156742-45-9

Basic information

• Product Name: Boronic acid, [2-[[(9-anthracenylmethyl)methylamino]methyl]phenyl]-
• CAS NO: 156742-45-9
• Molecular Formula: C23H22BNO2
• Molecular Weight: 355.244
• Mol File: 156742-45-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Boronic acid, [2-[[(9-anthracenylmethyl)methylamino]methyl]phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, [2-[[(9-anthracenylmethyl)methylamino]methyl]phenyl]-(156742-45-9)
• EPA Substance Registry System: Boronic acid, [2-[[(9-anthracenylmethyl)methylamino]methyl]phenyl]-(156742-45-9)

Safety Data

• Hazardous Substances Data: 156742-45-9(Hazardous Substances Data)

Upstream product

• 73356-19-1 9-[(methylamino)methyl]anthracene 
• 7481-16-5 2,4,6-Tris[o-(bromomethyl)phenyl]boroxine 
• 91983-14-1 2-bromomethylphenylboronic acid 
• 156742-47-1 2,4,6-tris-(2-bromomethyl-phenyl)-cyclotriboroxane 
• 73356-20-4 N-(9-anthrylmethylidene)methylamine 
• 642-31-9 9-anthracene aldehyde 
• 174900-86-8 propane-1,3-diyl(o-(bromomethyl)phenyl)boronate 

Downstream Products

• 1160173-64-7 C₁₄H₉CH₂N(CH₃)CH₂C₆H₄B(OCH₃)2 

Relevant articles and documents

Anion recognition by anthracene appendedortho-aminomethylphenylboronic acid: a new PET-based sensing mechanism

Interactions of anthracene appendedortho-aminomethylphenylboronic acid1with 20 organic and inorganic anions have been studied by fluorescence,1H and11B NMR titrations in DMSO. Carboxylate, phosphate and sulphate anions form hydrogen bonded complexes with the B(OH)2group producing a strong turn-off fluorescence response attributed to the enhanced photoinduced electron transfer (PET) resulting from the removal of the intramolecular hydrogen bond between boronic acid and the amino groups of1. The preferable hydrogen bonding interaction of1with a dihydrogen phosphate anion, which typically coordinates directly to the B(iii) atom, is confirmed by DFT structural optimization. The logarithms of the binding constants for the majority of anions correlate linearly with the pKaof their conjugate acids, but sulfate and hydrogen oxalate show strong positive deviations. Anomalously strong binding of hydrogen oxalate is attributed to the formation of the covalent cyclic ester. In the series of monoanions of dicarboxylic acids HOOC-R-COO?, the monoanion of malonic acid induces a strong opposite turn-on effect, demonstrating the ability of1to act as a ditopic receptor through the simultaneous binding of basic and acid groups of the guest to the boronic acid and amino groups of the receptor, respectively. The results of this study demonstrate the possibility of successful manipulation of the efficiency of PET produced by the anthracene attached aminomethyl group by the guest hydrogen bonding in addition to well-known protonation and metal coordination effects.

Novel saccharide-photoinduced electron transfer sensors based on the interaction of boronic acid and amine

Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid-base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid-base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron-nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.