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A10909 Sodium tetraphenylborate, 99%

CAS Number
143-66-8
Synonyms
Tetraphenylboron sodium

Sodium tetraphenylborate, 99%

MDL
MFCD00011494
EINECS
205-605-5

Chemical Properties

Formula
C24H20BNa
Formula Weight
342.23
Melting point
>300°
Storage & Sensitivity
Light Sensitive. Ambient temperatures.
Solubility
Soluble in water and ethanol.

Applications

Sodium tetraphenylborate is used as a precipitating reagent for potassium and as a protecting agent to protect amino acids. It is used in the preparation of N-acylammonium salts. It finds application as a phenyl donor in palladium-catalyzed cross-coupling reactions to prepare arylalkenes and biaryl compounds. It is used in inorganic and organometallic chemistry due to its solubility in nonpolar solvents. Furthermore, it is involved in the isolation of complexes having dinitrogen ligands.

Notes

Light sensitive. Incompatible with strong acids and strong oxidizing agents.

Literature References

Reagent for potassium by precipitation: Anal. Chem., 29, 1044 (1957).

Has been used to protect amino acids by formation of a diphenylborinate chelate, stable to AcOH or TFA, but cleaved by base: Tetrahedron, 39, 2995 (1983); Liebigs Ann. Chem., 127 (1989):

The cross coupling of tetraphenylborates or aryl boronic acids with aryl halides is catalyzed by Pd(OAc)2 in aqueous solutions: Dokl. Chem. (Engl. Transl.), 315, 354 (1990); see also: Gazz. Chem. Ital., 120, 779 (1990). Cross couples with vinyl and aryl triflates under Pd catalysis: Tetrahedron Lett., 35, 4835 (1992); 33, 4815 (1992). Similarly, allyl acetates are phenylated: Tetrahedron Lett., 31, 7453 (1990).

Howa, J. D.; Lott, M. J.; Ehleringer, J. R. Isolation and stable nitrogen isotope analysis of ammonium ions in ammonium nitrate prills using sodium tetraphenylborate. Rapid Commun. Mass Spectrom. 2014, 28 (13), 1530-1534.

Boruń, A.; Trzcińska, I.; Bald, A. Conductometric Studies of Sodium Iodide, Sodium Tetraphenylborate, Tetrabutylammonium Iodide, and Sodium Tetrafluoroborate in 1-Propanol at Temperatures from (283.15 to 318.15) K. Int. J. Electrochem. Sci. 2014, 9, 7805-7818.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,8690
Beilstein
3599783
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
ED3362500

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