N-[5-Chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamic acid 1,1-dimethylethyl ester
[CAS# 1269440-69-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: N-[5-Chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamic acid 1,1-dimethylethyl ester
• Synonyms: tert-butyl N-[5-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
• Molecular Formula: C₁₇H₂₄BClFNO₄
• Molecular Weight: 371.64
• CAS Registry Number: 1269440-69-8
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2F)NC(=O)OC(C)(C)C)Cl

Properties

• Density: 1.18±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.507, Calc.^*
• Boiling Point: 404.9±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 198.7±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-[5-Chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamic acid 1,1-dimethylethyl ester is a boronic acid ester derivative widely recognized for its role as an intermediate in the synthesis of pharmaceutical agents. This compound exemplifies the versatility of boron-based chemistry, which has become indispensable in the development of new drugs and agrochemicals. The structure incorporates a boronate functional group, facilitating cross-coupling reactions essential for forming carbon-carbon bonds.

The discovery of this compound is rooted in the search for novel arylboronates that enhance the efficacy and stability of active pharmaceutical ingredients. Its synthesis typically involves the borylation of halogenated aromatic precursors under mild conditions, a process that improves yield and selectivity. The tert-butylcarbamate (Boc) protecting group present in the molecule ensures stability during synthetic transformations, allowing selective deprotection in later steps.

One of the primary applications of this substance lies in its use as a building block for kinase inhibitors, targeting various cancers and inflammatory diseases. Its boronic ester moiety facilitates Suzuki-Miyaura cross-coupling reactions, which are pivotal for constructing biaryl and heteroaryl compounds. These structural motifs are prevalent in molecules that modulate biological pathways linked to disease progression.

Furthermore, the compound plays a critical role in medicinal chemistry programs focused on optimizing lead candidates. Researchers exploit its reactivity to generate libraries of derivatives that are subsequently screened for pharmacological activity. This approach accelerates the identification of potent inhibitors with improved pharmacokinetics and reduced off-target effects.

The continued exploration of boronic acid esters, including this compound, underscores the importance of developing robust synthetic routes and expanding the chemical space available for drug discovery.

References

2018. Encorafenib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0134