4706-17-6

Usage

Uses

Used in Pharmaceutical Industry:
TRIS(HYDROXYPROPYL)PHOSPHINE is used as a reducing agent for the cleavage of disulfide bonds in both aqueous and buffered aqueous-organic medium. This application is crucial in the development and synthesis of various pharmaceutical compounds, as disulfide bonds play a significant role in the structure and stability of proteins and peptides.
Used in Chemical Synthesis:
TRIS(HYDROXYPROPYL)PHOSPHINE is used as a ligand in the synthesis of dendritic macromolecules, which are used as catalysts in heterogenizing homogeneous reactions. Dendritic macromolecules are highly branched structures that have a wide range of applications in catalysis, drug delivery, and sensing due to their unique properties and ability to accommodate multiple functional groups.
Used in Peptide Synthesis:
TRIS(HYDROXYPROPYL)PHOSPHINE is used as a reducing agent for the synthesis of disulfide cyclopeptides via one-pot peptide ligation-oxidative cyclization. This application is essential in the development of cyclic peptides, which have a wide range of biological activities and are used in various therapeutic applications, including antibiotics, antifungals, and anticancer agents.

Synthetic route

acetic acid 3-[bis-(3-acetoxy-propyl)-phosphanyl]-propyl ester → tris(3-hydroxypropyl)phosphine (4706-17-6) + tris(3-hydroxypropyl)phosphane oxide (51805-42-6)

Conditions	Yield
hydrolysis; Yield given; Yields of byproduct given;

allyl alcohol (107-18-6) + phosphine → (3-Hydroxypropyl)phosphan (4706-18-7) + bis-(3-hydroxy-propyl)-phosphine (4706-16-5) + tris(3-hydroxypropyl)phosphine (4706-17-6)

Conditions	Yield
im UV-Licht;

allyl alcohol (107-18-6) → tris(3-hydroxypropyl)phosphine (4706-17-6) + bis-<3-hydroxy-propyl>-phosphine;3-phosphino-propan-1-ol

Conditions	Yield
With phosphan Irradiation.UV-Bestrahlung;

trimethyl 3,3',3''-phosphanetriyltripropionate (29269-17-8) → tris(3-hydroxypropyl)phosphine (4706-17-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h;

bis(dimethylamino)dimethylsilane (3768-58-9) + tris(3-hydroxypropyl)phosphine (4706-17-6) → [(3-{bis-[3-(dimethylamino-dimethyl-silanyloxy)-propyl]-phosphanyl}-propoxy)-dimethyl-silanyl]-dimethyl-amine

Conditions	Yield
In tetrahydrofuran	91%

n-Butyl chloride (109-69-3) + tris(3-hydroxypropyl)phosphine (4706-17-6) → butyltris(3-hydroxypropyl)phosphonium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 16h;	90%

tris(3-hydroxypropyl)phosphine (4706-17-6) + p-benzoquinone (106-51-4) → C15H25O5P

Conditions	Yield
In acetone at 20℃; Inert atmosphere;	86%

tris(3-hydroxypropyl)phosphine (4706-17-6) + 4-Vinylbenzyl chloride (1592-20-7) → tris(hydroxypropyl)(4-vinylbenzyl)phosphonium chloride

Conditions	Yield
In acetonitrile at 80℃; for 24h; Inert atmosphere;	82%
In acetonitrile for 16h; Inert atmosphere; Heating;	79%

tris(3-hydroxypropyl)phosphine (4706-17-6) + 2-methoxy-1,4-benzoquinone (2880-58-2) → C16H27O6P

Conditions	Yield
In acetone at 20℃; Inert atmosphere;	81%

(η(5)-C5Me5)Ru(CO)2Cl + tris(3-hydroxypropyl)phosphine (4706-17-6) → (C5(CH3)5)RuCl(CO)(P((CH2)3OH)3) (217815-52-6)

Conditions	Yield
In not given Irradiation (UV/VIS); Ar-atmosphere; in THF or MeOH/H2O, not specified; stirring and irradiating equimolar amts. for 1 h in quartz autoclave, then refluxing; solvent removal (vac.), chromy. (SiO2, ether, then ethyl acetate/MeOH=4:1), solvent removal (vac.), washing (H2O), drying, recrystn. (hot MePh); elem. anal.;	78%

tris(3-hydroxypropyl)phosphine (4706-17-6) + coniferaldehyde (20649-42-7, 458-36-6) → C19H31O6P

Conditions	Yield
In acetone at 20℃; for 3h;	78%

tris(3-hydroxypropyl)phosphine (4706-17-6) → tris(3-bromopropyl)phosphine (1309945-96-7)

Conditions	Yield
With phosphorus tribromide In dichloromethane at 20℃; for 18h;	73%
With phosphorus tribromide In dichloromethane at 20℃; for 18h; Inert atmosphere;	29%

tris(3-hydroxypropyl)phosphine (4706-17-6) + sinapinaldehyde (4206-58-0, 87345-53-7) → C20H33O7P (958644-05-8)

Conditions	Yield
In acetone at 20℃; for 3h;	70%

tris(3-hydroxypropyl)phosphine (4706-17-6) + [(3-{bis-[3-(dimethylamino-dimethyl-silanyloxy)-propyl]-phosphanyl}-propoxy)-dimethyl-silanyl]-dimethyl-amine → 3-[{3-[(3-{bis-[3-({3-[bis-(3-hydroxy-propyl)-phosphanyl]-propoxy}-dimethyl-silanyloxy)-propyl]-phosphanyl}-propoxy)-dimethyl-silanyloxy]-propyl}-(3-hydroxy-propyl)-phosphanyl]-propan-1-ol

Conditions	Yield
In tetrahydrofuran

Upstream product

• 107-18-6 allyl alcohol 
• 29269-17-8 trimethyl 3,3',3''-phosphinetriyltripropanoate 

Downstream Products

• 958644-05-8 C₂₀H₃₃O₇P 
• 1445780-86-8 C₁₈H₂₉O₅P 
• 1445780-96-0 C₉H₇O₂^(1-)*C₁₈H₃₀O₅P⁽¹⁺⁾*C₉H₂₁O₃P 
• 1445780-87-9 C₁₈H₂₉O₆P 
• 1445780-88-0 C₁₈H₂₉O₆P 
• 1445780-89-1 C₁₈H₂₉O₆P 
• 1445780-90-4 C₂₀H₃₃O₇P 
• 1445780-91-5 C₁₉H₃₁O₇P 
• 1445780-92-6 C₁₈H₂₉O₇P 
• 1445780-93-7 C₂₀H₃₃O₈P 

Relevant academic research and scientific papers

NOVEL CYTOTOXIC AGENTS FOR CONJUGATION OF DRUGS TO CELL BINDING MOLECULE

Provided are cytotoxic agents, pyrrolo[2,1-c][1,4]benzodiazepine (PBD) derivatives, their conjugates with a cell-binding agent, the preparation and the therapeutic uses in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.

Selective two-phase-hydrogenation of sorbic acid with novel water soluble ruthenium complexes

Neutral and cationic water soluble Cp*-ruthenium-complexes of the type [Cp*Ru(CO)Cl(PR3)] and [Cp*Ru(CO)(PR3)]CF3SO3 (R=CH2OH, (CH2)3OH, Ph-m-SO3Na) have been synthesized for the first time and have been used as catalysts in two-phase-hydrogenations. The neutral complexes have been fully characterized. But the cationic complexes which have not been isolated are effective catalysts for the selective hydrogenation of sorbic acid in water/n-heptane leading to the formation of cis-3-hexenoic acid and trans-3-hexenoic acid.