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% |
methanol
A
bromure de methoxyvinyltriphenylphosphonium
B
triphenylphosphine
Conditions | Yield |
---|---|
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature; | A 86% B 100% |
A
bromure de methoxyvinyltriphenylphosphonium
B
triphenylphosphine
Conditions | Yield |
---|---|
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature; | A 86% B 100% |
triphenylphosphinediiodogermylene
phenyllithium
A
iodobenzene
B
biphenyl
C
triphenylgermane
D
tetraphenylgermane
E
triphenylphosphine
Conditions | Yield |
---|---|
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:4 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.; | A 10% B 13% C 39% D 36% E 100% |
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:1 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.; | A 2.9% B 2.9% C 1.9% D 14% E 82% |
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:2 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.; | A 7.7% B 9.6% C 1.3% D 19% E 79% |
methanol
triphenylphosphine borane
A
Trimethyl borate
B
triphenylphosphine
Conditions | Yield |
---|---|
at 120℃; Inert atmosphere; Microwave irradiation; | A n/a B 99% |
Conditions | Yield |
---|---|
With cis-[NiCl2(PPh3)2]; potassium tert-butylate In 1,4-dioxane at 90℃; for 10h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With 15-crown-5 In tetrahydrofuran at 25℃; for 16h; Reagent/catalyst; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tributylphosphine | 98% |
With sodium | |
With bis(2-methylphenyl)disulfide; triethylamine In chloroform for 7h; Heating; |
2-[2-Oxo-1-(triphenyl-λ5-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one
A
2-acetyl-4-oxo-dihydroquinazoline
B
triphenylphosphine
Conditions | Yield |
---|---|
In toluene at 95℃; for 2h; | A 98% B n/a |
Conditions | Yield |
---|---|
With potassium acetate; 5percent Pd on charcoal In N,N-dimethyl-formamide at 190℃; for 0.05h; microwave irradiation; | 98% |
With caesium carbonate In toluene at 115℃; for 24h; Inert atmosphere; | 90% |
With potassium acetate In N,N-dimethyl acetamide at 130℃; for 3h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; | 86% |
With rongalite; potassium hydroxide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 65% |
chlorobenzene
potassium diphenylphosphine
triphenylphosphine
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 25 - 67℃; for 74.4h; | 98% |
Conditions | Yield |
---|---|
With phosphorus tribromide | 97.3% |
With anhydrous phosphorus trichloride In toluene |
cis-dichlorobis(triphenylphosphine)platinum(II)
cyclenphosphorane
cis-((H2cyclen)P)PtCl2PPh3}Cl
{(eta.2-cyclenphosphorane)PtClPPh3}
C
triphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran under N2, mixt. of phosphorane and Pt complex in THF was stirred for 12h, pptn.; volatiles removed in vac., residue washed (10 times hexane, 10 times THF (to dissolve the η2-complex), residue (cis complex) and washing (η2.-complex) pumped dry separately, each heated to 90°C under vac., elem. anal.; | A 96% B 97% C 97% |
Conditions | Yield |
---|---|
With 15-crown-5 In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; for 3h; Reagent/catalyst; Inert atmosphere; | 97% |
Diphenylphosphonigsaeure-trimethylsilylester
phenyllithium
triphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 25℃; for 2h; | 97% |
Conditions | Yield |
---|---|
96.6% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 1h; Product distribution; Further Variations:; Reaction partners; reaction times; | 96% |
With n In tetrahydrofuran at 60℃; for 3h; | 95% |
Stage #1: triphenylphosphine sulfide With oxalyl dichloride In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 20℃; for 0.5h; Inert atmosphere; | 88% |
2-methyl-2-(triphenylphosphonio)dithiopropionate betaine
dimethyl acetylenedicarboxylate
A
2-isopropylidene-4,5-dimethoxycarbonyl-1,3-dithiole
B
triphenylphosphine
Conditions | Yield |
---|---|
In acetonitrile for 24h; Ambient temperature; | A 96% B 67% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 2h; | 96% |
Conditions | Yield |
---|---|
In chloroform soln. of educt in CHCl3 heated to 60°C and stirred for 0.5 h under N2, cooled; concd. in vac., chromd. (SiO2, C6H6), 1st colorless fraction contained PPh3, red 2nd fraction collected, concd.; | A 96% B n/a |
Conditions | Yield |
---|---|
In methanol for 0.75h; Ambient temperature; | A 95% B 89% |
ethanol
triphenylphosphine borane
A
triethyl borate
B
triphenylphosphine
Conditions | Yield |
---|---|
Inert atmosphere; Reflux; | A n/a B 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol for 96h; Inert atmosphere; Molecular sieve; Reflux; | 95% |
