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358835

Sigma-Aldrich

Diphenylborinic anhydride

95%

Synonym(s):
Oxybis(diphenylborane), Tetraphenyldiboroxane
Linear Formula:
(C6H5)2BOB(C6H5)2
CAS Number:
Molecular Weight:
346.04
Beilstein:
2950331
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

95%

mp

135-140 °C (lit.)

fluorescence

λex 366 nm; λem 475 nm (after derivatization)

storage temp.

2-8°C

SMILES string

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

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

InChI key

SNQFEECGHGUHBK-UHFFFAOYSA-N

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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.

Packaging

1 g in glass bottle
250 mg in glass bottle

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

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
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
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

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