Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate; triethylamine In water for 1.5h; Irradiation; | 99% |
With pyridine; oxygen at 20℃; for 1h; Time; Reagent/catalyst; Irradiation; | 99% |
tetrabutyl phosphonium bromide
phenyl chloroformate
carbonic acid dimethyl ester
bis(phenyl) carbonate
Conditions | Yield |
---|---|
98% |
methyl phenyl carbonate
tetrabutyl phosphonium bromide
phenyl chloroformate
bis(phenyl) carbonate
Conditions | Yield |
---|---|
98% |
3,3'-carbonylbis<5-phenyl-1,3,4-oxadiazole-2(3H)-thione>
phenol
A
bis(phenyl) carbonate
B
5-phenyl-1,3,4-oxadiazole-2(3H)-thione
Conditions | Yield |
---|---|
With pyridine In various solvent(s) for 192h; Ambient temperature; | A 97% B n/a |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; N,N-dimethyl-formamide | A 97% B n/a |
carbonic acid dimethyl ester
phenol
A
bis(phenyl) carbonate
B
methanol
Conditions | Yield |
---|---|
lead (II) phenoxide at 210 - 235℃; under 150.015 - 6750.68 Torr; for 500 - 6000h; Product distribution / selectivity; Heating / reflux; | A 97% B n/a |
Conditions | Yield |
---|---|
With trifluoroacetyl peroxide; trifluoroacetic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -25℃; for 1h; Criegee rearrangement; | 96% |
benzophenone diphenyl ketal
bis(phenyl) carbonate
Conditions | Yield |
---|---|
With trifluoroacetyl peroxide; trifluoroacetic acid In trichlorofluoromethane at -24℃; for 1h; Criegee rearrangement; | 96% |
N,N′-hexanediyl bis-carbamic acid diphenyl ester
A
bis(phenyl) carbonate
B
Hexamethylene diisocyanate
Conditions | Yield |
---|---|
at 150℃; under 11.2511 - 112.511 Torr; | A n/a B 95.3% |
Conditions | Yield |
---|---|
With hydrogenchloride | 95.2% |
With hydrogenchloride | 95.2% |
With hydrogenchloride | 95.2% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; oxygen at 65℃; under 36003.6 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Autoclave; | 95% |
With oxygen; tetrabutyl phosphonium bromide; p-benzoquinone; palladium diacetate; cerium(III) acetate In 1,2-propylene cyclic carbonate at 25 - 100℃; under 45004.5 - 47254.7 Torr; for 3h; Product distribution / selectivity; | 70% |
With oxygen; tetrabutyl phosphonium bromide; p-benzoquinone; palladium diacetate; cerium(III) acetate In 1,2-propylene cyclic carbonate at 25 - 100℃; under 45004.5 - 47254.7 Torr; for 3h; Product distribution / selectivity; | 55% |
diphenylthiocarbonate
bis(phenyl) carbonate
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In tetrachloromethane; acetonitrile at 0℃; for 12h; | 94% |
With hydrogenchloride; N-nitrosopiperidine; potassium iodide In hydrogenchloride; dichloromethane; water at 22℃; for 43h; | 78% |
With hydrogenchloride; sodium nitrite In dichloromethane; water at 45℃; for 20h; | 15 % Chromat. |
phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate
phenol
bis(phenyl) carbonate
Conditions | Yield |
---|---|
With aluminum (III) chloride In toluene at 20℃; for 0.25h; | 94% |
With potassium tert-butylate In toluene at 20℃; for 0.25h; Green chemistry; | 80% |
tetrakis(triphenylphosphine) palladium(0)
Phenyl cyanoformate
A
bis(phenyl) carbonate
Conditions | Yield |
---|---|
In toluene byproducts: CO; under Ar; NCCOOPh added to toluene dispersion of Pd(PPh3)4 at room temp.; stirred for 48 h; filtered; solid washed with hexane; dried under vac.; detd. by (1)H and (31)P NMR spectra; | A 92% B 83% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane Condensation; | 90% |
In pyridine; dichloromethane | 90% |
N,N,N',N'-tetramethylchlorformamidinium chloride at 86.9℃; for 24h; |
Conditions | Yield |
---|---|
With 1H-imidazole; potassium carbonate at 95℃; under 750.075 Torr; for 9h; Time; Inert atmosphere; | 90% |
With di(n-butyl)tin oxide at 180 - 200℃; for 12h; Inert atmosphere; | 18.6% |
methyl phenyl carbonate