With diisopropylamine In toluene at 30℃; Kinetics; Equilibrium constant; Reagent/catalyst; Solvent; |
triphenylphosphine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 4.5h; Inert atmosphere; Cooling with ice; | 95% |
3,3,4,4-tetramethyl-1,2-dioxetane
2,2-Dihydro-4,4,5,5-tetramethyl-2,2,2-triphenyl-1,3,2-dioxaphospholane
A
3,3-dimethyl-butan-2-one
B
triphenylphosphine
Conditions | Yield |
---|---|
In benzene-d6 at 23.9℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, Ea, ΔS(excit); | A 6% B 94% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride at 120℃; for 0.5h; Inert atmosphere; | 93% |
With nickel tetrafluoroborate; lithium chloride In acetonitrile electrolysis; var. supporting electrolytes, other aryl and alkyl halides; | 80% |
With pyridine; tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 20h; Heating; |
2-{[(Toluene-4-sulfonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-azo}-benzaldehyde
A
2-p.tosyl-4-oxo-dihydroquinazoline
B
triphenylphosphine
Conditions | Yield |
---|---|
In toluene at 70℃; for 5h; | A 93% B n/a |
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; potassium tert-butylate In 1,4-dioxane at 90℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); sodium carbonate In 1,4-dioxane at 160℃; for 48h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 93% |
1,3-propanesultone
triphenylphosphine
3-(triphenylphosphonio)propane-1-sulfonate
Conditions | Yield |
---|---|
In toluene for 12h; Reflux; | 100% |
In tetrahydrofuran at 25℃; | 95% |
In toluene for 24h; Reflux; | 43% |
Conditions | Yield |
---|---|
In xylene for 0.00833333h; Heating; microwave irradiation; | 100% |
In toluene for 12h; Reflux; | 100% |
at 100℃; for 0.0333333h; Irradiation; | 99% |
chloromethyl methyl ether
triphenylphosphine
(methoxymethyl)triphenylphosphonium chloride
Conditions | Yield |
---|---|
In dichloromethane Reflux; | 100% |
In toluene at 95℃; for 16h; | 97.3% |
In neat (no solvent) at 80℃; for 4h; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique; | 93% |
1-dodecylbromide
triphenylphosphine
dodecyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene Reflux; | 100% |
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h; | 96.1% |
In tetrahydrofuran for 12h; sealed tube, bath temperature 250 deg C; | 88% |
bromoacetic acid methyl ester
triphenylphosphine
(methyloxycarbonylmethyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 17h; | 100% |
In ethyl acetate | 97% |
In benzene at 20℃; for 4h; | 97% |
α-bromoacetophenone
triphenylphosphine
triphenylphenacylphosphonium bromide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 100% |
at 20℃; for 24h; | 100% |
In toluene for 4h; Reflux; | 99% |
p-methoxy-phenylazide
triphenylphosphine
4-methoxy-N-(triphenylphosphoran-ylidene)-aniline
Conditions | Yield |
---|---|
In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere; | 100% |
In diethyl ether at 20℃; for 2h; | 88% |
triphenylphosphine
1,3-dibromo-propane
3-bromopropyltriphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene at 110℃; for 16h; | 100% |
In toluene for 24h; Reflux; | 99% |
In toluene Inert atmosphere; Reflux; | 98% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 2h; Condensation; | 100% |
In diethyl ether for 2h; Heating; | 100% |
In diethyl ether at 20℃; for 2h; | 79% |
triphenylphosphine
hexadecanyl bromide
(1-hexadecyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene Reflux; | 100% |
In toluene at 90℃; for 48h; | 79% |
In acetonitrile for 36h; Heating; | 68% |
triphenylphosphine
diazodiphenylmethane
diphenyldiazomethane triphenylphosphazine
Conditions | Yield |
---|---|
In benzene at 30℃; for 0.00333333h; | 100% |
In acetonitrile at 30℃; Rate constant; | |
In acetonitrile at 30℃; Kinetics; Thermodynamic data; effect of 4,4'-disubstitution on the reactivity; |
Conditions | Yield |
---|---|
for 0.00833333h; Heating; microwave irradiation; | 100% |
In toluene at 0℃; for 4h; Reflux; | 100% |
In dichloromethane at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In benzene at 30℃; for 0.00333333h; | 100% |
With benzene | |
In acetonitrile | |
In acetonitrile Yield given; |
Conditions | Yield |
---|---|
With selenium In toluene for 6h; Heating; | 100% |
With 4-phenyl-1,2,3-selenadiazole In benzene for 1h; Heating; | 100% |
With selenium In chloroform-d1 at 20℃; | 100% |
Conditions | Yield |
---|---|
With iodine In diethyl ether at 20℃; for 1h; | 100% |
With iodine In diethyl ether; toluene | 96% |
With iodine | |
With 1,2-Diiodoethane In acetonitrile at 60℃; for 0.5h; | |
