63995-70-0

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 NO: 63995-70-0
• Molecular Formula: C₁₈H₁₂Na₃O₉PS₃
• Molecular Weight: 568.42
• EINECS: 264-596-6
• Product Categories: organophosphorus ligand;Building Blocks;Catalysis and Inorganic Chemistry;Chemical Synthesis;New Products for Chemical Synthesis;Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds;Phosphines
• Mol File: 63995-70-0.mol
• Article Data: 10

Chemical Properties

• Appearance: white to off-white/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Water (Slightly)
• Water Solubility: Soluble in water.
• Stability: Hygroscopic
• BRN: 3584807
• CAS DataBase Reference: Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt(63995-70-0)
• EPA Substance Registry System: Triphenylphosphine-3,3',3''-trisulfonic acid trisodium salt(63995-70-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 1
• F: 10
• Hazardous Substances Data: 63995-70-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Uses

Tris(3-sulfophenyl)phosphine Trisodium Salt is a reagent used in organic synthesis such as benzothiazole-based cycloplatinated chromophores.

InChI:InChI=1/C18H15O9PS3.3Na/c19-29(20,21)16-7-1-4-13(10-16)28(14-5-2-8-17(11-14)30(22,23)24)15-6-3-9-18(12-15)31(25,26)27;;;/h1-12H,(H,19,20,21)(H,22,23,24)(H,25,26,27);;;/q;3*+1/p-3

Synthetic route

triphenylphosphine (603-35-0) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
Stage #1: triphenylphosphine With chlorosulfonic acid; sulfuric acid at 0 - 25℃; Stage #2: With sodium hydroxide In water at 60℃; Temperature; Reagent/catalyst;	98.6%
Stage #1: triphenylphosphine With oleum at 0 - 20℃; for 150h; Stage #2: With sodium hydroxide In water	66%
With sulfuric acid for 168h; Ambient temperature;	11%

tris (3-ethyl phenyl sulfonate) phosphine (135265-27-9) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With sodium bromide In water; acetone for 48h; Ambient temperature;	66%

carbonyl(hydrido)tris{tris(sodium-m-sulphonatophenyl)phosphine}rhodium(I)-nonahydrate → trans-carbonyl(hydroxy)bis{tris(sodium-m-sulphonatophenyl)phosphine}rhodium(I)-hexahydrate + trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
In water byproducts: H2; (N2 or Ar); refluxing (12 h, vac.); chromy. (Sephadex); elem. anal.;	A 63% B n/a

tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With HSiCl

C18H18N3O6PS3 → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With sodium hydroxide

C21H24N3O6PS3 → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With sodium hydroxide

C24H30N3O6PS3 → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With sodium hydroxide

disodium P-phenyl-3,3'-phosphinediyl-bis(benzenesulfonate) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
With sodium hydroxide; sulfuric acid for 48h; Ambient temperature;

triphenylphosphine (603-35-0) + thiocyanato → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ClSO3H 3: NaOH View Scheme
Multi-step reaction with 3 steps 1: ClSO3H 2: NH3 3: NaOH View Scheme
Multi-step reaction with 3 steps 1: ClSO3H 3: NaOH View Scheme

C18H12Cl3O6PS3 (345650-44-4) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: NH3 2: NaOH View Scheme
Multi-step reaction with 2 steps 2: NaOH View Scheme

tris (3-sulfonatophenyl) phosphine oxide, triacid (96723-93-2) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Ag2CO3, aq. aerosol OT / 1.) 25 deg C, 24 h, 2.) toluene, reflux, 24 h 2: 89 percent / SiHCl3 / toluene; tetrahydrofuran / 22 h / Heating 3: 66 percent / sodium bromide / H2O; acetone / 48 h / Ambient temperature View Scheme

tris (3-ethyl phenyl sulfonate) phosphine oxide (135265-26-8) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / SiHCl3 / toluene; tetrahydrofuran / 22 h / Heating 2: 66 percent / sodium bromide / H2O; acetone / 48 h / Ambient temperature View Scheme

Pt(P(C6H4SO3Na)3)3 → [Pt(μ-OH)(P(m-C6H4SO3Na)3)2]2(2+) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
In water pH 13; detected by NMR spectra;

Pt(H)(P(C6H4SO3Na)3)3(1+)*Cl(1-)*CH3NO2=PtH(P(C6H4SO3Na)3)3Cl*CH3NO2 → trans-[PtCl(H)(P(m-C6H4SO3Na)3)2] + trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
In dimethyl sulfoxide detected by NMR spectra;

Pd(tris(3-sodium-sulfonatophenyl)phosphane)3 → Pd(bis(m-sulfophenyl)phosphine trisodium salt)3 + trisodium tris(3-sulfophenyl)phosphine (63995-70-0)

