Reaction
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Tri-tert-butylphosphine tetrafluoroborate

Reaction
Product Name
Tri-tert-butylphosphine tetrafluoroborate
CAS No.
131274-22-1
Chemical Name
Tri-tert-butylphosphine tetrafluoroborate
Synonyms
TRI-TERT-BUTYLPHOSPHONIUM TETRAFLUOROBORATE;P(t-Bu)3HBF4;[(t-Bu)3PH]BF4;TRI-T-BUTYLPHOSPHONIUM TETRAFLUOROBORATE;TTBP HBF4;P(But)3.HBF4;Tri-tert-butylphos;Tri-tert-butylphosphoni;Tritert-butylphosphanium;Tri-tert-butylphosphonium
CBNumber
CB2385060
Molecular Formula
C12H28P.BF4
Formula Weight
290.13
MOL File
131274-22-1.mol
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Tri-tert-butylphosphine tetrafluoroborate Property

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
InChIKey
YSTLBJVHZMEEAC-UHFFFAOYSA-N
SMILES
[P-](C(C)(C)C)(C(C)(C)C)C(C)(C)C.[B-](F)(F)(F)F
CAS DataBase Reference
131274-22-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
22-24/25-36/37/39-26
RIDADR 
UN 1759 8/PG III
WGK Germany 
3
TSCA 
No
HazardClass 
8
PackingGroup 
III
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
578940
Product name
Tri-tert-butylphosphonium tetrafluoroborate
Purity
97%
Packaging
1g
Price
$104
Updated
2024/03/01
Sigma-Aldrich
Product number
578940
Product name
Tri-tert-butylphosphonium tetrafluoroborate
Purity
97%
Packaging
5g
Price
$221
Updated
2024/03/01
TCI Chemical
Product number
T2584
Product name
Tri-tert-butylphosphonium Tetrafluoroborate
Purity
>98.0%(T)
Packaging
1g
Price
$60
Updated
2024/03/01
TCI Chemical
Product number
T2584
Product name
Tri-tert-butylphosphonium Tetrafluoroborate
Purity
>98.0%(T)
Packaging
5g
Price
$177
Updated
2024/03/01
Alfa Aesar
Product number
L19752
Product name
Tri-tert-butylphosphonium tetrafluoroborate, 97%
Packaging
1g
Price
$97.65
Updated
2024/03/01
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Tri-tert-butylphosphine tetrafluoroborate Chemical Properties,Usage,Production

Reaction

  1. Air-stable, non-pyrophoric precursor of the Tri-t-butylphosphine ligand which is used in a variety of catalytic processes.
  2. Ligand for Suzuki cross-couplings.
  3. Ligand for Heck Reactions.
  4. Ligand for Stille Cross-couplings.
  5. Ligand for α-Arylation and vinylation of arylmandelic acid derivatives.
  6. Ligand for direct arylation of hetercycles
  7. Synthesis of benzocyclobutenes by C-H activation.
  8. Cross-coupling of Grignard reagents and aryl bromides.
  9. Palladium catalyzed annulation of haloanilines.
  10. Palladium-Catalyzed Acylation.
  11. Palladium Catalyzed Carbonylative Heck Reaction.
  12. Palladium-catalyzed aminosulfonylation.
  13. Palladium-catalyzed intramolecular C–O bond formation.
  14. Ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acid.



Chemical Properties

white to light yellow crystal powde

Uses

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.

Uses

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.

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.

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.

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.

Tri-tert-butylphosphine tetrafluoroborate Preparation Products And Raw materials

Raw materials

Preparation Products

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Tri-tert-butylphosphine tetrafluoroborate Suppliers

Acros Organics
Tel
--
Fax
--
Email
info@acros.com
Country
Belgium
ProdList
6772
Advantage
81
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View Lastest Price from Tri-tert-butylphosphine tetrafluoroborate manufacturers

XINXIANG RUNYU MATERIAL CO., LTD.
Product
Tri-tert-butylphosphine tetrafluoroborate 131274-22-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
0.99
Supply Ability
500kg
Release date
2021-11-30
Hebei Weibang Biotechnology Co., Ltd
Product
Tri-tert-butylphosphine tetrafluoroborate 131274-22-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 mt
Release date
2024-11-25
Shanghai UCHEM Inc.
Product
Tri-tert-butylphosphonium tetrafluoroborate 131274-22-1
Price
US $12.00-260.00/g
Min. Order
25g
Purity
0.98
Supply Ability
25kg
Release date
2023-10-26

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