Communications- Preparation and Storage of Diphenylborinic Acid and Its Anhydride.

Chremos, G; Weidmann, H; Zimmerman, Howard K.

doi:10.1021/jo01064a641

Cited by 32 publications

(13 citation statements)

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“…These compounds, which all contain a B-N bond, were obtained via the reaction of diphenylborinic acid with the corresponding α-amino acid (Fig. 2) rather than via the previously reported methods (Chremos et al, 1961;Flückiger et al, 1984;Farfán et al, 1993;Trujillo et al, 1998). The compounds (3a-j) were assayed using several different apoptotic indicator models, such as the inhibitory effect on cell growth measured by the MTT [3-(4,5-dimethylthiazo-2-yl)-2,5-diphenyl-tetrazolium bromide] assay, phosphatidylserine membrane externalization measured by Annexin V, and DNA distribution (sub-G 0 /G 1 peak) measured by PI staining, the last two using flow cytometry.…”

Section: Introductionmentioning

confidence: 99%

In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells

Velasco

Trujillo‐Ferrara²,

Castillo³

et al. 2007

Life Sciences

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Section: Introductionmentioning

confidence: 99%

In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells

Velasco

Trujillo‐Ferrara²,

Castillo³

et al. 2007

Life Sciences

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“…Solvents were used without further purification. The phenylborinic acid (Ph 2 BOH) was prepared in situ as previously reported in the literature . Melting points were determinate on an Electrothermal Mel‐Temp apparatus and are uncorrected.…”

Section: Methodsmentioning

confidence: 99%

Fluorescent boron Schiff bases dyes for staining silk fibroin: Green synthesis, structural characterization, DFT, and photophysical properties

Molina‐Paredes

Jiménez-Pérez

Lara‐Cerón

et al. 2018

Applied Organom Chemis

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Five novel organoboron complexes were synthesized in just 15 min via microware irradiation, by one pot multicomponent reactions between diverse aryl aldehydes with benzoylhydrazide, or 4-nitrobenzoylhidrazine and diphenyl boronic acid, in a 1:1:1 ratio in benzene. The products were characterized by 1 H, 13 C, 11 B NMR, UV, IR, spectroscopy and high-resolution mass spectrometry (HRMS). The molecular structure was also determined by singlecrystal X-ray diffraction for two complexes, which showed the tetra-coordination of the boron atoms giving rise to distorted tetrahedral molecular geometry with a strong intermolecular C-H···π interactions. In spite of the low quantum yields exhibited by the series in solution, some complexes stained uniformly the silk fibroins emitting enough fluorescence to allow its characterization by confocal microscopy. Boron as chelate center of the five complexes resulted not to be toxic for B16F10 cells, these compounds are appropriate for their used in medical applications.

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“…Compounds I and 2 wcrc prcparetl by reacting thc appropriate aminoalcohol with an equimolar quantity ofdiphcnylborinic acid (obtained by acid hydrolysis of (2-aminoethanolnto)cliphenylboron) in ethanol/diethyl ether (6). A small amount of thc molecular complex 3 was isolated from thc reaction mixture during thc preparation of 2 as colorless crystals suitable for X-ray analysis.…”

Section: Methodsmentioning

confidence: 99%

“…Colorless crystals of 1 and 2 were obtained by rccsystallization from ethanol. Monoclinic, (1 = 9.6717 (13), b = 9.5867 (6). c = 14.452(2) A. P = 99.500 (7) tomcter.…”

Section: Methodsmentioning

confidence: 99%

Structural studies of organoboron compounds. XV. Crystal and molecular structures of (3-aminopropanolato)diphenylboron, (2-N,N-dimethylaminoethanolato)diphenylboron, and (2-N,N-dimethylaminoethanolato)diphenylboron – diphenylborinic acid (1:1)

Rettig¹,

Trotter²

1983

Can. J. Chem.

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Crystals of (3-aminopropanolato)diphenylboron are monoclinic, a = 9.6717(13). b = 9.8867(6), c = 14.452(2) Å, β = 99.500(7)°, Z = 4, space group P21/n: those of (2-N,N-dimethylaminoethanolato)diphenylboron are monoclinic, a = 7.0721(4), b = 16.8829(4), c = 12.0975(8) Å, β = 97.875(3)°, Z = 4, space group Cc; and those of (2-N,N-dimethylaminoethanolato)diphenylboron – diphenylborinic acid (1:1) are monoclinic. a = 11.3231(10). b = 19.3190(12). c = 12.2451(11) Å, β = 109.321(4)°, Z = 4, space group P21/n. All three structures were solved by direct methods and were refined by full-matrix least-squares procedures to final R values of 0.038. 0.031, and 0.040 for 1522, 1649, and 2420 reflections with I ≥ 3σ(I) respectively. Each structure contains a tetrahedrally coordinated boron atom. The libration-corrected B—O, B—N, and mean B—C distances are: 1.481(2), 1.643(3), and 1.623(3) Å for (3-aminopropanolato)diphenylboron; 1.476(2), 1.691 (2), and 1.625(7) Å for (2-N,N-dimethylaminoethanolato)diphenylboron. The Ph2BOH molecule contains a trigonal-planar boron atom with B—O = 1.354(3) Å and mean B—C = 1.572(3) Å.

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Communications- Preparation and Storage of Diphenylborinic Acid and Its Anhydride.

Cited by 32 publications

References 0 publications

In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells

In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells

Fluorescent boron Schiff bases dyes for staining silk fibroin: Green synthesis, structural characterization, DFT, and photophysical properties

Structural studies of organoboron compounds. XV. Crystal and molecular structures of (3-aminopropanolato)diphenylboron, (2-N,N-dimethylaminoethanolato)diphenylboron, and (2-N,N-dimethylaminoethanolato)diphenylboron – diphenylborinic acid (1:1)

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