Conditions	Yield
In water dilute medium; detected by (13)P NMR spectra;	A 0% B 0%

triphenylphosphine (603-35-0) → trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + disodium P-phenyl-3,3'-phosphinediyl-bis(benzenesulfonate)

Conditions	Yield
Stage #1: triphenylphosphine With sulfuric acid; sulfur trioxide at 25 - 30℃; for 21h; Inert atmosphere; Stage #2: With sodium hydroxide In water Inert atmosphere;

poly(methacrylic acid) (79-41-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H18O11PS3(3-)*3Na(1+) (115524-87-3)

Conditions	Yield
In water	100%

poly(methacrylic acid) (79-41-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H17(2)HO11PS3(3-)*3Na(1+) (115524-88-4)

Conditions	Yield
With water-d2	100%

(E)-but-2-enoic acid (107-93-7) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H18O11PS3(3-)*3Na(1+) (115524-91-9)

Conditions	Yield
In water at 50℃;	100%

(E)-but-2-enoic acid (107-93-7) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H17(2)HO11PS3(3-)*3Na(1+) (115524-92-0)

Conditions	Yield
With water-d2 at 50℃;	100%

2-methylenesuccinic acid (97-65-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C23H18O13PS3(3-)*3Na(1+) (115524-89-5)

Conditions	Yield
In water	100%

2-methylenesuccinic acid (97-65-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C23H17(2)HO13PS3(3-)*3Na(1+) (115524-90-8, 122865-77-4)

Conditions	Yield
With water-d2	100%

trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2)

Conditions	Yield
With dihydrogen peroxide In water for 3h; Ambient temperature;	100%
With dihydrogen peroxide In water Heating;	100%

trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + acrylic acid (79-10-7) → C21H16O11PS3(3-)*3Na(1+) (115524-85-1)

Conditions	Yield
In water	100%

trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + acrylic acid (79-10-7) → C21H15(2)HO11PS3(3-)*3Na(1+) (115524-86-2)

Conditions	Yield
With water-d2	100%

Ru6C*17CO = [Ru6C(CO)17] + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 3Na(1+)*Ru6(C)*16CO*P(C6H4SO3)3(3-)=Ru6(C)(CO)16(P(C6H4SO3Na)3)

Conditions	Yield
In methanol N2-atmosphere; refluxing (2 h); evapn. (reduced pressure), washing (hexane), drying (vac.);	100%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 3Na(1+)*Ru3(CO)11(P(C6H4SO3)3)(3-)=Ru3(CO)11(P(C6H4SO3Na)3)

Conditions	Yield
In methanol N2-atmosphere, molar ratio = 1 : 1; refluxing (2 h); evapn. (reduced pressure), washing (hexane), drying (vac.);	100%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 6Na(1+)*Ru3(CO)10(P(C6H4SO3)3)2(6-)=Ru3(CO)10(P(C6H4SO3Na)3)2

Conditions	Yield
In methanol N2-atmosphere, molar ratio = 1 : 2; refluxing (2 h); evapn. (reduced pressure), washing (hexane), drying (vac.);	100%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 9Na(1+)*Ru3(CO)9(P(C6H4SO3)3)3(9-)=Ru3(CO)9(P(C6H4SO3Na)3)3

Conditions	Yield
In methanol N2-atmosphere, molar ratio = 1 : 3; refluxing (2 h); evapn. (reduced pressure), washing (hexane), drying (vac.);	100%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → Au(sodiumtriphenylphosphine-3,3',3''-trisulfonate)Cl

Conditions	Yield
In water; acetonitrile at 20℃; for 2h; Inert atmosphere;	100%
In dichloromethane; water; acetone ligand in acetone and 9 drops of H2O added dropwise to soln. of 1 equiv.of Au complex in CH2Cl2, stirred at room temp. for 30 min; evapd.(vac.), pptd.(acetone/Et2O 1:2 v/v), filtered (vac.), elem. anal.,;	99%

bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (35138-22-8) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C44H32O18P2RhS6(5-)*6Na(1+)*BF4(1-)

Conditions	Yield
In water at 20℃; for 0.166667h;	100%

potassium tetrachloroplatinate(II) (10025-99-7) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → [Pt(tris(3-sulfonatophenyl)phosphane sodium salt)3Cl]Cl

Conditions	Yield
In water-d2 at 25℃; for 0.25h; Inert atmosphere;	100%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → sodium tris(tris(m-sulphonatophenyl)phosphine)gold(I)

