Conditions | Yield |
---|---|
With CuO2H In acetonitrile at 70℃; for 6h; | 100% |
With CuO2H In acetonitrile at 70℃; for 6h; | 100% |
With periodate form of Amberlyst A26 In chloroform at 25℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With pyridine; trifluoroacetic anhydride for 2h; | 100% |
With hexyl sulfide; oxygen In methanol; chloroform for 0.5h; Irradiation; | 100% |
With hexyl sulfide In methanol; chloroform for 1h; Product distribution; Irradiation; other reagents; | 100% |
9-fluorenone triphenylphosphazine
A
9-fluorenone
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With oxygen; methylene blue In dichloromethane at -78℃; for 0.0833333h; Irradiation; other reagent; | A 100% B n/a |
With oxygen; methylene blue In dichloromethane Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
With bromonitromethane In benzene | A 100% B 88% |
With bromonitromethane In benzene for 12h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 20h; Mechanism; other thiophosphoramides are also investigated; | 100% |
With 3,3-dimethyldioxirane In dichloromethane; acetone for 0.0833333h; Ambient temperature; | 100% |
With pyridine; trifluoroacetic anhydride for 3h; | 100% |
[bis(acetoxy)iodo]benzene
triphenylphosphine
benzylamine
A
N-(phenylmethyl)acetamide
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
Stage #1: [bis(acetoxy)iodo]benzene; triphenylphosphine In chloroform for 1h; Heating; Stage #2: benzylamine In chloroform for 0.166667h; | A 94% B 100% |
3,3-diphenyl-1,2-indanedione
methyl (triphenylphosphoranylidene)acetate
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene at 20℃; for 5h; Wittig reaction; | A 70% B 11% C 100% |
3,3-diphenyl-1,2-indanedione
ethyl (triphenylphosphoranylidene)acetate
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene at 20℃; for 5h; Wittig reaction; | A 65% B 14% C 100% |
3,3-diphenyl-1,2-indanedione
cyanomethylene triphenylphosphorane
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene at 20℃; for 7h; Wittig reaction; | A 63% B 17% C 100% |
(Z)-3-(4-bromophenyl)-3-iodoprop-2-en-1-ol
A
1-bromo-4-((Z)-3-bromo-1-iodopropenyl)benzene
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; | A 100% B n/a |
Conditions | Yield |
---|---|
In perchloric acid; acetonitrile Kinetics; room temp.; | A n/a B 100% |
Conditions | Yield |
---|---|
In [D3]acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; | A n/a B 100% |
Conditions | Yield |
---|---|
In [D3]acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; | A n/a B 100% |
phenylsulfenyl methyl thiocarbonate
A
thiophenol
B
triphenylphosphine sulfide
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With triphenylphosphine In benzene Mechanism; Ambient temperature; reaction of var. sulfenyl thiocarbonates with triphenylphosphine; | A 99% B 1% C 99% |
phenyl isocyanate
{[2-(4-Methylphenyl)-1-phenylvinyl]imino}triphenylphosphoran
A
Phenyl-((E)-1-phenyl-2-p-tolyl-vinyl)-carbodiimide
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene for 2h; Ambient temperature; | A 90% B 99% |
N-(1,2-Diphenylvinyl)iminotriphenylphosphoran
p-Tolylisocyanate
A
((E)-1,2-Diphenyl-vinyl)-p-tolyl-carbodiimide
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene for 2h; Ambient temperature; | A 97% B 99% |
1,1,3,3-tetramethyl-2-indanone triphenyl-phosphoranylidenehydrazone
A
2,2,5,5,-tetramethyl-3,4-benzo-3-penten-5-olide
B
1,1,3,3-tetramethylindane-2-one
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With oxygen In dichloromethane at 15℃; for 16h; Irradiation; | A 9% B 68% C 99% |
With oxygen; methylene blue In dichloromethane at 15℃; for 16h; Irradiation; | A 9% B 68% C 99% |
