Tri-tert-butylphosphine tetrafluoroborate

Base Information

• Chemical Name: Tri-tert-butylphosphine tetrafluoroborate
• CAS No.: 131274-22-1
• Molecular Formula: C12H28P^.BF4
• Molecular Weight: 290.133
• Hs Code.: 29319090
• European Community (EC) Number: 672-603-2
• DSSTox Substance ID: DTXSID80370410
• Mol file: 131274-22-1.mol

Synonyms:tritert-butylphosphanium,tetrafluoroborate;Tri-tert-butylphosphonium Tetrafluoroborate;

Chemical Property of Tri-tert-butylphosphine tetrafluoroborate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 261 °C(lit.)
• PSA: 13.59000
• LogP: 5.89610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 290.1957807
• Heavy Atom Count: 18
• Complexity: 147

Purity/Quality:

98% ^*data from raw suppliers

Tri-tert-butylphosphonium Tetrafluoroborate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
• Uses: suzuki reactionHindered 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. 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.

Technology Process of Tri-tert-butylphosphine tetrafluoroborate

There total 5 articles about Tri-tert-butylphosphine tetrafluoroborate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

tri-tert-butyl phosphine (13716-12-6) → tri tert-butylphosphoniumtetrafluoroborate (131274-22-1)

Guidance literature:

With tetrafluoroboric acid; In dichloromethane; water; toluene; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.dyepig.2011.03.022

Reference yield: 90.0%

tris(tert-butyl)phosphane-borane(1:1) → tri tert-butylphosphoniumtetrafluoroborate (131274-22-1)

Guidance literature:

With tetrafluoroboric acid diethyl ether; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2017998

Reference yield: 87.0%

sodium tetrafluoroborate (13755-29-8) + tri-tert-butyl phosphine (13716-12-6) → tri tert-butylphosphoniumtetrafluoroborate (131274-22-1)

Guidance literature:

tri-tert-butyl phosphine; With hydrogenchloride; In water; at 20 ℃; for 1h;

sodium tetrafluoroborate; In water; for 1h; Reagent/catalyst;

upstream raw materials:

tri-tert-butyl phosphine

tert-butylmagnesium chloride

acetonitrile

sodium tetrafluoroborate

Downstream raw materials:

(2E)-3-(2-Phenyl-5-pyrimidinyl)-2-propenoic Acid Methyl Ester

(2E)-3-[4-(2-Pyrimidinyl)phenyl]-2-butenoic Acid Ethyl Ester

bis(tri-t-butylphosphine)palladium⁽⁰⁾

tert-butyl 2-(benzamido)-4-(4-nitrophenoxy)benzoate

Refernces

• 1、 Habraken, Evi R. M.,van Leest, Nicolaas P.,Hooijschuur, Pim,de Bruin, Bas,Ehlers, Andreas W.,Lutz, Martin,Slootweg, J. Chris. "Aryldiazonium Salts as Nitrogen-Based Lewis Acids: Facile Synthesis of Tuneable Azophosphonium Salts". . p. 11929 - 11933. Retrieved 2018.
• 2、 Dinalp, Haluk,Akar, Zuhal,Zafer, Ceylan,Li, Sddk. "Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes". experimental part. p. 182 - 191. Retrieved 2012/01/13.