Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutylammomium bromide; zinc dibromide; silica gel; gold In decane at 80℃; under 60004.8 Torr; for 4h; | 100% |
With [aluminum((1R,2R)-N,N′-bis(3,5-di-tert-butyl-salicylidene)cyclohexane-1,2-diamine)2O]; tetrabutylammomium bromide at 60℃; under 3750.38 Torr; for 24h; Mechanism; Reagent/catalyst; Temperature; Pressure; Autoclave; | 100% |
With tetrabutylammomium bromide at 105℃; under 760.051 Torr; for 20h; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 2h; Reagent/catalyst; Solvent; | 99% |
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
With aluminum oxide; cesium fluoride at 129.85℃; for 0.416667h; | 98% |
aluminum oxide; cesium fluoride at 129.85℃; for 0.416667h; | 98% |
With MgLa mixed oxide at 125℃; for 2h; | 98% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide at 80℃; under 15001.5 Torr; for 10h; Reagent/catalyst; Time; Autoclave; | 98% |
With tert.-butylhydroperoxide; aniline In neat (no solvent) at 100℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Temperature; Pressure; | 97% |
With N-Bromosuccinimide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene at 60℃; under 12929 Torr; for 2 - 3h; Product distribution / selectivity; | 85% |
phenylethane 1,2-diol
carbon dioxide
2-methyl-but-3-yn-2-ol
A
4-Phenyl-1,3-dioxolan-2-one
B
3-Hydroxy-3-methyl-2-butanone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride In acetonitrile at 80℃; under 15001.5 Torr; for 24h; Autoclave; Sealed tube; chemoselective reaction; | A 98% B 91 %Chromat. |
With silver(l) oxide; N,N,N',N'-tetramethylguanidine In acetonitrile at 80℃; under 7500.75 Torr; for 12h; Autoclave; | A 95 %Spectr. B 97 %Spectr. |
Conditions | Yield |
---|---|
With N-chloro-succinimide; (neocuproine)Pd(OAc)2; sodium acetate In acetonitrile at 55℃; under 760.051 Torr; for 24h; Molecular sieve; | 97% |
With air; potassium iodide; palladium(II) iodide In ISOPROPYLAMIDE at 100℃; under 15201 Torr; for 15h; Autoclave; | 94% |
Stage #1: phenylethane 1,2-diol; carbon monoxide With sulfur; triethylamine In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 5h; Inert atmosphere; Autoclave; Stage #2: With copper(ll) bromide In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 16h; | 94% |
Conditions | Yield |
---|---|
With 2-Cyanopyridine; cerium(IV) oxide at 179.84℃; under 37503.8 Torr; for 48h; Autoclave; | 95% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 70℃; under 7500.75 Torr; for 18h; Autoclave; | 79% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1-dibromomethane at 70℃; under 7500.75 Torr; for 18h; Reagent/catalyst; Autoclave; Ionic liquid; | 79% |
Conditions | Yield |
---|---|
With γ-Fe2O3-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene nanoparticles (MNPs-TBD) at 125℃; for 10h; | 95% |
phenylethane 1,2-diol
2,2'-dipyridyl carbonate
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
In toluene at 110℃; for 0.5h; | 94% |
carbon dioxide
trimethylsulfoxonium iodide
benzaldehyde
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; dimethyl sulfoxide for 1h; Inert atmosphere; Stage #3: carbon dioxide In tetrahydrofuran; dimethyl sulfoxide at 40℃; under 760.051 Torr; for 6h; Inert atmosphere; | 94% |
phenylethane 1,2-diol
trifluoromethyl trifluoromethanesulfonate
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 1h; Reagent/catalyst; Sealed tube; | 94% |
Conditions | Yield |
---|---|
93.6% |
Conditions | Yield |
---|---|
With 4C33H15O6(3-)*6Zr(4+)*4O(2-)*4HO(1-)*4H2O; tetrabutylammomium bromide at 100℃; under 760.051 Torr; for 16h; Catalytic behavior; | 92.8% |
