4706-17-6

Basic information

• Product Name: TRIS(HYDROXYPROPYL)PHOSPHINE
• Synonyms: TRI(HYDROXYPROPYL)PHOSPHINE;TRIS(HYDROXYPROPYL)PHOSPHINE;tris(3-Hydroxypropyl)phosphine;TRIS(HYDROXYPROPYL)PHOSPHINE, MIN. 80%;Tris(hydroxypropyl)phosphine,min.80%;HISHICOLIN P-540;3,3',3''-(Phosphinetriyl)tris(1-propanol);3,3',3''-Phosphinetriyltris(1-propanol)
• CAS NO: 4706-17-6
• Molecular Formula: C₉H₂₁O₃P
• Molecular Weight: 208.24
• Product Categories: Tertiary Phosphines;organophosphorus ligand;Achiral Phosphine;Alkyl Phosphine
• Mol File: 4706-17-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 196-198 °C(Press: 1 Torr)
• Flash Point: >110℃
• Appearance: viscous/liquid
• Density: 1.136 g/mL at 25 °C
• Storage Temp.: +2C to +8C
• PKA: 14.59±0.10(Predicted)
• Sensitive: air sensitive
• CAS DataBase Reference: TRIS(HYDROXYPROPYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(HYDROXYPROPYL)PHOSPHINE(4706-17-6)
• EPA Substance Registry System: TRIS(HYDROXYPROPYL)PHOSPHINE(4706-17-6)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-36-27
• RIDADR: 2924
• WGK Germany: 3
• Hazardous Substances Data: 4706-17-6(Hazardous Substances Data)

Usage

Uses

Tris(hydroxypropyl)phosphine can be used as a:Reducing agent for the cleavage of disulfide bonds in both aqueous and buffered aqueous-organic medium.Ligand in the synthesis of dendritic macromolecules which are used as catalysts in heterogenizing homogeneous reactions.Reducing agent for the synthesis of disulfide cyclopeptides via one-pot peptide ligation-oxidative cyclization.

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

• 1520095-49-1 C₁₉H₃₁O₅P 
• 1520095-40-2 C₂₁H₃₅⁽²⁾HO₆P⁽¹⁺⁾*C⁽²⁾H₃O^(1-) 
• 1445780-93-7 C₂₀H₃₃O₈P 
• 1445780-92-6 C₁₈H₂₉O₇P 
• 1445780-91-5 C₁₉H₃₁O₇P 
• 1445780-90-4 C₂₀H₃₃O₇P 
• 1445780-89-1 C₁₈H₂₉O₆P 
• 1445780-88-0 C₁₈H₂₉O₆P 
• 1445780-87-9 C₁₈H₂₉O₆P 

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