Product Name

  • Name

    Carbonic acid 1-phenylethylene ester

  • EINECS
  • CAS No. 4427-92-3
  • Article Data270
  • CAS DataBase
  • Density 1.249 g/cm3
  • Solubility
  • Melting Point 56-57 °C
  • Formula C9H8O3
  • Boiling Point 354.821 °C at 760 mmHg
  • Molecular Weight 164.161
  • Flash Point 171.072 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 4427-92-3 (Carbonic acid 1-phenylethylene ester)
  • Hazard Symbols
  • Synonyms 1-Phenyl-1, 2-ethylene carbonate;4-phenyl-1,3-dioxolan-2-one;Carbonic acid, cyclic phenylethylene ester;1,3-Dioxolan-2-one, 4-phenyl-;Cyclic phenylethylene carbonate;
  • PSA 35.53000
  • LogP 1.89450

Synthetic route

styrene oxide
96-09-3

styrene oxide

carbon dioxide
124-38-9

carbon dioxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
bis(phenyl) carbonate
102-09-0

bis(phenyl) carbonate

phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

Diethyl carbonate
105-58-8

Diethyl carbonate

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
styrene
292638-84-7

styrene

carbon dioxide
124-38-9

carbon dioxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
93-56-1

phenylethane 1,2-diol

carbon dioxide
124-38-9

carbon dioxide

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

A

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

B

3-Hydroxy-3-methyl-2-butanone
115-22-0

3-Hydroxy-3-methyl-2-butanone

Conditions
ConditionsYield
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.
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

carbon monoxide
201230-82-2

carbon monoxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

carbon dioxide
124-38-9

carbon dioxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

ethyl carbonate derivative

ethyl carbonate derivative

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
93-56-1

phenylethane 1,2-diol

2,2'-dipyridyl carbonate
1659-31-0

2,2'-dipyridyl carbonate

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
In toluene at 110℃; for 0.5h;94%
carbon dioxide
124-38-9

carbon dioxide

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

benzaldehyde
100-52-7

benzaldehyde

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
93-56-1

phenylethane 1,2-diol

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 1h; Reagent/catalyst; Sealed tube;94%
2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
93.6%
styrene oxide
96-09-3

styrene oxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
2425-28-7

2-Bromo-1-phenylethanol

Tetramethylammonium hydrogen carbonate
58345-96-3

Tetramethylammonium hydrogen carbonate

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;92%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

urea
57-13-6

urea

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
292638-84-7

styrene

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

A

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

B

2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

Conditions
ConditionsYield
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
93-56-1

phenylethane 1,2-diol

carbamic acid phenyl ester
622-46-8

carbamic acid phenyl ester

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube;89%
styrene oxide
96-09-3

styrene oxide

carbon monoxide
201230-82-2

carbon monoxide

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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%
styrene
292638-84-7

styrene

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With N-Bromosuccinimide In water; acetone at 24 - 60℃; for 18h; Solvent; Microwave irradiation;86%
styrene oxide
96-09-3

styrene oxide

carbon dioxide
124-38-9

carbon dioxide

A

phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

B

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
292638-84-7

styrene

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

A

styrene oxide
96-09-3

styrene oxide

B

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
124-38-9

carbon dioxide

toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester
40434-87-5, 40435-14-1, 127911-68-6, 40348-74-1

toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Inert atmosphere; Glovebox; Green chemistry;77%
styrene oxide
96-09-3

styrene oxide

carbon dioxide
124-38-9

carbon dioxide

A

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

B

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
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
phosgene
75-44-5

phosgene

phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 2h; Heating;73%
carbon dioxide
124-38-9

carbon dioxide

2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
292638-84-7

styrene

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

A

styrene oxide
96-09-3

styrene oxide

B

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

C

2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

Conditions
ConditionsYield
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
124-38-9

carbon dioxide

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

benzaldehyde
100-52-7

benzaldehyde

A

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
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
292638-84-7

styrene

carbon dioxide
124-38-9

carbon dioxide

A

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

B

(1,2-dibromoethyl)benzene
102921-26-6, 93-52-7

(1,2-dibromoethyl)benzene

Conditions
ConditionsYield
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
93-56-1

phenylethane 1,2-diol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

Conditions
ConditionsYield
In benzene for 3h; Heating;64%
4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

A

methanol
67-56-1

methanol

B

phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

Conditions
ConditionsYield
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
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

1-phenyl-2-phenylaminoethanol
99342-73-1, 31121-09-2

1-phenyl-2-phenylaminoethanol

3,5-diphenyl-1,3-oxazolidin-2-one
7426-72-4

3,5-diphenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 130℃; for 19h;99%
4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

Conditions
ConditionsYield
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.
pyrrolidine
123-75-1

pyrrolidine

4-Phenyl-1,3-dioxolan-2-one
4427-92-3

4-Phenyl-1,3-dioxolan-2-one

N-[(2-hydroxy-2-phenyl)ethyloxycarbonyl]pyrrolidine

N-[(2-hydroxy-2-phenyl)ethyloxycarbonyl]pyrrolidine

Conditions
ConditionsYield
In ethyl acetate at 40℃; for 4h;94.1%

Phenylethylene carbonate Specification

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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