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Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt

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Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt Basic information

Product Name:
Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt
Synonyms:
  • TRI(M-SULFOPHENYL)PHOSPHINE, SODIUM SALT
  • TRIS(3-SULFONATOPHENYL) PHOSPHINE HYDRATE
  • TRIS(3-SULFONATOPHENYL)PHOSPHINE HYDRATE SODIUM SALT
  • TRIS(3-SULFONATOPHENYL) PHOSPHINE HYDRATE, TRISODIUM SALT
  • TRIS(3-SULFONATOPHENYL)PHOSPHINE TETRAHYDRATE, SODIUM SALT
  • TRIS(3-SULFOPHENYL)PHOSPHINE TRISODIUM SALT
  • TRIPHENYLPHOSPHINE-3,3',3''-TRISULFONIC ACID TRISODIUM SALT
  • 3,3',3''-PHOSPHINIDYNETRIS(BENZENESULFONIC ACID) TRISODIUM SALT
CAS:
63995-70-0
MF:
C18H16NaO9PS3
MW:
526.46
EINECS:
264-596-6
Product Categories:
  • Phosphines
  • organophosphorus ligand
  • Building Blocks
  • Catalysis and Inorganic Chemistry
  • Chemical Synthesis
  • New Products for Chemical Synthesis
  • Organic Building Blocks
  • Sulfonic/Sulfinic Acids
  • Sulfur Compounds
Mol File:
63995-70-0.mol
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Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt Chemical Properties

Melting point:
>300°C
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO (Slightly), Water (Slightly)
form 
Powder
color 
white to off-white
Water Solubility 
Soluble in water.
BRN 
3584807
Stability:
Hygroscopic
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
1
10
HS Code 
29319090

MSDS

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Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

Tris(3-sulfophenyl)phosphine Trisodium Salt (Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt) is a reagent used in organic synthesis such as benzothiazole-based cycloplatinated chromophores.

Preparation

Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) is synthesized by sulfonation of triphenylphosphine with oleum (i.e., concentrated H2SO4 and SO3). Various parameters (triphenylphosphine/oleum ratio,wt % of SO3, time, temperature, and agitation speed) have been studied and modified to suppress the formation of by-products such as phosphines with a low degree of sulfonation and phosphine oxides. One particularly attractive method employs orthoboric acid B(OH)3, concentrated H2SO4, and a controlled SO3 concentration and cleanly affords either disulfonated ligand (TPPDS) or TPPTS with negligible oxidation and no by-products.

Application

Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) can be used as a capping agent in the synthesis of TPPTS stabilized palladium nanoparticles (PdNPs) using K2PdCl4 as the palladium source and HCOONa as the reductant. The TPPTS stabilized PdNPs are applicable as an efficient catalyst in the aqueous phase Suzuki-Miyaura coupling reaction at room temperature. TPPTS is also a ligand in the metal-catalyzed hydroformylation of functionalized olefins and direct arylation polymerization reactions.

storage

Solid Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt (TPPTS) is substantially stable to air, but bottles of TPPTS should be flushed with N2 or Ar and kept tightly closed for prolonged storage. TPPTS is slowly oxidized to the phosphine oxide in the solution. Therefore, oxygen-free solvents are preferred.

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