Conditions | Yield |
---|---|
With Hexamethylphosphorous triamide In toluene at 130℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | 100% |
With phosphorus trichloride at 35 - 160℃; under 7.50075 Torr; for 6h; Temperature; Flow reactor; Inert atmosphere; | 94% |
With 1H-imidazole; carbon disulfide; Hexamethylphosphorous triamide In benzene at 20 - 25℃; for 24h; | 86% |
triphenyl phosphite
Conditions | Yield |
---|---|
With tert-butyl alcohol; 4 A molecular sieve In tetrahydrofuran at 25℃; for 72h; | 100% |
With piperazinomethyl polystyrene resin In toluene at 60℃; for 1.5h; |
phenylphosphonic acid bis(N,N-diethylamide)
aniline
A
triphenyl phosphite
B
N,N',N''-triphenylphosphorous triamide
C
phenyl N,N'-diphenylphosphorodiamidite
D
diphenyl phenylphosphoramidite
E
diethylamine
Conditions | Yield |
---|---|
for 17h; Product distribution; Heating; | A n/a B n/a C n/a D n/a E 94.5% |
phenylphosphonic acid bis(N,N-diethylamide)
4-bromo-aniline
A
triphenyl phosphite
B
diethylamine
Conditions | Yield |
---|---|
for 22h; Product distribution; Heating; | A n/a B 91.4% C n/a D n/a E n/a |
methanol
phosphorus trichloride
A
triphenyl phosphite
B
dimethyl phenylphosphonite
C
diphenyl methylphosphonate
Conditions | Yield |
---|---|
Stage #1: phosphorus trichloride; phenol at 65 - 250℃; for 3 - 4h; Stage #2: methanol; methyl iodide at 210 - 250℃; for 1h; Product distribution / selectivity; | A 4.5% B 4.8% C 85.5% |
Conditions | Yield |
---|---|
With tetrachloromethane; phosphorous; 15-crown-5 at 50 - 70℃; for 3h; | 85% |
2-diethylamino-5-methyl-1,3,2-oxathiaphospholene
phenol
triphenyl phosphite
Conditions | Yield |
---|---|
at 20℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With pyridine In acetonitrile at 50℃; electrosynthesis; | A 78% B 20% |
chlorotriphenoxy(trichloroacetyl)phosphorane
A
triphenyl phosphite
B
Diphenyl phosphorochloridite
C
Trichloroacetyl chloride
Conditions | Yield |
---|---|
at 50℃; under 10 Torr; Mechanism; | A n/a B n/a C 63.6% |
trichloromethylphosphonous dichloride
phenol
A
triphenyl phosphite
B
chloroform
C
phosphoric acid triphenyl ester
Conditions | Yield |
---|---|
A 55.6% B 34% C 6.7% |
A
triphenyl phosphite
B
[Pd[P(OPh)3]3]
C
diphenyl phenylphosphonate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 160℃; for 4h; Inert atmosphere; | A n/a B n/a C 37% D 15% |
phenol
2,4-dichloro-1,3-diphenyl-cyclodiphosphazane
A
triphenyl phosphite
B
aniline hydrochloride
Conditions | Yield |
---|---|
With phenol Equilibrium constant; |
Diphenyl phosphorochloridite
A
triphenyl phosphite
B
phenyl phosphorodichloridite
Conditions | Yield |
---|---|
at 140℃; Equilibrium constant; |
diphenyl bromophosphite
A
triphenyl phosphite
B
phenyl dibromophosphite
Conditions | Yield |
---|---|
at 140℃; Equilibrium constant; |
diphenyl phenylphosphonite
phenyl-phosphonochloridous acid phenyl ester
A
triphenyl phosphite
B
Dichlorophenylphosphine
Conditions | Yield |
---|---|
at 140℃; Equilibrium constant; |
dineopentyl phenyl phosphite
A
triphenyl phosphite
B
diphenyl methylphosphonate
C
Methyl-phosphonic acid 2,2-dimethyl-propyl ester phenyl ester
