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
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) |
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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