Trioctylphosphine oxide supplier

Name
Trioctylphosphine oxide
EINECS 201-121-3
CAS No. 78-50-2
Article Data33
CAS DataBase
Density 0.861 g/cm³
Solubility insoluble in water
Melting Point 50-55°C
Formula C₂₄H₅₁OP
Boiling Point 408.842 °C at 760 mmHg
Molecular Weight 386.642
Flash Point 259.779 °C
Transport Information
Appearance white crystalline powder
Safety 26-36/39-39
Risk Codes 38-41
Molecular Structure
Hazard Symbols Xi
Synonyms Cyanex 921;Hostarex PX 324;TOPO;Tri-n-octylphosphine oxide;Trioctylphosphine oxide;
PSA 26.88000
LogP 9.43100

Synthetic route

: 4731-53-7
TOP

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With fluorosulfonylchloride In dichloromethane for 1h; Ambient temperature;	98%
Stage #1: TOP With water; dihydrogen peroxide In toluene at 0 - 20℃; for 12h; Inert atmosphere; Stage #2: In toluene at 20℃; for 4h; Molecular sieve;	90%
In 1,2,4-trimethylbenzene at 25℃; for 1h; Inert atmosphere;
With selenium; octadec-1-ene

: 111-87-5
octanol

: 7539-86-8
dioctylphosphinyl chloride

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
In chloroform at 50℃; for 2h;	95.1%

: C24H51BrClP

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With water In toluene at 20℃; for 1h;	92.6%

: 4731-53-7
TOP

: 22585-81-5
4-chlorophenylphosphonoyl dichloride

A: 78-50-2
cyanex-921

B: 1005-33-0
4-chlorophenyldichlorophosphine

Conditions

Conditions	Yield
In dichloromethane	A n/a B 84%

...Expand

: 111-66-0
oct-1-ene

: 3011-82-3
oxyde de dioctyl phosphine

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With acetic acid at 120 - 135℃; for 8h;	81.4%

: 111-85-3
1-Chlorooctane

: 3011-82-3
oxyde de dioctyl phosphine

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With sodium amide; tert-butyl alcohol In tetrahydrofuran at 40℃; for 0.833333h;	72%

: 106446-20-2
3-(4-chlorophenyl)-4-trioctylphosphiniminofurazan

A: 78-50-2
cyanex-921

B: 106446-23-5
azoxy(4-chlorophenylfurazan)

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 2h; Heating;	A n/a B 60%

: 111-85-3
1-Chlorooctane

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
In toluene; Petroleum ether	39%
With hydrogenchloride; trichlorophosphate In 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether; water

: 111-83-1
1-bromo-octane

A: 3011-82-3
oxyde de dioctyl phosphine

B: 78-50-2
cyanex-921

C: 6196-68-5
octylphosphinic acid

Conditions

Conditions	Yield
With potassium hydroxide semihydrate; phosphorus; N-benzyl-N,N,N-triethylammonium chloride In toluene at 60 - 62℃; for 5h; Reagent/catalyst; Inert atmosphere;	A n/a B n/a C 19%

...Expand

: 17049-49-9
octylmagnesium bromide

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With diethyl ether; trichlorophosphate
With trichlorophosphate

: 111-85-3
1-Chlorooctane

: 1779-48-2
phenylphosphinic acid

A: 78-50-2
cyanex-921

B: 2845-09-2
dioctyl(phenyl)phosphine oxide

Conditions

Conditions	Yield
With sodium hydroxide 1.) 200 deg C, 24 h, 2.) reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 111-85-3
1-Chlorooctane

: 107694-27-9
octylphenylphosphinous acid

A: 78-50-2
cyanex-921

B: 2845-09-2
dioctyl(phenyl)phosphine oxide

Conditions

Conditions	Yield
With sodium hydroxide 1.) 200 deg C, 24 h, 2.) reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 629-27-6
1-Iodooctane

