N-(diphenylmethylene)-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-((triisopropylsilyl)ethynyl)naphthalen-2-amine
[CAS# 2816821-08-4]

Identification

• Classification: Organic raw materials >> Organosilicon compound
• Name: N-(diphenylmethylene)-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-((triisopropylsilyl)ethynyl)naphthalen-2-amine
• Synonyms: N-[6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-[2-tri(propan-2-yl)silylethynyl]naphthalen-2-yl]-1,1-diphenylmethanimine
• Molecular Formula: C₄₀H₄₇BFNO₂Si
• Molecular Weight: 631.70
• CAS Registry Number: 2816821-08-4
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC3=C2C(=C(C=C3)F)C#C[Si](C(C)C)(C(C)C)C(C)C)N=C(C4=CC=CC=C4)C5=CC=CC=C5

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338-P302+P352

Discovory and Applicatios

N-(diphenylmethylene)-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-((triisopropylsilyl)ethynyl)naphthalen-2-amine is a synthetically engineered polycyclic aromatic compound incorporating several important functional groups often utilized in the field of advanced materials chemistry and complex organic synthesis. The structure is based on a naphthalene scaffold, heavily substituted to serve as a multifunctional building block or intermediate in the development of organic semiconductors, cross-coupling partners, or advanced photonic materials.

The core naphthalene unit provides a rigid, planar, and π-conjugated framework that supports extended electronic delocalization. This characteristic makes substituted naphthalenes useful in the design of organic electronics, where their planar structure facilitates π-stacking interactions and efficient charge transport. The substitution pattern of this molecule significantly enhances its synthetic utility and electronic tunability.

At the 2-position of the naphthalene ring, there is an amine group that has been derivatized as an imine through condensation with diphenylmethanone, yielding a diphenylmethylene-protected amine. This form of protection stabilizes the amine during reactions and allows selective transformations without exposing the lone pair to unwanted reactivity. The diphenylmethylene group also contributes to the molecule's steric bulk and lipophilicity, which can influence solubility and reaction conditions.

The 4-position of the naphthalene ring is substituted with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane moiety, one of the most common boron-containing protecting groups in modern synthetic chemistry. This boronic ester enables Suzuki-Miyaura cross-coupling reactions, one of the most powerful carbon–carbon bond-forming methods used in the construction of biaryl compounds, heterocycles, and conjugated polymers. The dioxaborolane ring offers excellent air and moisture stability, while still being reactive under palladium catalysis with organohalides or triflates. The presence of this boronic ester significantly broadens the molecule's synthetic versatility.

At the 5-position, the molecule contains a triisopropylsilyl (TIPS)-protected ethynyl group. Alkynes protected with TIPS are stable under various reaction conditions and can be selectively deprotected under fluoride ion treatment. The alkyne moiety introduces further potential for coupling reactions (e.g., Sonogashira, click chemistry) and also extends the conjugation of the molecule. The use of bulky TIPS groups also helps to modulate solubility and prevent undesired polymerization or aggregation.

A fluorine atom is installed at the 6-position of the naphthalene ring, contributing electronic effects via inductive and resonance pathways. Fluorine substituents are often employed to modulate the electronic properties of aromatic compounds, tuning their reactivity, acidity, and interactions with biological or electronic targets. In photonic applications, fluorination can affect emission wavelengths and quantum yields.

Together, the presence of the diphenylmethylene-protected amine, the dioxaborolane boronic ester, the TIPS-protected alkyne, and the electron-withdrawing fluorine group creates a molecule of high synthetic utility. It can serve as a key intermediate in multistep syntheses leading to polyfunctional aromatics, functionalized π-systems, or molecules used in optoelectronic applications such as OLEDs, OFETs, or photovoltaic materials.

This compound is likely to have been designed for use in a modular synthetic strategy, where the boronic ester and ethynyl substituent act as orthogonal coupling handles for the stepwise construction of increasingly complex aromatic architectures. Its overall design reflects modern approaches in organic synthesis emphasizing stability, modularity, and multifunctionality.