Conditions	Yield
In dichloromethane; water salt of ligand (3 equiv.) in H2O was added to stirred soln. of Au complex (1 equiv.) in CH2Cl2; mixt. was stirred for 5 h; evapd. (vac.); H2O added to residue; filtered; solvent removed (vac.);	99%

[Pt2(6,6'-diphenyl-2,2'-bipyridine(-4H))(DMSO)2] + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + water (7732-18-5) → [Pt2(6,6'-diphenyl-2,2'-bipyridine(-4H))(P(m-PhSO3Na)3)2]*6H2O

Conditions	Yield
In water; acetone Pt complex was added with stirring to soln. of ligand in H2O/acetone (1/1) under Ar; mixt. was stirred at room temp. for 15 h; filtered; concd.; treated with acetone; filtered; washed (acetone); elem. anal.;	99%

Phenylpropargyl aldehyde (2579-22-8) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → (E)-3-phenylpropenal (14371-10-9) + tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2)

Conditions	Yield
In water Ambient temperature;	A 98% B n/a

fac-triaquatricarbonyltechnetium-99m(1+) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + C64H82N20O16S4Zn → C53H53N10O20PS5(99)Tc(3-)*3Na(1+)

Conditions	Yield
at 40 - 65℃; for 0.416667h; Inert atmosphere; Schlenk technique;	98%

chloro(1,5-cyclooctadiene)iridium(I) dimer + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → chloro(η4-1,5-cyclooctadiene)bis{tris(sodium-m-sulphonatophenyl)phosphine}iridium-hexahydrate

Conditions	Yield
In water; toluene (N2 or Ar); addn. of org. compd. in H2O to Ir-complex in toluene with stirring (room temp.), stirring (15 min); phase sepn., extn. org. phase (H2O), washing aq. phases (toluene), evapn. (vac.), chromy. (Sephadex); elem. anal.;	97%

Phenylpropargyl aldehyde (2579-22-8) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2) + trans-<α,β-2H2>cinnamaldehyde (130947-27-2)

Conditions	Yield
In water-d2 Ambient temperature;	A n/a B 96%

potassium tetrachloroplatinate(II) (10025-99-7) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → cis-dichlorobis{tris(sodium-m-sulphonatophenyl)phosphine}platinum-hexahydrate

Conditions	Yield
In water byproducts: KCl; (N2 or Ar); dropwise addn. of Pt-complex in H2O to org. compd. in H2O (room temp.), stirring (20 h); solvent evapn. (vac.);	96%

(1,5-cyclooctadiene)dimethylplatinum(II) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + dimethyl sulfoxide (67-68-5) → cis-PtMe2(TPPTS)2*DMSO

Conditions	Yield
In dimethyl sulfoxide Pt-complex was mixed with ligand under N2, sealed, evacuated, DMSO was added, stirred for 18 h at room temp., CH2Cl2 was added; vac. filtered, washed with CH2Cl2 and Et2O, dried in vac. at 80°Cfor 24 h; elem. anal.;	96%

bis(dimethylgold(III) iodide) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + water (7732-18-5) → cis-Me2AuI(3,3',3''-phosphinidynetris(benzenesulfonic acid) trisodium salt)*5H2O

Conditions	Yield
In water; acetone 2 equiv. of P-compd., 0 °C; pptg. with acetone, recrystn.from MeOH-acetone, elem. anal.;	96%

bis(dimethylgold(III) iodide) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + water (7732-18-5) → [cis-Me2Au(3,3',3''-phosphinidynetris(benzenesulfonic acid) trisodium salt)2]I*5H2O

Conditions	Yield
In water; acetone 2 equiv. of P-compd., 0 °C, further addn. of 2 equiv. of P-compd.; pptg. with acetone, recrystn. from MeOH-acetone, elem. anal.;	96%
In water; acetone 4 equiv. of P-compd., 0 °C; pptg. with acetone, recrystn.from MeOH-acetone, elem. anal.;	96%

C98H199N3O16*CH4O3S + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 3C98H199N3O16*C18H15O9PS3

Conditions	Yield
In acetonitrile at 20℃; for 72h; Inert atmosphere; Schlenk technique;	96%

C90H183N3O42*CH4O3S + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → 3C90H183N3O42*C18H15O9PS3

Conditions	Yield
In acetonitrile at 20℃; for 72h; Inert atmosphere; Schlenk technique;	96%

fac-triaquatricarbonyltechnetium-99m(1+) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) + C64H82N20O12S4Zn → C53H53N10O18PS5(99)Tc(3-)*3Na(1+)

Conditions	Yield
at 40 - 65℃; for 0.416667h; Inert atmosphere; Schlenk technique;	96%