With oxygen; methylene blue In dichloromethane at 15℃; for 16h; Product distribution; Mechanism; Irradiation; various sensitizers; |
trans-tetrachlorobis(pyridine)platinum(II)
methyl (triphenylphosphoranylidene)acetate
trans-dichlorobis(pyridine)platinum(II)
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
trans-tetrachlorobis(dimethyl sulfide) platinum(IV)
methyl (triphenylphosphoranylidene)acetate
trans-dichlorobis(dimethylsulfide)platinum(II)
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
trans-(PtCl4(py)(SMe2))
methyl (triphenylphosphoranylidene)acetate
trans-dichloro(dimethyl sulfide-κS)(pyridine-κ-N)platinum(II)
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
trans-(PtCl4(HON=CMe2)2)
methyl (triphenylphosphoranylidene)acetate
(SP-4-1)-bis(acetone oxime-κN)dichloridoplatinum(II)
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
methyl (triphenylphosphoranylidene)acetate
trans-(PtCl2(Me2SO)(NHEt2))
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
(PtCl4(NC(CH3)ON(CH3)CHC6H5)2)
methyl (triphenylphosphoranylidene)acetate
A
(PtCl2(NC(CH3)ON(CH3)CHC6H5)2)
B
(2-methoxy-2-oxoethyl)triphenylphosphonium chloride
C
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane Ph3P=CHCO2Me was added to soln. Pt(IV) complex in CH2Cl2, react. mixt. was kept at room temp. for 3 h; solvent was evapd., residue was chromed. on silica using CH2Cl2/Et2O (9:1) as eluent; | A 99% B n/a C n/a |
2-methoxy-6-phenylpyrimidin-4-ol
17-hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4.6*]-octadec-7-ene-4-carboxylic acid ethyl ester
triphenylphosphine
A
14-(4-methoxy-benzyl)-18-(2-methoxy-6-phenyl-pyrimidin-4-yloxy)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; | A 99% B n/a |
4-Phenylbenzaldehyde
methyl (triphenylphosphoranylidene)acetate
A
methyl (E)-3-([1′,1′′-biphenyl]-4′-yl)acrylate
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Wittig reaction; Inert atmosphere; | A 99% B n/a |
4-methoxy-o-phenyl phenyl(phenyl)phosphinate
phenylmagnesium bromide
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 99% |
pyridine-3,5-bis-carbaldehyde
(3-carboxypropyl)(triphenyl)phosphonium bromide
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 50℃; for 28h; | A 0.278 g B 98% |
1,1,1-trifluoroacetophenone
benzyltriphenylphosphonium bromide
A
1,2-diphenyl-3,3,3-trifluoroprop-1-ene
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With water; potassium carbonate In 1,4-dioxane at 95℃; for 3h; | A 98% B n/a |
n-butyl(triphenyl)phosphonium bromide
benzaldehyde
A
(Z)-pent-1-en-1-ylbenzene
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
With water; potassium carbonate In 1,4-dioxane Product distribution; Mechanism; further aldehydes and ketones; other solvents; other alkaline carbonates as reagens; stereoselectivity examined; | A 98% B n/a |
Cyclohexyl isocyanate
{[2-(4-Methylphenyl)-1-phenylvinyl]imino}triphenylphosphoran
A
Cyclohexyl-((E)-1-phenyl-2-p-tolyl-vinyl)-carbodiimide
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In benzene Ambient temperature; | A 94% B 98% |
Conditions | Yield |
---|---|
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 5h; | 100% |
With aluminium hydride*tetrahydrofuran | 100% |
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In methyl cyclohexane at 80℃; for 14h; | 100% |
Triphenylphosphine oxide
methyl trifluoromethanesulfonate
methoxytriphenylphosphonium trifluoromethanesulfonate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 100% |
In benzene Heating; | 90% |
In acetonitrile | 89% |
In acetonitrile at 20℃; for 1h; Inert atmosphere; |
benzene-1,2-diol
Triphenylphosphine oxide
triphenyl(1,2-phenylenedioxy)phosphorane
Conditions | Yield |
---|---|
at 70 - 80℃; for 2h; | 100% |
Conditions | Yield |
