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Key Documents

T25402

Sigma-Aldrich

Sodium tetraphenylborate

ACS reagent, ≥99.5%

Synonym(s):

Tetraphenylboron sodium

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About This Item

Linear Formula:
(C6H5)4BNa
CAS Number:
Molecular Weight:
342.22
Beilstein:
3599783
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

grade

ACS reagent

Quality Level

Assay

≥99.5%

form

powder, crystals or granules

reaction suitability

reagent type: catalyst
core: boron

clarity of soln

passes test

loss

≤0.5% loss on drying

pH

8 (20 °C, 50 g/L)

SMILES string

[Na+].c1ccc(cc1)[B-](c2ccccc2)(c3ccccc3)c4ccccc4

InChI

1S/C24H20B.Na/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;/q-1;+1

InChI key

HFSRCEJMTLMDLI-UHFFFAOYSA-N

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General description

NaBPh4 acts as a convenient source of phenyl groups in the catalytic process, enabling the synthesis of phenylated products.

Application

Generates stable, crystalline N-acylammonium salts by ion exchange. Couples with vinyl and aryl triflates to form arylalkenes and biaryls.
Sodium tetraphenylborate can form hydrophobic salts with amines, ammonium ions, and large alkali metal ions such as cesium or rubidium ions. Hence it is commonly used in gravimetric analysis as a precipitating agent.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Rhodium-catalyzed phenylation of N-arylsulfonyl aldimines with sodium tetraphenylborate or trimethyl (phenyl) stannane
Ueda M and Miyaura N
Journal of Organometallic Chemistry, 595(1), 31-35 (2000)
Tetrahedron Letters, 33, 4815-4815 (1992)
Recovery of ammonium and cesium ions from aqueous waste streams by sodium tetraphenylborate.
Ponder SM & Mallouk TE.
Industrial & Engineering Chemistry Research, 38(10), 4007-4010 (1999)
The Journal of Organic Chemistry, 57, 5136-5136 (1992)
D C Kapsimali et al.
Talanta, 80(3), 1311-1317 (2009-12-17)
Two different derivatizing reagents were tested for the development of a fast and sensitive method for the determination of selenites (Se(IV)) in human urine. The reagents were sodium tetraethylborate (NaBEt(4)) and tetraphenylborate (NaBPh(4)), respectively, and the procedure is based on

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