D
neopentyl diphenyl phosphite
Conditions | Yield |
---|---|
With methyl iodide In neat (no solvent) at 33℃; for 1080h; Title compound not separated from byproducts; | A n/a B 28 % Spectr. C 11 % Spectr. D 27 % Spectr. |
dineopentyl phenyl phosphite
methyl iodide
A
triphenyl phosphite
B
diphenyl methylphosphonate
C
Methyl-phosphonic acid 2,2-dimethyl-propyl ester phenyl ester
Conditions | Yield |
---|---|
In neat (no solvent) at 33℃; for 1080h; Title compound not separated from byproducts; | A n/a B 28 % Spectr. C 11 % Spectr. |
dineopentyl phenyl phosphite
methyl iodide
A
triphenyl phosphite
B
diphenyl methylphosphonate
C
Methyl-phosphonic acid 2,2-dimethyl-propyl ester phenyl ester
D
neopentyl diphenyl phosphite
Conditions | Yield |
---|---|
In neat (no solvent) at 33℃; for 1080h; Title compound not separated from byproducts; | A n/a B 28 % Spectr. C 11 % Spectr. D 27 % Spectr. |
phenol
A
triphenyl phosphite
B
Phosphorous acid 2-ethyl-phenyl ester diphenyl ester
C
Phosphorous acid 2,6-diethyl-phenyl ester diphenyl ester
D
Phosphorous acid 2,6-diethyl-phenyl ester 2-ethyl-phenyl ester phenyl ester
Conditions | Yield |
---|---|
With o-Hydroxyethylbenzene; 2,6-diethylphenol; triethylamine; phosphorus trichloride In toluene for 1h; Heating; Further byproducts given; | A 9.2 % Chromat. B 21.5 % Chromat. C 26.2 % Chromat. D 21.3 % Chromat. |
ethanol
diphenyl hydrogen phosphite
A
triphenyl phosphite
B
phosphorous acid ethyl ester-diphenyl ester
Conditions | Yield |
---|---|
With pyridine; pivaloyl chloride Multistep reaction; |
diphenyl hydrogen phosphite
A
triphenyl phosphite
B
phenyl hydrogen phosphonate
Conditions | Yield |
---|---|
With pyridine Mechanism; also thio derivative, var. reagents and solvents; | |
With trityl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 0.166667h; Disproportionation; |
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With pyridine |
phenyl H-phosphonate ammonium salt
chlorophosphoric acid diphenyl ester
A
triphenyl phosphite
B
tetraphenyl pyrophosphite
Conditions | Yield |
---|---|
With pyridine |
triphenyl phosphite
Conditions | Yield |
---|---|
With phosphorus trichloride; benzene |
tetraphenoxysilane
phosphorus trichloride
benzene
triphenyl phosphite
Conditions | Yield |
---|---|
beim Erwaermen; |
Conditions | Yield |
---|---|
With bis(2,4,6-triisopropylphenyl) telluroxide In acetonitrile at 20℃; for 0.5h; | 100% |
With 1-methyl-3-(4-((2,4,6-triisopropylphenyl)tellanyl)benzyl)-1H-imidazol-3-ium hexafluorophosphate; Rose Bengal lactone at 15℃; for 2.5h; Reagent/catalyst; Irradiation; Ionic liquid; | 99% |
With iodosylbenzene; Montmorillonite K10 In acetonitrile at 20℃; for 2h; | 93% |
triphenyl phosphite
ethene
N-ethyl-N-phenylamine
A
2-(1-butenyl)aniline
B
N-ethyl-p-tolylamine
Conditions | Yield |
---|---|
With aniline; Fe(CO)5 | A n/a B 100% |
triphenyl phosphite
Ru2(CO)5(COC2H5)2(P(OC6H5)3)
Conditions | Yield |
---|---|
In hexane the reactants are mixed at room temp. under N2, react. time is ca 1 min; concg., chromy. on silica gel (CH2Cl2/petroleum ether); | 100% |