A: 683-19-2
dioctylphosphinic acid

B: 78-50-2
cyanex-921

C: 1-methylheptyl-n-octylphosphinic acid

Conditions

Conditions	Yield
With phosphorus; iodine 1) 125 - 130 deg C, 36 h, 2) H2O; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 629-27-6
1-Iodooctane

A: 683-19-2
dioctylphosphinic acid

B: 78-50-2
cyanex-921

C: 1-methylheptyl-n-octylphosphinic acid

D: 128144-48-9
1-methylheptyl-di-n-octylphosphine oxide

Conditions

Conditions	Yield
With phosphorus; iodine 1) 150 - 160 deg C, 16 h, 2) H2O; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 111-83-1
1-bromo-octane

: 1779-48-2
phenylphosphinic acid

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With potassium hydroxide 1.) 200 deg C, 7.5 h, 2.) reflux, 4 h; Yield given. Multistep reaction;

: 111-83-1
1-bromo-octane

: 107694-27-9
octylphenylphosphinous acid

A: 78-50-2
cyanex-921

B: 2845-09-2
dioctyl(phenyl)phosphine oxide

Conditions

Conditions	Yield
With sodium hydroxide 1.) 200 deg C, 5 h, 2.) reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 111-83-1
1-bromo-octane

A: 3011-82-3
oxyde de dioctyl phosphine

B: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With phosphorus; potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran at 60 - 65℃; for 6h; Yield given;

: 106446-20-2
3-(4-chlorophenyl)-4-trioctylphosphiniminofurazan

A: 78-50-2
cyanex-921

B: 106446-22-4
3-(4-chlorophenyl)-4-nitrofurazan

C: 106446-23-5
azoxy(4-chlorophenylfurazan)

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 16h; Ambient temperature;

...Expand

octylmagnesium halide: octylmagnesium halide

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
With trichlorophosphate Alkylation;

: 126-73-8
phosphoric acid tributyl ester

: Th(NO3)4(tri-noctylphosphine oxide)2

A: 78-50-2
cyanex-921

B: Th(NO3)4(tributylphosphate)2

Conditions

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;

...Expand

: 126-73-8
phosphoric acid tributyl ester

: LaCl3(tri-noctylphosphine oxide)3

A: 78-50-2
cyanex-921

B: LaCl3(tributylphosphate)3

Conditions

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;

...Expand

: 67206-59-1
sodium dioctylphosphinate

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 16 h / 80 °C 2: chloroform / 2 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: chloroform / 16 h / 80 °C 2: water / chloroform 3: acetic acid / 8 h / 120 - 135 °C View Scheme
Multi-step reaction with 3 steps 1: chloroform / 16 h / 80 °C 2: toluene / 24 h / 100 °C 3: water / toluene / 1 h / 20 °C View Scheme

: 111-66-0
oct-1-ene

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hypophosphite; acetic acid / 4 h / 120 - 135 °C 2: chloroform / 16 h / 80 °C 3: chloroform / 2 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hypophosphite; acetic acid / 4 h / 120 - 135 °C 2: chloroform / 16 h / 80 °C 3: water / chloroform 4: acetic acid / 8 h / 120 - 135 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hypophosphite; acetic acid / 4 h / 120 - 135 °C 2: chloroform / 16 h / 80 °C 3: toluene / 24 h / 100 °C 4: water / toluene / 1 h / 20 °C View Scheme

: 7539-86-8
dioctylphosphinyl chloride

: 78-50-2
cyanex-921

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 24 h / 100 °C 2: water / toluene / 1 h / 20 °C View Scheme

: 127440-67-9, 127641-61-6
MoO2Br2(H2O)2

: 78-50-2
cyanex-921

: dioxomolybdenum(VI) dibromide bis(trioctyl phosphine oxide)

Conditions

Conditions	Yield
In diethyl ether mixed; evapd.(vac. room temp.), elem. anal.;	99%