With carbon dioxide; pyrrolidine hydrochloride at 195℃; under 44130.5 Torr; | |
Multi-step reaction with 2 steps 1: COCl2; pyridine / Behandeln des Reaktionsgemisches mit NH3 in Benzol 2: water View Scheme | |
With potassium iodide; L-Tryptophan at 120℃; under 15001.5 Torr; for 2h; | 22 %Chromat. |
With ZnBr2 complex with hybrid polymer based on 5,5'-dibromo-2,2'-bipyridine and octavinylsilsesquioxane at 100℃; under 750.075 Torr; for 72h; Reagent/catalyst; Temperature; Schlenk technique; | 89 %Spectr. |
2-Bromo-1-phenylethanol
Tetramethylammonium hydrogen carbonate
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.25h; | 92% |
Conditions | Yield |
---|---|
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; | 90% |
With zinc(II) chloride at 160℃; under 112.511 Torr; for 3h; Ionic liquid; | 81.2% |
With 1-hexadecyl-3-methylimidazolium chloride; zinc(II) chloride In neat (no solvent) at 160℃; under 112.511 Torr; for 3h; Green chemistry; | 81.2% |
styrene
sodium hydrogencarbonate
A
4-Phenyl-1,3-dioxolan-2-one
B
2-Bromo-1-phenylethanol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 30℃; for 1h; Microwave irradiation; | A 6% B 89% |
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation; | A 70% B 20% |
phenylethane 1,2-diol
carbamic acid phenyl ester
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube; | 89% |
Conditions | Yield |
---|---|
at 25℃; under 750.075 Torr; for 24h; Inert atmosphere; Schlenk technique; | 89% |
With 1-carboxypropyl-imidazolium bromide at 120℃; under 11251.1 Torr; for 2h; | 86.85% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; acetone at 24 - 60℃; for 18h; Solvent; Microwave irradiation; | 86% |
styrene oxide
carbon dioxide
A
phenylethane 1,2-diol
B
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With cobalt 1,4-benzenedicarboxylate; 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide In neat (no solvent) at 70℃; under 760.051 Torr; for 27h; | A 9% B 85% |
With Zn(2,5-bis{N-(2,6-diisopropylphenyl)iminomethyl}pyrrole)2; tetrabutylammomium bromide at 105℃; under 760.051 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Schlenk technique; Inert atmosphere; | A n/a B 80% |
With C16H18Cl2CrN4(1+)*Cl(1-); tetra-(n-butyl)ammonium iodide In dichloromethane at 100℃; under 15001.5 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Autoclave; | A 12 %Chromat. B 79 %Chromat. |
styrene
sodium hydrogencarbonate
A
styrene oxide
B
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; acetone at 60℃; for 7.5h; Time; Microwave irradiation; | A 11% B 78% |
With N-Bromosuccinimide In water; acetone at 60℃; for 7.5h; Sealed tube; | A 45% B 37% |
carbon dioxide
toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Inert atmosphere; Glovebox; Green chemistry; | 77% |
styrene oxide
carbon dioxide
A
4-Phenyl-1,3-dioxolan-2-one
B
acetophenone
Conditions | Yield |
---|---|
With (2-hydroxyphenyl)diphenyl(propyl)phosphonium iodide In neat (no solvent) at 23℃; under 7500.75 Torr; for 24h; Autoclave; | A 74% B n/a |
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran for 2h; Heating; | 73% |
Conditions | Yield |
---|---|
With cobalt(II) nitrate hexahydrate; 2,5-dihydroxyterephthalohydrazide In dimethyl sulfoxide at 100℃; under 4500.45 Torr; for 5h; | 73% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetone at 85℃; under 6723.1 Torr; for 0.166667h; Flow reactor; |
styrene
sodium hydrogencarbonate
A
styrene oxide
B
4-Phenyl-1,3-dioxolan-2-one
C
