2001005-77-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a key intermediate in the synthesis of various pharmaceuticals for its high reactivity and ability to participate in challenging cross-coupling reactions.
Used in Agrochemical Development:
In the agrochemical industry, 2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is utilized as a building block for the creation of new agrochemicals, leveraging its reactivity in cross-coupling reactions to form complex molecules with potential pesticidal properties.
Used in Organic Electronics:
2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is employed as a component in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, due to its compatibility with the synthesis of conductive and semiconductive polymers.
Used in Suzuki-Miyaura Coupling Reactions:
A prominent application of ITDF is in the Suzuki-Miyaura coupling reaction, a widely used method for the formation of carbon-carbon bonds. Its steric hindrance and reactivity make it particularly useful for facilitating cross-coupling reactions that are otherwise difficult to achieve with less reactive boronic esters.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 480424-94-0 N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide 

Relevant academic research and scientific papers

Synthesis, Crystal Structure, and DFT Study of a New Derivative of Pyrido[2,3-d]pyrimidine

Abstract: N-{4-[(6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy]phenyl}morpholine-4-carboxamide has been synthesized as a derivative of pyrido[2,3-d]pyrimidine that demonstrates antitumor, antibacterial, anti-inflammatory, and antimicrobial activities. Synthesis of the target compound based on 2-aminonicotinic acid as the starting material has included its esterification, bromination, cyclization, and substitution reactions. Structure of the product is confirmed by 1H and 13C NMR, FT-IR, and single-crystal X-ray diffraction (XRD). The optimized structure, electrostatic potential and frontier molecular orbitals (FMO) of the compound have been approached by DFT calculations. The compound demonstrates antiproliferative activity on A375 cells.

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Synthesis and stability study of isocyano aryl boronate esters and their synthetic applications

A facile synthesis of isocyano arylboronate esters is reported. Although tri-coordinate boron functional groups are commonly recognized as vulnerable to nucleophilic attack, the newly reported tri-coordinate isocyano arylboronate esters were found to be stable, albeit owing to the presence of an isocyano group. Theoretical calculations, using the DFT/B3LYP/6-31G(d,p) method, revealed that the electron delocalization between the aryl group and the boron atom might contribute to this stability. UV-vis spectroscopic investigations on 2-(4-isocyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2a) were in agreement with the theoretical studies, showing a red-shifted absorption compared with that of phenylisonitrile. The reported strategy allows boronate ester substrates to survive throughout two-step operations. Two of the compounds synthesized were successfully exploited in Ugi and Passerini multicomponent reactions to afford corresponding products. In addition, two boron-containing tetrazoles were also prepared under environmentally benign conditions. These results demonstrated that functionalized isocyanides are stable and can be used as strategically as synthetic building blocks.