143-66-8
- Product Name：Borate(1-),tetraphenyl-, sodium (1:1)
- Molecular Formula：C24H20BNa
- Purity：99%
- Molecular Weight：
Product Details;
CasNo： 143-66-8
Molecular Formula： C24H20BNa
Appearance： white powder
143-66-8 Properties
- Molecular Formula:C24H20BNa
- Molecular Weight:342.224
- Appearance/Colour:white powder
- Melting Point:300 °C
- PSA：0.00000
- Density:1.15 g/cm3
- LogP:3.06400
143-66-8 Usage
Chemical Properties
white powder
Uses
Sodium Tetraphenylboroate is a salt that is commonly used in inorganic and organometallic chemistry as a precipitating agent. Sodium Tetraphenylboroate is also utilized for the preparation of N-acylam monium salts and in coordination chemistry due to their favourable solubility in nonpolar sovlents and their crystallinity.
Uses
Determination of potassium, ammonium, rubidium, and cesium.
Uses
As reagent for determination of potassium, ammonium, rubidium and cesium ions: Barnard, Buechl, Chemist-Analyst 48, 44, 49 (1959); Montequi, Serrano, An. R. Acad. Farm. 26, 107 (1960).
General Description
Sodium tetraphenylborate (Ph4BNa) undergoes rhodium-catalyzed addition reactions with N-phenylsulfonyl aldimines to afford R(Ph)CHNHSO2Ph.
Purification Methods
Dissolve the borate in dry MeOH and add dry Et2O. Collect the solid and dry it in a vacuum at 80o/2mm for 4hours. It can also be extracted (Soxhlet) using CHCl3, and it crystallises from CHCl3 as snow-white needles. It is freely soluble in H2O, Me2CO but insoluble in pet ether and Et2O. An aqueous solution has pH 5 and can be stored for days at 25 or lower, and for 5 days at 45o without deterioration. Its solubility in polar solvents increases with decrease in temperature [Wittig & Raff Justus Liebigs Ann Chem 573 204 1950]. The salt can also be recrystallised from acetone/hexane or CHCl3, or from Et2O/cyclohexane (3:2) by warming the solution to precipitate the compound. Dry it in a vacuum at 80o. It dissolves in Me2CO at 50-60o to give a clear solution. After standing at this temperature for 10minutes the mixture is filtered rapidly through a pre-heated Büchner funnel, cooled and the crystals are collected and dried in a vacuum desiccator at room temperature for 3days [Abraham et al. J Chem Soc, Faraday Trans 1 80 489 1984]. If the product gives a turbid aqueous solution, the turbidity can be removed by treating with freshly prepared alumina gel and filtering. [Beilstein 16 IV 1624.]
InChI: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
143-66-8 Relevant articles
Base-free palladium-catalyzed cross-coupling of arylsulfonium salts with sodium tetraarylborates
Osuka, Atsuhiro,Vasu, Dhananjayan,Yorimitsu, Hideki
, p. 3286 - 3291 (2020/10/20)
Palladium-catalyzed cross-coupling reactions of arylsulfonium salts with sodium tetraarylborates were found to proceed smoothly without recourse to an additional base, providing a new, reliable route to biaryls from organosulfur compounds.
Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes
Vasu, Dhananjayan,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 7162 - 7166 (2015/06/08)
Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.
Ligand-free, atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature
Zhou, Wen-Jun,Wang, Ke-Hu,Wang, Jin-Xian,Gao, Zhi-Rong
experimental part, p. 7633 - 7641 (2010/12/19)
The atom-efficient cross-coupling reaction of sodium tetraarylborates with aryl iodides and bromides was reported. The reaction can be performed directly using a catalytic system composed of palladium chloride, sodium carbonate and methanol (PdCl2/Na2CO3/MeOH) under heat-free conditions at room temperature in an open air conditions. The reactions carried out in an atom-efficient way as 4 equiv of aryl halides coupled effectively with 1 equiv of sodium tetraarylborates to furnish 4 equiv of the corresponding functionalized biaryls in good to excellent yields.
143-66-8 Process route
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- 13755-29-8
sodium tetrafluoroborate
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- 108-86-1,52753-63-6
bromobenzene
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- 143-66-8
sodium tetraphenyl borate
| Conditions | Yield |
|---|---|
|
With magnesium; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;
|
-
- 13755-29-8
sodium tetrafluoroborate
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- 100-58-3
phenylmagnesium bromide
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- 143-66-8
sodium tetraphenyl borate
| Conditions | Yield |
|---|---|
|
In diethyl ether; heating on water bath;
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|
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With sodium chloride; In diethyl ether; water; 2 h stirring, addn. of reaction mixture to a satd. aq. NaCl soln.; extrn. the aq. layer with ether two times, evapn. in vac.; recrystn. in ether at 0°C;
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|
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In diethyl ether; heating on water bath;
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|
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With NaCl; In diethyl ether; water; 2 h stirring, addn. of reaction mixture to a satd. aq. NaCl soln.; extrn. the aq. layer with ether two times, evapn. in vac.; recrystn. in ether at 0°C;
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143-66-8 Upstream products
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960-71-4
triphenylborane
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3244-41-5
potassium tetraphenylborate
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109-63-7
trifluoroborane diethyl ether
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100-58-3
phenylmagnesium bromide
143-66-8 Downstream products
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63689-31-6
3-cyclohexyl-2-oxa-3-aza-[4.4.4]propell-3-enium; tetraphenylborate(1-)
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16331-76-3
2-Brom-1,1-dimethyl-propoxy(3H6)dimethylsulfonium-tetraphenylborat
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50592-81-9
C24H20B(1-)*C9H15O4S(1+)
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