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Merck
CN

358835

Diphenylborinic anhydride

95%

Synonym(s):

Oxybis(diphenylborane), Tetraphenyldiboroxane

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About This Item

Linear Formula:
(C6H5)2BOB(C6H5)2
CAS Number:
4426-21-5
Molecular Weight:
346.04
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
57649443
MDL number:
MFCD00042663
Beilstein/REAXYS Number:
2950331

Key Documents

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Product Name

Diphenylborinic anhydride, 95%

InChI

1S/C24H20B2O/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)27-26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

SMILES string

O(B(c1ccccc1)c2ccccc2)B(c3ccccc3)c4ccccc4

InChI key

SNQFEECGHGUHBK-UHFFFAOYSA-N

assay

95%

form

solid

mp

135-140 °C (lit.)

fluorescence

λex 366 nm; λem 475 nm (after derivatization)

storage temp.

2-8°C

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Application

Diphenylborinic anhydride (DPBA) may be used for the separation and determination of α-amino acids by boroxazolidone formation. DPBA, an analogue of the vascular gap junction channel blocker, 2-aminoethoxydiphenyl borate (2-APB), may be use in gap junctions channel studies.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBP4888V
1451802V
1451802
1341330
16201TC

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C J Strang et al.
Analytical biochemistry, 178(2), 276-286 (1989-05-01)
Reaction of an alpha-amino acid (alpha-AA) with 1,1-diphenylborinic acid (DPBA) leads to the formation of a kinetically stable adduct at pH 2-5 in which both the alpha-amino and the alpha-carboxyl groups are bound to boron forming a cyclic mixed anhydride
Ke-Tao Ma et al.
American journal of physiology. Heart and circulatory physiology, 300(1), H335-H346 (2010-11-03)
2-Aminoethoxydiphenyl borate (2-APB) analogs are potentially better vascular gap junction blockers than others widely used, but they remain to be characterized. Using whole cell and intracellular recording techniques, we studied the actions of 2-APB and its potent analog diphenylborinic anhydride
Yan Yang et al.
Biological & pharmaceutical bulletin, 34(9), 1390-1397 (2011-09-02)
2-Aminoethoxydiphenyl borate (2-APB) has recently been demonstrated to inhibit gap junction (GJ) channels, whereas the underlying mechanisms are still unknown. Using mouse TM₄ Sertoli cell which expresses connexin43 (Cx43), we explored the effects of 2-APB and its analogues on dye-coupling

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