in the field of chemistry to develop molecules with specific functionalities that can impact various industries, from pharmaceuticals to agrochemicals.

References

2019. Synthesis of Crizotinib and Etoricoxib. Synfacts, 15(2).
DOI: 10.1055/s-0037-1612025

2014. Crizotinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0283

2011. Synthesis of Crizotinib (PF-02341066). Synfacts, 12(1).
DOI: 10.1055/s-0031-1289313