: 78-50-2
cyanex-921

: 21741-98-0
3-amino-4-(p-chlorophenyl)-1,2,5-oxadiazole

: 106446-20-2
3-(4-chlorophenyl)-4-trioctylphosphiniminofurazan

Conditions

Conditions	Yield
With trifluoromethanesulfonic acid anhydride In dichloromethane 1.) -5 deg C, 0.5 h; 2.) -5 deg C, 3 h, then room temperature, overnight;	93%

: 78-50-2
cyanex-921

: 7722-84-1
dihydrogen peroxide

: molybdenum(VI) oxide

: [MoO(O2)2(OP(C8H17)3)]

Conditions

Conditions	Yield
In water suspending MoO3 in aq. H2O2 at 40°C for 4 h, addn. of the ligand,kept for 2 h; concn. (vac.), extn. (CH2Cl2), evapn., washing (H2O), drying (vac.); elem. anal.;	93%

...Expand

: uranyl(VI) nitrate

: 4173-74-4
1-Phenyl-3-methyl-4-acetyl-5-pyrazolon

: 78-50-2
cyanex-921

: UO2(C6H5NNCCH3CCOCH3CO)2(C8H17)3PO

Conditions

Conditions	Yield
In water; benzene UO2(NO3)2 soln. at pH 2 extd. with benzene soln. of PMAP and TOPO; benzene layer dried with Na2SO4, evapd. dryness in rotary evaporator and product recrystd. twice from n-hexane; elem. anal.;	89%

...Expand

: 78-50-2
cyanex-921

: lanthanide(III)chloride heptahydrate

: LaCl3(tri-noctylphosphine oxide)3

Conditions

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;	81.7%

: 78-50-2
cyanex-921

: [(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdCl(μ-Na)]2

: 1366181-66-9
[(κ2-P,O-2-(bis(2-methoxyphenyl)phosphino)benzenesulfonato)PdMe(OPOct3)]

Conditions

Conditions	Yield
With AgBF4 In dichloromethane byproducts: AgCl, NaBF4; using Schlenk techniques; stirring of suspn. of ((κ2-P,O-2-(2-MeOC6H4)2PC6H4SO3)PdCl(μ-Na))2 (0.5 equiv.), AgBF4 (1 equiv.) and OPOct3 (1 equiv.) in CH2Cl2 for 30 min in the dark; pptn., filtration, evapn., washing with pentane, drying under vac.; elem. anal.;	81%

: thorium(IV) nitrate pentahydrate

: 78-50-2
cyanex-921

: Th(NO3)4(tri-noctylphosphine oxide)2

Conditions

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;	80.8%

: europium(III) nitrate hexahydrate

: 78-50-2
cyanex-921

: 90076-65-6
bis(trifluoromethane)sulfonimide lithium

: [Eu(tri-n-octylphosphine oxide)4(NO3)2]bis(trifluoromethylsulfonyl)imide

Conditions

Conditions	Yield
Stage #1: cyanex-921; bis(trifluoromethane)sulfonimide lithium In ethanol at 60℃; Stage #2: europium(III) nitrate hexahydrate In ethanol; water at 60℃; for 4h;	76%

...Expand

: europium(III) nitrate pentahydrate

: 78-50-2
cyanex-921

: C22H13F3O2

: [Eu(TphTA)3]*TOPO*H2O

Conditions

Conditions	Yield
In ethanol at 20 - 50℃; for 21h;	75%

...Expand

: peroxotungstic acid

: 78-50-2
cyanex-921

: 185897-00-1
trioctylphosphine oxide-peroxotungstic acid

Conditions

Conditions	Yield
In 1,4-dioxane W compd. addn. to P-compd. soln. with stirring; oily phase sepn., washing (water, MeOH), solvent elimination (heating, 50°C, vac.), solidification (refrigerator); elem. anal.;	73%