triphenyl phosphite
tetraethyl ammonium pentacarbonyl (triphenyl phosphine) vanadat
tetraethylammonium pentacarbonyl(triphenylphosphite)vanadate
Conditions | Yield |
---|---|
In tetrahydrofuran Kinetics; under N2 or Ar, ca. 20-fold excess of P(OPh)3, 68°C; detected by IR; | 100% |
triphenyl phosphite
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
cis-{molybdenum(0)(carbonyl)4(P(O-phenyl)3)2}
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In tetrahydrofuran under argon; reaction in a calorimeter; | A 100% B n/a |
Conditions | Yield |
---|---|
In benzene-d6 complex dissolved in C6D6 under N2, 4 equiv. of P(OPh)3 added at 25°C;; | 100% |
triphenyl phosphite
tetrakis(triphenylphosphine) palladium(0)
tetrakis(triphenyl phosphite)palladium(0)
Conditions | Yield |
---|---|
In benzene excess of P(OPh)3 was added to a soln. of the Pd complex in benzene; | 100% |
triphenyl phosphite
(C2H5)4N(1+)*V(CO)5P((CH2)3CH3)3(1-)
tetraethylammonium pentacarbonyl(triphenylphosphite)vanadate
Conditions | Yield |
---|---|
In tetrahydrofuran Kinetics; under N2 or Ar, ca. 20-fold excess of P(OPh)3, 68°C; detected by IR; | 100% |
triphenyl phosphite
Na(1+)*V(CO)5P(C4H9)3(1-)=NaV(CO)5P(C4H9)3
Na(1+)*V(CO)5P(OC6H5)3(1-)*3C4H8O=NaV(CO)5P(OC6H5)3*3C4H8O
Conditions | Yield |
---|---|
In tetrahydrofuran Kinetics; under N2 or Ar, ca. 20-fold excess of P(OPh)3, 68°C; detected by IR; | 100% |
triphenyl phosphite
Na(1+)*V(CO)5P(C6H5)3(1-)*3C4H8O=NaV(CO)5P(C6H5)3*3C4H8O
Na(1+)*V(CO)5P(OC6H5)3(1-)*3C4H8O=NaV(CO)5P(OC6H5)3*3C4H8O
Conditions | Yield |
---|---|
With tetrahydrofuran In tetrahydrofuran Kinetics; under N2 or Ar, ca. 20-fold excess of P(OPh)3, 68°C; detected by IR; | 100% |
In tetrahydrofuran under N2 or Ar, addn. of 20-fold excess P(OPh)3 to THF soln. of complex, stirred for about 1.5 h, addn. of hexane; washed with hexane, recrystd. from THF/hexane; |
triphenyl phosphite
[Ru(η5,η1-C5H2Me2CO2(CH2)2PPh2)(CH3CN)2][PF6]
[(CH3(C5H2)CH3)Ru(CH3CN)P(OC6H5)3COOCH2CH2P(C6H5)2](1+)*PF6(1-)=[(CH3(C5H2)CH3)Ru(CH3CN)P(OC6H5)3COOCH2CH2P(C6H5)2]PF6
Conditions | Yield |
---|---|
In acetone 1:1.1 mixt. stirred at room temp. for 3 h; NMR, XRD; | 100% |
triphenyl phosphite
[Ru(η5,η1-C5H2(Me)(t-Bu)CO2(CH2)2PPh2)(CH3CN)2][PF6]
Conditions | Yield |
---|---|
In acetone 1:1.1 mixt. stirred at room temp. for 3 h; NMR; | 100% |
triphenyl phosphite
[Ru(η5,η1-C5H2(Me)(Ph)CO2(CH2)2PPh2)(CH3CN)2][PF6]
[(CH3(C5H2)C6H5)Ru(CH3CN)P(OC6H5)3COOCH2CH2P(C6H5)2](1+)*PF6(1-)=[(CH3(C5H2)C6H5)Ru(CH3CN)P(OC6H5)3COOCH2CH2P(C6H5)2]PF6
Conditions | Yield |
---|---|
In acetone 1:1.1 mixt. stirred at room temp. for 3 h; NMR; | 100% |
triphenyl phosphite
carbonylchlorohydridotris(triphenylphosphine)ruthenium(II)
Conditions | Yield |
---|---|
In benzene N2-atmosphere; standing overnight; evapn. (reduced pressure, room temp.), washing (hexane), recrystn. (CH2Cl2/MeOH); elem. anal.; | 100% |
[2-benzyl-1-(4-methoxy-phenyl)-allyloxy]-triethyl-silane
triphenyl phosphite
C23H22O2
