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Trioctylphosphine

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Name

Trioctylphosphine

EINECS 225-234-2
CAS No. 4731-53-7 Density 0.831g/mLat 25°C(lit.)
PSA 13.59000 LogP 9.54980
Solubility Immiscible with water. Melting Point -60oC
Formula C24H51P Boiling Point 445 °C at 760 mmHg
Molecular Weight 370.64 Flash Point 236 °C
Transport Information UN 1760 8/PG 2 Appearance clear liquid
Safety 26-36/37/39-45 Risk Codes 34-36/37/38
Molecular Structure Molecular Structure of 4731-53-7 (Phosphine, trioctyl-) Hazard Symbols CorrosiveC, IrritantXi
Synonyms

NSC 102529;Tri-n-octylphosphine;

 

Trioctylphosphine Synthetic route

24219-37-2

di-n-octylmagnesium

Conditions
ConditionsYield
With phosphorus trichloride; iron(III)-acetylacetonate In tetrahydrofuran; n-heptane for 0.5h; Heating;85%
With phosphorus trichloride84%
78-50-2

cyanex-921

Conditions
ConditionsYield
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;
111-66-0

oct-1-ene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); phosphan at 80 - 100℃; for 6h;
62779-16-2

(Methoxycarbonylamino-methyl)-trioctyl-phosphonium; chloride

Conditions
ConditionsYield
With sodium methylate In methanol; diethyl ether
111-83-1

1-bromo-octane

Conditions
ConditionsYield
With iodine; magnesium; phosphorus trichloride 1.) ether, reflux, 15 min.; 2.) reflux, 96 h.; Yield given. Multistep reaction;
dichloro-trioctyl-phosphorane

dichloro-trioctyl-phosphorane

Conditions
ConditionsYield
With sodium
111-83-1

1-bromo-octane

sodium-compound of dioctyl phosphine

sodium-compound of dioctyl phosphine

lead(II) oleate

20612-73-1

trioctylphosphane selenide

A

lead(II) selenide

Conditions
ConditionsYield
In further solvent(s) byproducts: tri-n-octylphosphine oxide, oleate anhydride; (C8H17)3PSe injected into soln. of Pb compd. in 1-octadecene; nanocrystals grown at 170°C over 40 min; monitored by (31)P NMR spectra;A n/a
B 0%
616-38-6

carbonic acid dimethyl ester

1204316-79-9

1,1,1-trioctyl-1-methylphosphonium methylcarbonate

Conditions
ConditionsYield
In methanol at 140℃; for 20h; Inert atmosphere; Autoclave;100%
In methanol at 140℃; for 24h; Inert atmosphere; Autoclave;100%
In methanol at 150℃;100%
1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

Ni(COD)(tri-n-octylphosphine)2

Conditions
ConditionsYield
In toluene Ni complex reacted with 2 equiv. of tri-n-octylphosphine in toluene;99%

tetrakis(acetonitrile)copper(I)tetrafluoroborate

1264748-06-2

6,6’-diformyl-3,3’-bipyridine

106-50-3

1,4-phenylenediamine

([(H2NC6H4NCH(C5H3N)(C5H3N)CHNC6H4NH2)][Cu(trioctylphosphine)2]2[B(fluoride)4]2)

Conditions
ConditionsYield
In dimethyl sulfoxide byproducts: H2O; under inert atm. mixing (H2NC6H4)2, (CHOC5H3N)2, Cu complex, soln. of P compd. in DMSO, sealing, storage at 80°C (12 h);99%
7766-50-9

1-undecen-11-ylbromide

1412455-62-9

trioctyl(undec-10-enyl)phosphonium bromide

Conditions
ConditionsYield
In acetonitrile for 18h; Inert atmosphere; Schlenk technique; Reflux;99%
1592-20-7

4-Vinylbenzyl chloride

trioctyl(4-vinylbenzyl)phosphonium chloride

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;99%
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 48h; Inert atmosphere;
624-76-0

Iodoethanol

(2-hydroxyethyl)tri-n-octylphosphonium iodide

Conditions
ConditionsYield
at 60℃; for 5h; Inert atmosphere;99%
78-50-2

cyanex-921

Conditions
ConditionsYield
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
3188-13-4

ethyl chloromethyl ether

1273586-10-9

tri-n-octylmethoxyethylphosphonium chloride

Conditions
ConditionsYield
at 50℃; for 72h; Inert atmosphere;97%
109-69-3

n-Butyl chloride

56254-98-9

C28H60P(1+)*Cl(1-)

Conditions
ConditionsYield
at 180℃; under 2250.23 Torr; for 0.5h; Microwave irradiation; Inert atmosphere; neat (no solvent);97%
543-59-9

1-Chloropentane

56155-23-8

C29H62P(1+)*Cl(1-)

Conditions
ConditionsYield
at 145℃; for 12h; Inert atmosphere; neat (no solvent);96%
111-85-3

1-Chlorooctane

37165-84-7

tetraoctylphosphonium chloride

Conditions
ConditionsYield
at 145℃; for 14h; Inert atmosphere; neat (no solvent);96%
at 145℃; for 24h; Autoclave;
540-54-5

1-Chloropropane

56155-22-7

C27H58P(1+)*Cl(1-)

Conditions
ConditionsYield
at 180℃; under 2250.23 Torr; for 0.5h; Microwave irradiation; Inert atmosphere; neat (no solvent);96%

4-vinylbenzyl sultone

4-(trioctylphosphonio)-1-(4-vinylphenyl)butane-2-sulfonate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 90℃; for 168h; Inert atmosphere;96%
629-06-1

1-Chloroheptane

1352944-92-3

C31H66P(1+)*Cl(1-)

