223440-94-6

Basic information

• Product Name: 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN
• Synonyms: TRIS(3,4,5-TRIFLUOROPHENYL)CYCLOBOROXANE;2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN;3,4,5-TRIFLUOROPHENYLBORONIC ANHYDRIDE;3,4,5-Trifluorophenylboronic Anhydride Tris(3,4,5-trifluorophenyl)cycloboroxane;2,4,6-Tris(3,4,5-trifluorophenyl)-1,3,5,2,4,6-trioxatriborinane
• CAS NO: 223440-94-6
• Molecular Formula: C₁₈H₆B₃F₉O₃
• Molecular Weight: 473.66
• Product Categories: B (Classes of Boron Compounds);Boronic Acids
• Mol File: 223440-94-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 375.9°C at 760 mmHg
• Flash Point: 181.1°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.63E-05mmHg at 25°C
• Refractive Index: 1.486
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN(223440-94-6)
• EPA Substance Registry System: 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN(223440-94-6)

Safety Data

• Hazardous Substances Data: 223440-94-6(Hazardous Substances Data)

Usage

General Description

2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN is a chemical compound with the molecular formula C18H6BF9O3. It is a boron-based compound that contains three triarylboroxine groups. 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN is commonly used in organic synthesis and materials science. It has a variety of applications, including as a precursor for the preparation of boron-containing polymers and as a building block for the synthesis of various organic molecules. 2,4,6-TRIS(3,4,5-TRIFLUOROPHENYL)BOROXIN has gained attention for its unique properties and potential applications in various fields of research and industry.

InChI:InChI=1/C18H6B3F9O3/c22-10-1-7(2-11(23)16(10)28)19-31-20(8-3-12(24)17(29)13(25)4-8)33-21(32-19)9-5-14(26)18(30)15(27)6-9/h1-6H

Upstream product

• 143418-49-9 3,4,5-trifluorophenylboronic acid 
• 103-82-2 phenylacetic acid 

Downstream Products

• 143418-49-9 3,4,5-trifluorophenylboronic acid 
• 1229514-49-1 (3,4,5-trifluorophenyl)benzylsulfide 
• 1229514-61-7 bis(3,4,5-trifluorophenyl)sulfide 
• 1229514-37-7 (3,4,5-trifluorophenyl)-2,3-dichlorophenylsulfide 
• 1229514-20-8 (3,4,5-trifluorophenyl)-4-chlorophenylsulfide 
• 1229514-46-8 (3,4,5-trifluorophenylthio)-3-propanoic acid 
• 1229514-26-4 (3,4,5-trifluorophenyl)-4-nitrophenylsulfide 
• 1229514-14-0 (3,4,5-trifluorophenyl)-4-tolylsulfide 
• 1229514-17-3 (3,4,5-trifluorophenyl)-4-bromophenylsulfide 
• 1229514-40-2 (3,4,5-trifluorophenyl)-4-hydroxyphenylsulfide 
• 1229514-23-1 (3,4,5-trifluorophenyl)-4-fluorophenylsulfide 
• 1229514-31-1 (3,4,5-trifluorophenyl)-2,4-dimethylphenylsulfide 
• 1229514-43-5 (3,4,5-trifluorophenyl)-2-aminophenylsulfide 
• 1229514-34-4 (3,4,5-trifluorophenyl)-4-isopropylphenylsulfide 

Relevant articles and documents

Mechanistic insights into boron-catalysed direct amidation reactions

The generally accepted monoacyloxyboron mechanism of boron-catalysed direct amidation is brought into question in this study, and new alternatives are proposed. We have carried out a detailed investigation of boron-catalysed amidation reactions, through study of the interaction between amines/carboxylic acids and borinic acids, boronic acids and boric acid, and have isolated and characterised by NMR/X-ray crystallography many of the likely intermediates present in catalytic amidation reactions. Rapid reaction between amines and boron compounds was observed in all cases, and it is proposed that such boron-nitrogen interactions are highly likely to take place in catalytic amidation reactions. These studies also clearly show that borinic acids are not competent catalysts for amidation, as they either form unreactive amino-carboxylate complexes, or undergo protodeboronation to give boronic acids. It therefore seems that at least three free coordination sites on the boron atom are necessary for amidation catalysis to occur. However, these observations are not consistent with the currently accepted 'mechanism' for boron-mediated amidation reactions involving nucleophilic attack of an amine onto a monomeric acyloxyboron intermediate, and as a result of our observations and theoretical modelling, alternative proposed mechanisms are presented for boron-mediated amidation reactions. These are likely to proceed via the formation of a dimeric B-X-B motif (X = O, NR), which is uniquely able to provide activation of the carboxylic acid, whilst orchestrating the delivery of the amine nucleophile to the carbonyl group. Quantum mechanical calculations of catalytic cycles at the B3LYP+D3/Def2-TZVPP level (solvent = CH2Cl2) support the proposal of several closely related potential pathways for amidation, all of which are likely to be lower in energy than the currently accepted mechanism.