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 0 - 20℃; for 11h; stereoselective reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: triphenyl phosphite With bis(p-dimethylaminophenyl)methanone at 120℃; for 1h; Inert atmosphere; Stage #2: non-1-ene at 130 - 140℃; under 750.075 Torr; Reagent/catalyst; Temperature; Pressure; UV-irradiation; Autoclave; | 99.56% |
triphenyl phosphite
(P(C6H5)3)3Rh(CO)2(1+)*(HC(SO2CF3)2)(1-)=P3(C6H5)9RhC2O2HC(SO2CF3)2
(P((C6H5)O)3)4Rh(1+)*(HC(SO2CF3)2)(1-)=(P(C6H5)3O3)4RhHC(SO2CF3)2
Conditions | Yield |
---|---|
In not given byproducts: CO; | 99% |
Conditions | Yield |
---|---|
In dichloromethane stirring (10 min); evapn. (vac.), crystn. (CH2Cl2/pentane); elem. anal.; | 99% |
triphenyl phosphite
Os3(μ-H)2(CO)10
(μ-H)HOs3(CO)10(P(OPh)3)
Conditions | Yield |
---|---|
In n-heptane; dichloromethane in CH2Cl2/heptane=1:10 v/v, equimolar amts., room temp. (UV-control); vol. reduction (Ar-stream), crystn. (-15°C); | 99% |
triphenyl phosphite
Conditions | Yield |
---|---|
In toluene equimol.; | 99% |
triphenyl phosphite
cis-[Pt(p-CH3C6H4)2(S(CH3)2)2]
cis-[Pt(p-MeC6H4)2(P(OPh)3)2]
Conditions | Yield |
---|---|
In benzene byproducts: S(CH3)2; addn. of a soln. of 2 equivs. phosphite in benzene to a soln. of platinum complex in benzene, stirring at room temp. for 1 h; evapn. in vac.; elem. anal.; | A 0% B 99% |
triphenyl phosphite
cis-[Me2Pt{P(OPh)3}(SMe2)]
Conditions | Yield |
---|---|
In benzene byproducts: S(CH3)2; addn. of a soln. of 2 equivs. phosphite in benzene to a soln. of platinum complex in benzene, stirring at room temp. for 1 h; evapn. in vac.; elem. anal.; | 99% |
triphenyl phosphite
cis-[Me2Pt{P(OPh)3}2]
Conditions | Yield |
---|---|
In benzene byproducts: S(CH3)2; addn. of a soln. of 4 equivs. phosphite in benzene to a soln. of platinum complex in benzene, stirring at room temp. for 1 h; evapn. in vac.; elem. anal.; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-toluidine With tert.-butylnitrite; toluene-4-sulfonic acid In acetonitrile at 0℃; for 0.25h; Sandmeyer Reaction; Stage #2: triphenyl phosphite In acetonitrile at 0.25℃; for 0.166667h; Sandmeyer Reaction; | 99% |
With tert.-butylnitrite; salicylic acid In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 50% |
Conditions | Yield |
---|---|
Stage #1: 1-amino-4-nitronaphthalene With tert.-butylnitrite; toluene-4-sulfonic acid In acetonitrile at 0℃; for 0.25h; Sandmeyer Reaction; Stage #2: triphenyl phosphite In acetonitrile at 0.25℃; for 8h; | 99% |
Conditions | Yield |
---|---|
In benzene-d6 for 0.5h; | 99% |
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 16h; Oleksyszyn Synthesis; | 99% |
Conditions | Yield |
---|---|
Stage #1: Cyclohepta-1,3,5-triene With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Michaelis-Arbuzov Synthesis; Inert atmosphere; Stage #2: triphenyl phosphite | 99% |
Molecular Structure of Triphenyl phosphite (CAS NO.101-02-0):
IUPAC Name: triphenyl phosphite
Empirical Formula: C18H15O3P
Molecular Weight: 310.2837
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 41.28 Å2
Flash Point: 218.3 °C
Enthalpy of Vaporization: 58.18 kJ/mol
Boiling Point: 360 °C at 760 mmHg
Denny: 1.184 g/mL at 25 °C(lit.)
