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HomeProduct name listTri-tert-butylphosphine tetrafluoroborate

Tri-tert-butylphosphine tetrafluoroborate

Synonym(s):[(t-Bu)3PH]BF4;TTBP · HBF4

  • CAS NO.:131274-22-1
  • Empirical Formula: C12H28P.BF4
  • Molecular Weight: 290.13
  • MDL number: MFCD04039975
  • EINECS: 672-603-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-07-26 16:31:05
Tri-tert-butylphosphine tetrafluoroborate Structural

What is Tri-tert-butylphosphine tetrafluoroborate?

Chemical properties

white to light yellow crystal powde

The Uses of Tri-tert-butylphosphine tetrafluoroborate

suzuki reaction
Hindered Phosphine salt employed with a Pd(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Also used in Heck coupling of non-activated vinyl tosylates with electron deficient olefins.
Ligand used in the Pd-catalyzed enantioselective α?arylation of N-boc-pyrrolidine.

The Uses of Tri-tert-butylphosphine tetrafluoroborate

Tri-tert-butylphosphonium Tetrafluoroborate is used in the synthesis of substituted biaryl compounds via palladium catalyzed tandem Heck-direct arylation and tandem- sequential Heck-direct arylation-hydrogenation. Also used in the synthesis of a novel organic dye with fluorenone as conjugation bridge which is used in dye sensitized solar cells.

What are the applications of Application

Tri-tert-butylphosphonium tetrafluoroborate is a ligand used in the palladium-catalyzed enantioselective alfa-arylation of N-boc-pyrrolidine. It is also used with a palladium(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Further, it is used in the Heck coupling of vinyl tosylates with olefins.

Preparation

Addition of HBF4 to a solution of tri-tert-butylphosphine in methylene chloride. Separation of the organic layer and removal of the solvent gives analytically pure Tri-tert-butylphosphine tetrafluoroborate.

storage

Tri-tert-butylphosphine tetrafluoroborate is indefinitely stable as a solid and in solution and requires no special handling. This compound is considered non-hazardous. Protection from oxygen is required in the presence of the base, as the highly air-sensitive tri-tert-butylphosphine will be formed.

Properties of Tri-tert-butylphosphine tetrafluoroborate

Melting point: 261 °C(lit.)
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
solubility  Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
form  Crystals and Chunks
color  White
Water Solubility  Soluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water.
Sensitive  Hygroscopic
BRN  8813613
InChI InChI=1S/C12H28P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h13H,1-9H3;/q2*-1
CAS DataBase Reference 131274-22-1(CAS DataBase Reference)

Safety information for Tri-tert-butylphosphine tetrafluoroborate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Tri-tert-butylphosphine tetrafluoroborate

InChIKey YSTLBJVHZMEEAC-UHFFFAOYSA-N
SMILES [P-](C(C)(C)C)(C(C)(C)C)C(C)(C)C.[B-](F)(F)(F)F

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