857197-21-8

Basic information

• Product Name: 2,4,6-tris(4-formylphenyl)boroxin
• Synonyms: 2,4,6-tris(4-formylphenyl)boroxin
• CAS NO: 857197-21-8
• Molecular Weight: 395.779
• Mol File: 857197-21-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2,4,6-tris(4-formylphenyl)boroxin(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-tris(4-formylphenyl)boroxin(857197-21-8)
• EPA Substance Registry System: 2,4,6-tris(4-formylphenyl)boroxin(857197-21-8)

Safety Data

• Hazardous Substances Data: 857197-21-8(Hazardous Substances Data)

Upstream product

• 87199-17-5 4-formylphenylboronic acid, 

Downstream Products

• 1225073-73-3 4-(naphthalen-2-ylmethyl)benzaldehyde 
• 66-98-8 4,4'-diformylbiphenyl 

Relevant articles and documents

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which Suzuki–Miyaura cross couplings gave access to silicon rhodamines in poor to moderate yields, we wanted to improve these first valuable experimental results. Results: The preparation of the xanthene triflate was enhanced and several boron sources were screened to find the optimal coupling partner. After optimization of the palladium catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction. Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines functionalized with free acid moieties are directly accessible in contrast to previously described methods.

Mild and ligand-free Pd(II)-catalyzed conjugate additions to hindered γ-substituted cyclohexenones

Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered γ-substituted cyclohexenones. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.