Conditions
ConditionsYield
at 145℃; for 14h; Inert atmosphere; neat (no solvent);95%
2473-01-0

1-Chlorononane

1352944-93-4

C33H70P(1+)*Cl(1-)

Conditions
ConditionsYield
at 145℃; for 16h; Inert atmosphere; neat (no solvent);95%
1002-69-3

decyl chloride

1352944-94-5

C34H72P(1+)*Cl(1-)

Conditions
ConditionsYield
at 145℃; for 16h; Inert atmosphere; neat (no solvent);95%
96-24-2

3-monochloro-1,2-propanediol

688763-75-9

trioctyl(2,3-dihydroxypropyl)phosphonium chloride

Conditions
ConditionsYield
at 120℃; for 72h; Inert atmosphere; Neat (no solvent);95%
75-00-3

chloroethane

ethyl-trioctylphosphonium chloride

Conditions
ConditionsYield
at 140℃; under 3000.3 Torr; for 4.5h; Inert atmosphere; Autoclave; neat (no solvent);94%
544-10-5

1-Chlorohexane

56255-18-6

C30H64P(1+)*Cl(1-)

Conditions
ConditionsYield
at 145℃; for 12h; Inert atmosphere; neat (no solvent);94%
34331-40-3

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate

1353746-15-2

CH3O3S(1-)*C30H62O2P(1+)

Conditions
ConditionsYield
at 120℃; for 72h; Inert atmosphere; Neat (no solvent);93%
4101-68-2

1,10-dibromodecane

53782-85-7

1,10-di(trioctylphosphonium bromide)decane

Conditions
ConditionsYield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;93%
74-87-3

methylene chloride

35675-28-6

methyltrioctylphosphonium chloride

Conditions
ConditionsYield
at 140℃; under 3000.3 Torr; for 2.5h; Inert atmosphere; Autoclave; neat (no solvent);92%
at 100℃; for 12h; Autoclave;
112-52-7

1-chlorododecane

1352944-95-6

trioctyl(dodecyl)phosphonium chloride

Conditions
ConditionsYield
at 145℃; for 16h; Inert atmosphere; neat (no solvent);92%
30515-28-7

7-bromoheptanoic acid

C31H64O2P(1+)*Br(1-)

Conditions
ConditionsYield
In acetonitrile at 80℃; for 48h;92%
57483-09-7

(3-iodopropyl)triethoxysilane

trioctyl(3-(triethoxysilyl)propyl)phosphonium iodide

Conditions
ConditionsYield
In toluene at 130℃; Inert atmosphere;92%
23737-51-1

solketal tosylate

1353746-17-4

C7H7O3S(1-)*C30H62O2P(1+)

Conditions
ConditionsYield
at 120℃; for 48h; Inert atmosphere; Neat (no solvent);91%
629-03-8

1 ,6-dibromohexane

103554-07-0

1,6-di(trioctylphosphonium bromide)hexane

Conditions
ConditionsYield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;91%
90224-27-4

octylphosphinous dibromide

Conditions
ConditionsYield
With phosphorus tribromide at 200℃; for 5h;90%
Multi-step reaction with 2 steps
1: 3 g / PBr3 / 6 h / Heating; nitrogen atmosphere
2: 83 percent / PBr3 / 5 h / 255 - 260 °C
View Scheme
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

C30H55PF9(1+)*I(1-)

Conditions
ConditionsYield
at 20℃; for 48h;90%
Inert atmosphere; Heating;
1120-71-4

1,3-propanesultone

C27H57O3PS

Conditions
ConditionsYield
In toluene at 90℃; for 72h; Inert atmosphere;90%

Trioctylphosphine Specification

The Phosphine, trioctyl-, with its CAS registry number 4731-53-7, has the IUPAC name of trioctylphosphane. For being sensitive to air,  it has the product categories which are including Tertiary Phosphines; Mitsunobu Reaction; Phosphine Ligands; Phosphines (Mitsunobu Reaction); Synthetic Organic Chemistry; Catalysis and Inorganic Chemistry; Phosphine Ligands; Phosphorus Compounds.

The characteristics of this chemical are as below: (1)ACD/LogP: 11.98; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 11.98; (4)ACD/LogD (pH 7.4): 11.98; (5)#H bond acceptors: 0; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 21; (8)Polar Surface Area: 13.59; (9)Flash Point: 236 °C; (10)Enthalpy of Vaporization: 67.59 kJ/mol; (11)Boiling Point: 445 °C at 760 mmHg; (12)Vapour Pressure: 1.07E-07 mmHg at 25°C; (13)Exact Mass: 370.372838; (14)MonoIsotopic Mass: 370.372838; (15)Heavy Atom Count: 25; (16)Complexity: 188; (17)Covalently-Bonded Unit Count: 1.

Production method of this chemical: Dioctylmagnesium could react to produce Phosphine, trioctyl-. This reaction happens in the presence of the reagent of PCl3.

Use of this chemical: Phosphine, trioctyl- could react to produce dichloro-octyl-phosphine. This reaction could happen in the presence of the reagent of PCl3. And it needs the reaction time of 1 hour and the reaction temperature of 275 ℃.

When you are dealing with this chemical, you should be more cautious. For one thing, it is irritant which may cause inflammation to the skin or other mucous membranes, and it is irritating to eyes, respiratory system and skin. For another thing, it is corrosive which may destroy living tissue on contact, and it may causes burns.

Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).

In adddition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCCCCCCCP(CCCCCCCC)CCCCCCCC
(2)InChI: InChI=1S/C24H51P/c1-4-7-10-13-16-19-22-25(23-20-17-14-11-8-5-2)24-21-18-
15-12-9-6-3/h4-24H2,1-3H3
(3)InChIKey: RMZAYIKUYWXQPB-UHFFFAOYSA-N 

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