With iodine In dichloromethane at 0℃; for 2h; |
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% |
p-Methoxybenzyl bromide
triphenylphosphine
((4-methoxyphenyl)methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In benzene for 24h; Ambient temperature; | 100% |
In toluene at 110℃; | 99% |
In toluene for 10h; Inert atmosphere; Reflux; | 98% |
Conditions | Yield |
---|---|
In toluene at 110℃; Inert atmosphere; | 100% |
In toluene Inert atmosphere; Reflux; | 98% |
In toluene for 18h; Inert atmosphere; Reflux; | 98% |
4-Methylbenzyl chloride
triphenylphosphine
(4-methylbenzyl)triphenylphosphonium chloride
Conditions | Yield |
---|---|
In acetonitrile for 4.5h; Reflux; | 100% |
In acetonitrile for 4.5h; Reflux; | 100% |
In xylene for 18h; Heating; | 86% |
1-bromomethyl-4-bromobenzene
triphenylphosphine
4-bromobenzyl triphenylphosphonium bromide
Conditions | Yield |
---|---|
In chloroform for 4h; Heating / reflux; | 100% |
In acetonitrile for 4.5h; Reflux; | 100% |
In acetone at 20℃; for 12h; | 99% |
1-bromo-4-butene
triphenylphosphine
but-3-en-1-yltriphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene for 24h; Inert atmosphere; Reflux; | 100% |
In N,N-dimethyl-formamide for 3h; Heating; | 84% |
In acetonitrile at 23℃; for 23h; Reflux; Inert atmosphere; | 81% |
triphenylphosphine
prenyl bromide
(3-methylbut-2-enyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene at 110℃; Inert atmosphere; | 100% |
In benzene at 20℃; for 20h; | 96% |
In toluene Ambient temperature; | 93% |
[14C]methyl iodide
triphenylphosphine
-methyltriphenylphosphonium iodide
Conditions | Yield |
---|---|
In benzene at 22℃; for 37h; | 100% |
In diethyl ether Methylation; | 95% |
In benzene for 24h; | 90% |
(E)-1-bromo-2-hexene
triphenylphosphine
<(E)-hex-2-enyl>triphenylphosphonium bromide
Conditions | Yield |
---|---|
In benzene for 5h; Heating; | 100% |
Conditions | Yield |
---|---|
In toluene for 8h; Reflux; | 100% |
In acetonitrile for 16h; Heating; | 95.6% |
In toluene for 120h; Heating; | 92% |
iodomethane-d3
triphenylphosphine
(methyl-d3)triphenylphosphonium iodide
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; Reflux; | 100% |
In tetrahydrofuran for 1h; Schlenk technique; Reflux; | 99% |
In tetrahydrofuran for 1h; Schlenk technique; Inert atmosphere; Reflux; | 99% |
Conditions | Yield |
---|---|
In chlorobenzene for 48h; Heating; | 100% |
In toluene Reflux; | 100% |
In o-xylene Heating; | 98.7% |
1-Bromotetradecane
triphenylphosphine
(n-tetradecyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene Reflux; | 100% |
at 140℃; for 7h; | 92% |
In benzene for 48h; Substitution; Heating; | 92% |
6-bromohexanoic acid
triphenylphosphine
(5-carboxypentyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In acetonitrile for 16h; Heating; | 100% |
at 100℃; for 4h; | 100% |
In acetonitrile for 24h; Heating; | 99% |
1. Introduction of Triphenylphosphine
Triphenylphosphine, its cas register number is 603-35-0. It also can be called Phosphine, triphenyl-; Trifenylfosfin; Trifenylfosfin [Czech]; Triphenyl phosphine.The IUPAC Nameis triphenylphosphane. It exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
2. Properties of Triphenylphosphine
Molecular Weight: 262.285461 [g/mol]
Molecular Formula: C18H15P
XLogP3-AA: 4.6
Melting Point: 79-81 °C(lit.)
Flash Point: 181.7 °C
Enthalpy of Vaporization: 58.18 kJ/mol
Boiling Point: 360 °C at 760 mmHg
Vapour Pressure: 4.74E-05 mmHg at 25°C
Density: 1.132 g/cm3
Storage temp.: Store at RT.
Water Solubility: Insoluble
Stability: Stable. Incompatible with oxidizing agents, acids.
3. Toxicity of Triphenylphosphine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LDLo | oral | 9gm/kg (9000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014, |
dog | LD50 | oral | > 500mg/kg (500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | National Technical Information Service. Vol. OTS0570648, |
mouse | LD50 | oral | 1gm/kg (1000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014, |
mouse | LD50 | subcutaneous | 3gm/kg (3000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014, |
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974. | |
rat | LC50 | inhalation | 1135ppm/4H (1135ppm) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Annual Meeting of American Industrial Hygiene Association. Vol. -, Pg. -, 1969. |
rat | LD50 | intramuscular | 1500mg/kg (1500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014, |
rat | LD50 | oral | 700mg/kg (700mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0384-0014, |
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