Upstream product

• 603-35-0 triphenylphosphine 
• 96723-93-2 tris (3-sulfonatophenyl) phosphine oxide, triacid 
• 345650-44-4 C₁₈H₁₂Cl₃O₆PS₃ 
• 135265-27-9 tris (3-ethyl phenyl sulfonate) phosphine 
• 98511-67-2 tris(natrium-m-sulfonatophenyl)phosphanoxid 
• 135265-26-8 tris (3-ethyl phenyl sulfonate) phosphine oxide 

Downstream Products

• 24461-32-3 2,3-[²H₂]-fumaric acid 
• 98511-67-2 tris(natrium-m-sulfonatophenyl)phosphanoxid 
• 122570-50-7 (1,2-dicarboxyethenyl)tris(3-sulfophenyl)phosphonium inner salt, trisodium salt 
• 122570-50-7 (1,2-dicarboxyethenyl)tris(3-sulfophenyl)phosphonium inner salt, trisodium salt 
• 122570-53-0 (1,2-dicarboxyethenyl-2-d)tris(3-sulfophenyl)phosphonium inner salt, trisodium salt 
• 122570-53-0 (1,2-dicarboxyethenyl-2-d)tris(3-sulfophenyl)phosphonium inner salt, trisodium salt 
• 110-17-8 (2E)-but-2-enedioic acid 
• 3469-20-3 2,3-diphenyl-1H-indole 

Relevant articles and documents

Heterolytic splitting of allylic alcohols with palladium(O)-TPPTS in water. Stabilities of the allylphosphonium salt of TPPTS and of the ionic complex [Pd(η-allyl)(TPPTS)2]+

The Pd(TPPTS)3 complex (TPPTS is the sodium salt of tris(m-sulfophenyl)phosphine) easily ionizes allyl alcohol in water over a wide range of pH: OH- and TPPTS are released, and [Pd(η3- allyl)(TPPTS)2]+ is formed. The released TPPTS further reacts with the palladium cationic complex to reversibly produce both the allylphosphonium salt of TPPTS [(allyl)Ar3P]+ and Pd(TPPTS)3, the latter acting as the catalyst of the allylation of TPPTS by allyl alcohol. Primary allylic alcohols, such as butenol (trans-2-buten-1ol), prenol (3-methyl-2-buten-1-ol), geraniol, and cinnamyl alcohol, react with Pd(TPPTS)3 to produce hydroxide ion, the corresponding hydrosoluble cationic palladium complex, and allylic phosphonium salts. At room temperature, [Pd(η3-allyl)(TPPTS) 2]+ is stable up to pH 12, but beyond this value, palladium precipitates. The temperature has an adverse effect on the complex stability: palladium precipitates at 80 °C, even at pH 7, with the formation of a small amount of propylene. The addition of [(allyl)Ar3P] + increases the stability of [Pd(η3-allyl)(TPPTS) 2]+. Above pH 10, [(allyl)Ar3P]+ decomposes into OTPPTS and propylene by reaction with OH. At lower pH, [(allyl)Ar3P]+ is slowly isomerized into [(propenyl)Ar3P]+, which further reduces its stability toward pH and temperature. These consecutive reactions of the TPPTS ligand could explain most of the catalyst instability. This study outlines the basis for a better understanding of the instability phenomenon of the catalytic system Pd(0)-TPPTS in reactions with allylic intermediates, e.g. the Tsuji-Trost reaction, and in the reaction of dienes in aqueous media in which palladium often precipitates.

Interconversion between platinum (II) and platinum (0) with change of pH: Aqueous reactions of Pt(H)(TPPTS)3+ (TPPTS = P(m-C6H4SO3Na)3)

The interconversion between platinum(II) and platinum(0) with change of pH was investigated. It was shown that the oxidation state for platinum complexes can be controlled through variation of the pH of an aqueous solution. As the pH was decreased in wate

METHOD FOR PRODUCING 2,7-OCTADIEN-1-OL

Provided is a simple and industrially advantageous method for producing 2,7-octadien-1-ol, in which an expensive palladium catalyst is recovered in high efficiency and the reaction rate per atom of palladium is enhanced. Specifically, provided is a method for producing 2,7-octadien-1-ol by subjecting butadiene and water to a telomerization in the presence of a palladium catalyst containing a water-soluble triarylphosphine having two or more sulfonate groups in the molecule and a palladium compound, a tertiary amine, and carbon dioxide, including a step of mixing the telomerization solution obtained by the telomerization with an organic solvent having a dielectric constant at 25° C. of 2 to 18, followed by carrying out phase separation in the presence of carbon dioxide, thereby obtaining 2,7-octadien-1-ol from an organic phase while recovering an aqueous phase including the palladium catalyst. By this production method, the selectivity for 2,7-octadien-1-ol is enhanced.