---|---|
at 100 - 110℃; for 2h; | 100% |
1-bromo-3,4-dihydroxybenzene
Triphenylphosphine oxide
Conditions | Yield |
---|---|
at 70 - 80℃; for 2h; | 100% |
3-bromo-5-tert-butyl-1,2-dihydroxybenzene
Triphenylphosphine oxide
Conditions | Yield |
---|---|
at 70 - 80℃; for 2h; | 100% |
Conditions | Yield |
---|---|
at 70 - 80℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With oxalyl dichloride In acetonitrile at 20℃; Inert atmosphere; | 100% |
With bis(trichloromethyl) carbonate In chloroform at 20℃; for 1h; | |
With oxalyl dichloride; tetrabutylammonium trifluoromethylsulfonate In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; | |
With oxalyl dichloride In acetonitrile Inert atmosphere; | |
With oxalyl dichloride In acetonitrile at 0 - 5℃; |
thiourea
Triphenylphosphine oxide
Conditions | Yield |
---|---|
at 95 - 100℃; for 4h; | 100% |
Conditions | Yield |
---|---|
at 95 - 100℃; for 4h; | 100% |
uranium(IV) chloride
Triphenylphosphine oxide
[UCl4(triphenylphosphine oxide)2]
Conditions | Yield |
---|---|
In tetrahydrofuran Glovebox; | 100% |
In tetrahydrofuran inert atmosphere; stirring UCl4 for 24 h, Ph3PO addn. (pptn.); collection (filtration), washing (PhMe, hexane); | 94% |
In tetrahydrofuran for 0.166667h; |
Conditions | Yield |
---|---|
In tetrahydrofuran 3 equiv. Ph3PO; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 100% |
In toluene at 0 - 23℃; for 1h; Inert atmosphere; Schlenk technique; | 97% |
Triphenylphosphine oxide
B
CF3O3S(1-)*C23H22N2P(1+)
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 20h; Inert atmosphere; | A 100% B 100% |
[ThCl4(1,2-dimethoxyethane)2]
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 6h; | 100% |
Conditions | Yield |
---|---|
In toluene for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; | 100% |
IUPAC Name: Diphenylphosphorylbenzene
Synonyms of Triphenyl Phosphine Oxide (CAS NO.791-28-6): 3-Acetylpropionic acid ; 4-Ketovaleric acid ; 4-Oxopentanoic acid ; Acetopropionic acid ; Levulinic acid ; Propionic acid, 3-acetyl- ; gamma-Ketovaleric acid
CAS NO: 791-28-6
Molecular Formula: C18H15OP
Molecular Weight: 791-28-6
Molecular Structure:
EINECS: 212-338-8
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 26.88 Å2
Index of Refraction: 1.619
Molar Refractivity: 82.91 cm3
Molar Volume: 236.2 cm3
Surface Tension: 48.2 dyne/cm
Density: 1.17 g/cm3
Flash Point: 233.8 °C
Enthalpy of Vaporization: 69.63 kJ/mol
Boiling Point: 462.9 °C at 760 mmHg
Vapour Pressure: 2.62E-08 mmHg at 25°C
Melting point: 154-158 °C
Storage temp: Store at RT
Solubility methanol: 25 mg/mL, clear
Water solubility: slightly soluble
Appearance: White solid
Product Categories of Triphenyl Phosphine Oxide (CAS NO.791-28-6): Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
Triphenyl Phosphine Oxide (CAS NO.791-28-6) is used for intermediates in organic synthesis and pharmaceutical, and it is also used for catalysts, extraction agents. Besides, it is still used for fluorescent anti-counterfeit powder.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 450mg/kg (450mg/kg) | National Technical Information Service. Vol. AD607-952, | |
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979. | |
rat | LD50 | oral | 1850mg/kg (1850mg/kg) | Food and Cosmetics Toxicology. Vol. 17, Pg. 847, 1979. |
Safety Information about Triphenyl Phosphine Oxide (CAS NO.791-28-6):
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38-52/53
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-61-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
WGK Germany: 2
RTECS: SZ1676000
HS Code: 29310095
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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