2-Bromo-1-phenylethanol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water; acetone at 60℃; for 0.166667h; Time; Microwave irradiation; | A 15% B 9% C 73% |
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 80℃; for 1h; Microwave irradiation; | A 10% B 65% C 10% |
With N-Bromosuccinimide In water; acetone at 60℃; for 1h; Solvent; Microwave irradiation; | A 40% B 48% C 10% |
With N-Bromosuccinimide In water; acetone at 60℃; for 3h; Sealed tube; | A 47% B 36% C 8% |
With N-Bromosuccinimide In water; acetone at 60℃; for 1h; Sealed tube; | A 41% B 24% C 33% |
carbon dioxide
trimethylsulfoxonium iodide
benzaldehyde
A
4-Phenyl-1,3-dioxolan-2-one
B
2-iodo-1-phenylethan-1-ol
Conditions | Yield |
---|---|
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: benzaldehyde In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #3: carbon dioxide In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 12h; Inert atmosphere; | A 71% B 23% |
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: benzaldehyde In dimethyl sulfoxide for 1h; Inert atmosphere; Stage #3: carbon dioxide In dimethyl sulfoxide at 40℃; under 760.051 Torr; for 12h; Temperature; Inert atmosphere; | A 30% B 65% |
styrene
carbon dioxide
A
4-Phenyl-1,3-dioxolan-2-one
B
(1,2-dibromoethyl)benzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water under 15514.9 Torr; for 3h; | A 65% B 20% |
phenylethane 1,2-diol
1,1'-carbonyldiimidazole
4-Phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
In benzene for 3h; Heating; | 64% |
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 4h; Autoclave; | A > 99 %Chromat. B 99% |
With C23H21MnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 140℃; under 37503.8 Torr; for 16h; Autoclave; | A 95 %Chromat. B 99% |
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium carbonate In isopropyl alcohol at 140℃; Glovebox; | A 93 %Chromat. B 95% |
4-Phenyl-1,3-dioxolan-2-one
1-phenyl-2-phenylaminoethanol
3,5-diphenyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 130℃; for 19h; | 99% |
Conditions | Yield |
---|---|
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Pressure; Temperature; Sealed tube; Autoclave; | 95% |
With water; N,N'-dimethylimidazolium-2-carboxylate at 140℃; under 3000.3 Torr; for 24h; Autoclave; Sealed tube; | 90 %Chromat. |
Conditions | Yield |
---|---|
In ethyl acetate at 40℃; for 4h; | 94.1% |
The Phenylethylene carbonate, with the CAS registry number 4427-92-3, is also known as 1,3-Dioxolan-2-one, 4-phenyl-. This chemical's molecular formula is C9H8O3 and molecular weight is 164.16. What's more, both its IUPAC name and systematic name are the same which is called 4-Phenyl-1,3-dioxolan-2-one.
Physical properties about Phenylethylene carbonate are: (1)ACD/LogP: 0.312; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.31; (4)ACD/LogD (pH 7.4): 0.31; (5)ACD/BCF (pH 5.5): 1.02; (6)ACD/BCF (pH 7.4): 1.02; (7)ACD/KOC (pH 5.5): 35.21; (8)ACD/KOC (pH 7.4): 35.21; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.546; (14)Molar Refractivity: 41.62 cm3; (15)Molar Volume: 131.484 cm3; (16)Polarizability: 16.5×10-24 cm3; (17)Surface Tension: 43.735 dyne/cm; (18)Density: 1.249 g/cm3; (19)Flash Point: 171.072 °C; (20)Enthalpy of Vaporization: 59.99 kJ/mol; (21)Boiling Point: 354.821 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: c1ccc(cc1)C2COC(=O)O2
(2) InChI: InChI=1S/C9H8O3/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2
(3) InChIKey: ZKOGUIGAVNCCKH-UHFFFAOYSA-N
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