: europium(III) nitrate pentahydrate

: 78-50-2
cyanex-921

: C22H13F3O2

: [Eu(TphTA)3]*2TOPO

Conditions

Conditions	Yield
In ethanol at 20 - 50℃; for 21h;	71%

...Expand

: europium(III) nitrate pentahydrate

: 78-50-2
cyanex-921

: C22H13F3O2

: [Eu(TphTA)2]*NO3*2TOPO

Conditions

Conditions	Yield
In ethanol at 20 - 50℃; for 21h;	68%

...Expand

: europium(III) nitrate pentahydrate

: 78-50-2
cyanex-921

: 893-33-4
4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione

: (nitrato)bis{trioctylphosphine oxide}bis{4,4,4-trifluoro-1-(2-naphthyl)butane-1,3-dionato}-europium(III)

Conditions

Conditions	Yield
In ethanol; water addition of 0.05 g Eu salt (as nitrate hydrate) in H2O (10 ml) to 0.08 g of the dione and 0.078 g of the phosphine oxide in 10 ml ethanol and solvation of the precipitate by addition of ethanol with stirring;; crystallization on standing in a beaker overnight; elem. anal., detn. by (1)H NMR-, IR spectroscopy, X-ray diffraction;;	60%

...Expand

: diammonium cerium(IV) nitrate

: 78-50-2
cyanex-921

: Ce(NO3)4(Oct3PO)2

Conditions

Conditions	Yield
In chloroform-d1 Solvent;	60%

: 78-50-2
cyanex-921

: 4731-53-7
TOP

Conditions

Conditions	Yield
With pinacolboronic acid In acetonitrile at 100℃; for 120h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;	57%
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 10h;
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; for 18h; Inert atmosphere; Sealed tube;

: 148509-02-8
(meso-5,10,15,20-tetra-p-tolylporphyrinato)Ti(η2-3-hexyne)

: 78-50-2
cyanex-921

: 326474-31-1
(meso-5,10,15,20-tetra-p-tolylporphyrinato)bis(trioctylphosphine oxide)Ti

Conditions

Conditions	Yield
In toluene byproducts: 3-hexyne; under N2; Ti complex and 2 equiv. of ligand in toluene stirred for 2.5 h; concd.; redissolved in hexanes; reduced in vac.; cooled to -25°C for 1 d; elem. anal.;	52%

: 78-50-2
cyanex-921

: 1109-15-5
tris(pentafluorophenyl)borate

: 356074-07-2
B(C6F5)3(C8H17)3PO

Conditions

Conditions	Yield
In pentane (N2); addn. of 1 equiv. of boron compd. to a soln. of phosphine in pentane; elem. anal.;	51%

: titanium tetra-n-propoxide

: 78-50-2
cyanex-921

: 7550-45-0
titanium tetrachloride

: titanium(IV) oxide

Conditions

Conditions	Yield
In further solvent(s) byproducts: ClCH(CH3)2; addn. of phosphine oxide to soln. of Ti-halide in heptadecane, heating (N2-atmosphere, 300°C), rapid addn. of 1 equiv. of Ti-alkoxide, 5 min; centrifugation, washing (acetone); XRD pattern characterisation;	50%

...Expand

: titanium tetra-n-propoxide

: 78-50-2
cyanex-921

: 7789-68-6
titanium(IV) bromide

: titanium(IV) oxide

Conditions

Conditions	Yield
In further solvent(s) byproducts: BrCH(CH3)2; addn. of phosphine oxide to soln. of Ti-halide in heptadecane, heating (N2-atmosphere, 300°C), rapid addn. of 1 equiv. of Ti-alkoxide, 5 min; centrifugation, washing (acetone); XRD pattern characterisation;	50%