Vapour Pressure: 4.74E-05 mmHg at 25°C
Water solubility: insoluble
Melting point: 22-24 ºC
EINECS: 202-908-4
Sensitive: Air & Moisture Sensitive
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Product Categories: Catalysis and Inorganic Chemistry; Phosphite Ligands; Phosphorus Compounds
InChI
InChI=1/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H
Smiles
P(Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1
Chemical intermediate, stabilizer systems for resins, metal scavenger, diluent for epoxy resins.
Triphenyl phosphite is prepared from phosphorus trichloride and phenol in the presence of a base:
PCl3 + 3 HOC6H5 → P(OC6H5)3 + 3HCl
Trimethyl phosphine is prepared from triphenylphosphite:
3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intraperitoneal | 100mg/kg (100mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR | National Technical Information Service. Vol. OTS0570901, |
cat | LDLo | subcutaneous | 300mg/kg (300mg/kg) | BEHAVIORAL: ATAXIA | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 78, 1933. |
chicken | LDLo | intravenous | 50mg/kg (50mg/kg) | AUTONOMIC NERVOUS SYSTEM: GAGLION BLOCK | Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 44, Pg. 118, 1989. |
chicken | LDLo | oral | 250mg/kg (250mg/kg) | BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0532280, |
chicken | LDLo | subcutaneous | 375mg/kg (375mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0532280, |
mammal (species unspecified) | LD50 | intraperitoneal | 250mg/kg (250mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES CARDIAC: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 5, Pg. 311, 1952. |
mouse | LD50 | intraperitoneal | 266mg/kg (266mg/kg) | Agricultural and Biological Chemistry. Vol. 31, Pg. 1288, 1967. | |
mouse | LD50 | oral | 1080mg/kg (1080mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(12), Pg. 53, 1987. | |
mouse | LD50 | unreported | 1360mg/kg (1360mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 55, 1977. |
rabbit | LDLo | skin | 5gm/kg (5000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | National Technical Information Service. Vol. OTS0532280, |
rat | LC | inhalation | > 6700mg/m3/1H (6700mg/m3) | National Technical Information Service. Vol. OTS0532280, | |
rat | LD50 | intraperitoneal | 250mg/kg (250mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1117, 1986. | |
rat | LD50 | oral | 444mg/kg (444mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(12), Pg. 13, 1981. | |
rat | LD50 | unreported | 1490mg/kg (1490mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 55, 1977. |
rat | LDLo | subcutaneous | 2gm/kg (2000mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: TREMOR BEHAVIORAL: MUSCLE WEAKNESS | Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 78, 1933. |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. An experimental eye and severe human skin irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, mist, dry chemical. When heated to decomposition, it emits toxic fumes of POx. See also Phenol.
Hazard Codes: XnN,Xi
Risk Statements: 36/38-50/53
R36/38:Irritating to eyes and skin.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 28-60-61-28A
S28:After contact with skin, wash immediately with plenty of soap-suds.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: TH1575000
HazardClass: 9
PackingGroup: III
HS Code: 29209085
Triphenyl phosphite , with CAS number of 101-02-0, can be called phosphorous acid, triphenyl ester ; Advance TPP ; Phenyl phosphite ; Sumilizer TPP-R ; Trifenoxyfosfin ; Tris(phenoxy)phosphine . It is a colourless to pale yellow liquid, be insoluble in water. Triphenyl phosphite (CAS NO.101-02-0) are susceptible to form highly toxic and flammable phosphine gas in the presence of strong reducing agents, such as hydrides. Partial oxidation may result in the release of toxic phosphorus oxides.
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