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Tri-tert-butylphosphine tetrafluoroborate

Tri-tert-butylphosphine tetrafluoroborate

CAS: 131274-22-1

Molecular Formula: C12H28P.BF4

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Tri-tert-butylphosphine tetrafluoroborate - Names and Identifiers

Name Tri-tert-butylphosphine tetrafluoroborate
Synonyms Tri-tert-butylphosphoniuM tetr
Tri-t-butylphosphoniumtetrafluoroborate
Tri-tert-butylphosphine tetrafluoborate
Tri-T-Butylphosphonium Tetrafluoroborate
Tri-tert-butylphosphine tetrafluoroborate
Tri-Tert-Butylphosphonium Tetrafluoroborate
Tri-(T-Butyl)Phosphonium Hydrogen Hbf4 Salt
tri-tert-butylphosphine fluoroboric acid adduct
fluoroboric acid tri-tert-butylphosphine adduct
Tri-Tert-Butylphosphine Tetrafluoroboric Acid Adduct
CAS 131274-22-1
EINECS 672-603-2
InChI InChI=1/C12H27P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h1-9H3;/q;-1/p+1
InChIKey YSTLBJVHZMEEAC-UHFFFAOYSA-N

Tri-tert-butylphosphine tetrafluoroborate - Physico-chemical Properties

Molecular FormulaC12H28P.BF4
Molar Mass290.13
Melting Point261°C(lit.)
Water SolubilitySoluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water.
Solubility Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
AppearanceBright yellow crystal
ColorWhite
BRN8813613
Storage Conditionunder inert gas (nitrogen or Argon) at 2-8°C
SensitiveHygroscopic
MDLMFCD07189501
Physical and Chemical PropertiesSensitivity: hydrogen
WGK Germany:3

Tri-tert-butylphosphine tetrafluoroborate - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
Risk CodesR36/37/38 - Irritating to eyes, respiratory system and skin.
R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
Safety DescriptionS22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
UN IDsUN 1759 8/PG III
WGK Germany3
TSCANo
HS Code29319090
Hazard Class8
Packing GroupIII

Tri-tert-butylphosphine tetrafluoroborate - Reference Information

Open Data Unverified Data
Introduction Tritert-butylphosphine tetrafluoroborate, also known as tert-butylphosphine tetrafluoroborate, is an organic intermediate that can be obtained by the reaction of tert-butane chloride and phosphorus tribromide. It has been reported that it can be used to prepare α-aryl vinyl phosphonates, sensitizing materials and a sensitizing material.
application tri-tert-butylphosphine tetrafluoroborate is mainly used for highly active phosphine ligand catalysts. It is also used to n-boc the ligand of palladium-catalyzed enantioselective-arylation of pyrrolidine. It can also be used for the heck coupling reaction of unactivated vinyltoluenesulfonate with electron-deficient olefins.
Preparation Tritert-butylphosphine tetrafluoroborate can be obtained by the reaction of tert-butane chloride and phosphorus tribromide.
under the protection of nitrogen, 7.28g(1.05eq) of magnesium chips and 15.2g (1/8 of the total weight) of chloro-tert-butane THF solution (26.7g of chlorocyclohexane dissolved in 135mLTHF) are added into a 250mL four-mouth bottle, heated to 55~60 ℃, added 2 iodine to initiate successfully, and dropwise the remaining 105.5g (total 1.0eq) of chloro-tert-butane tetrahydrofuran solution while maintaining boiling reflux. after dropting, heat to reflux for 2h, cool to room temperature for later use, analyze and measure the concentration of 1.82±0.3mmol/g (about 154g). Under the protection of argon, 7.5g(0.182eq) and 70mLTHF of phosphorus tribromide are added into a 500mL four-mouth bottle, 988mg(0.0182eq) of cuprous iodide and 898mg(0.0364eq) of lithium bromide are added under room temperature stirring, 154g of format reagent is added at -15 ℃ at -10-5 ℃, stirred at low temperature for 2h, stirred at natural temperature for 4h, and monitored with GC to less than 1%, the main content is 80-85% and the impurity is 10-20%. After the reaction is finished, 50.6g(0.946eq) of 45.9% fluoroboric acid and 9.3g(0.092eq) of 15% ammonium chloride aqueous solution and 45g of water are added to another reaction bottle, the oil is layered, washed once with 50mL of water, the water layers are combined, and then extracted once with 50mL of dichloromethane. Merge the dichloromethane layer, add 20g of sodium sulfate to dry, then there is a small amount of water layer below, and add 20g of sodium sulfate to dry the liquid organic layer. Filtration, washing with 10mL of dichloromethane, concentration at 35-50 ℃ to obtain 24g of solid oil, adding 20mL of ethanol (1 volume) and heating to 78 ℃ for dissolution, adding 60mLMBTE (3 volume of ethanol) to cool down at 45 ℃ and crystallize at room temperature for 1h. After filtration, 6.7g of white solid was obtained by washing with 10mLMTBE. After drying, 7.5g of white solid was obtained with 55% yield and melting point> 260 ℃. The NMR spectrum was consistent with the literature.;
Last Update：2024-04-09 19:43:38
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Tri-tert-butylphosphine tetrafluoroborate
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