...Expand

: titanium tetra-n-propoxide

: 78-50-2
cyanex-921

: 7783-63-3
titanium(IV) fluoride

: titanium(IV) oxide

Conditions

Conditions	Yield
In further solvent(s) byproducts: FCH(CH3)2; addn. of phosphine oxide to soln. of Ti-halide in heptadecane, heating (N2-atmosphere, 300°C), rapid addn. of 1 equiv. of Ti-alkoxide, 5 min; centrifugation, washing (acetone); XRD pattern characterisation;	50%

...Expand

: titanium tetra-n-propoxide

: 78-50-2
cyanex-921

: 7720-83-4
titanium(IV) iodide

: rutile

Conditions

Conditions	Yield
In further solvent(s) byproducts: ICH(CH3)2; addn. of phosphine oxide to soln. of Ti-halide in heptadecane, heating (N2-atmosphere, 300°C), rapid addn. of 1 equiv. of Ti-alkoxide, 5 min; centrifugation, washing (acetone); XRD pattern characterisation;	50%

...Expand

: 78-50-2
cyanex-921

: europium(III) chloride hexahydrate

: 1-phenyl-3-[4-(4-propylcyclohexyl)phenyl]propane-1,3-dione

: C120H183EuO8P2

Conditions

Conditions	Yield
With potassium hydroxide In ethanol	43%

...Expand

Trioctylphosphine oxide Specification

The IUPAC name of Tri-n-octylphosphine oxide is 1-Dioctylphosphoryloctane. With the CAS registry number 78-50-2, it is also named as Trioctyl phosphine oxide. The product's category is Phosphine Oxides and Sulfides, and the other registry number is 129406-23-1. Besides, it is white crystalline powder, which should be stored in closed, cool and dry place. In addition, this chemical is stable and incompatible with strong oxidizing agents, but insoluble in water.

The other characteristics of this product can be summarized as: (1)EINECS: 201-121-3; (2)ACD/LogP: 10.25; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): 10.251; (5)ACD/LogD (pH 7.4): 10.251; (6)ACD/BCF (pH 5.5): 1000000; (7)ACD/BCF (pH 7.4): 1000000; (8)ACD/KOC (pH 5.5): 8984523; (9)ACD/KOC (pH 7.4): 8984523; (10)H bond acceptors: 1; (11)H bond donors: 0; (12)Freely Rotating Bonds: 21; (13)Index of Refraction: 1.448; (14)Molar Refractivity: 120.111 cm³; (15)Molar Volume: 448.845 cm³; (16)Surface Tension: 30.999 dyne/cm; (17)Density: 0.861 g/cm³; (18)Flash Point: 259.779 °C; (19)Melting point: 50-55 °C; (20)Enthalpy of Vaporization: 63.523 kJ/mol; (21)Boiling Point: 408.842 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Tri-n-octylphosphine oxide: this chemical can be prepared by Trioctylphosphane.

This reaction needs sulfuryl chloride fluoride and CH₂Cl₂ at ambient temperature. The reaction time is 1 hour. The yield is 98 %.

Uses of Tri-n-octylphosphine oxide: this chemical is used as extracting agent and solvent. And it also can react with 4-(4-Chloro-phenyl)-furazan-3-ylamine to get 3-(4-Chlorophenyl)-4-trioctylphosphiniminofurazan.

This reaction needs Trifluoromethanesulfonic anhydride and CH₂Cl₂ at temperature of -5 °C for 0.5 h. The yield is 93 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to skin. And it is also risk of serious damage to the eyes. You should wear suitable protective clothing. and eye / face protection. Moreover, in case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC
(2)InChI:InChI=1/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3
(3)InChIKey:ZMBHCYHQLYEYDV-UHFFFAOYAY
(4)Std. InChI:InChI=1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3
(5)Std. InChIKey:ZMBHCYHQLYEYDV-UHFFFAOYSA-N

The toxicity data is as follows:

1.		skn-rbt 500 µL/24H MOD		NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0534743 .
2.		eye-rbt 100 mg/24H SEV		NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0572000 .

Product Name

Trioctylphosphine oxide

Synthetic route

Trioctylphosphine oxide Specification

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