bis(phenyl) carbonate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate at 180℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Green chemistry; | 90% |
at 160℃; under 375.038 Torr; for 3h; Temperature; | 81.9% |
With N,N,N-triethyl-N-butanesulfonic acid ammonium hydrogen sulfate at 160℃; under 375.038 Torr; for 3h; Reagent/catalyst; Temperature; Pressure; Ionic liquid; | 81.9% |
Conditions | Yield |
---|---|
Stage #1: phenol; pyridine at 50 - 150℃; Heating / reflux; Stage #2: phosgene at 150℃; | A 89.9% B n/a |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 72h; Reagent/catalyst; Sealed tube; | 88% |
Conditions | Yield |
---|---|
With copper(I) bromide; lithium bromide In tetrahydrofuran at 20℃; | A n/a B 84% |
Conditions | Yield |
---|---|
Pt/Al2O3 at 300℃; | A 15% B 80% |
aluminum oxide In toluene at 400℃; | A 40% B 5% |
Conditions | Yield |
---|---|
With disodium telluride; tetrabutylammomium bromide In water; benzene for 0.25h; Ambient temperature; | 77% |
With aluminum (III) chloride; butan-1-ol In toluene Reagent/catalyst; Temperature; Reflux; | 20% |
With diethyl ether; magnesium ethylate |
phenylpropiolic acid sodium salt
phenyl chloroformate
A
bis(phenyl) carbonate
B
phenyl 3-phenyl-2-propynoate
C
4-phenylnaphtho[2,3-c]furan-1,3-dione
Conditions | Yield |
---|---|
In tetrahydrofuran at 40 - 67℃; | A n/a B n/a C 73% |
methyl phenyl carbonate
A
bis(phenyl) carbonate
B
carbonic acid dimethyl ester
Conditions | Yield |
---|---|
With SiO2 supported 15 wt% MoO3 at 200℃; for 2h; Kinetics; Reagent/catalyst; Inert atmosphere; | A 71.4% B n/a |
catalyst C at 195℃; under 225.023 Torr; Product distribution / selectivity; | |
titanium(IV) phenoxide at 195℃; under 225.023 Torr; Product distribution / selectivity; |
2-chlorocarbonyloxy-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane
phenol
bis(phenyl) carbonate
Conditions | Yield |
---|---|
With triethylamine In diethyl ether for 24h; | 70% |
sodium propargylate
phenyl chloroformate
A
bis(phenyl) carbonate
B
phenyl prop-2-ynoate
Conditions | Yield |
---|---|
In tetrahydrofuran at 25 - 40℃; for 2h; Substitution; | A n/a B 70% |
Conditions | Yield |
---|---|
With iron(III) nitrate hexahydrate; nitric acid In tetrahydrofuran at 70℃; | 70% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In dimethyl sulfoxide at 25℃; Kinetics; | A 100% B n/a |
Conditions | Yield |
---|---|
With 4-nitro-benzoic acid In toluene at 80℃; for 16h; Reagent/catalyst; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: bis(phenyl) carbonate; uridine In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate at 115℃; for 4h; | 100% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide for 4.5h; Reflux; | 100% |
bis(phenyl) carbonate
1,6-Hexanediamine
N,N′-hexanediyl bis-carbamic acid diphenyl ester
Conditions | Yield |
---|---|
With lead(II) oxide In phenol at 50℃; Product distribution / selectivity; Industry scale; | 99.5% |
With phenol at 50℃; Product distribution / selectivity; Industry scale; | 99.5% |
With phenol at 50℃; Industrial scale; | 99.5% |
bis(phenyl) carbonate
3-aminomethyl-3,5,5-trimethylcyclohexylamine
3-(phenoxycarbonylamino-methyl)-3,5,5-trimethylcyclohexyl carbamic acid phenyl ester
Conditions | Yield |
---|---|
With lead(II) oxide In phenol at 50℃; Product distribution / selectivity; Industry scale; | 99.3% |
lead(II) oxide In phenol at 50℃; Industry scale; | 99.3% |
With phenol at 50℃; Product distribution / selectivity; Industry scale; | 99.3% |
In phenol at 50℃; | 99.3% |
In phenol | 93% |
bis(phenyl) carbonate
4,4'-diaminodicyclohexylmethane
phenyl N-[4-({4-[(phenoxycarbonyl)amino]cyclohexyl}methyl)cyclohexyl]carbamate
Conditions | Yield |
---|---|
With iron(II) diacetylacetonate In phenol at 50℃; Product distribution / selectivity; Industry scale; | 99.1% |
With phenol; ferrous acetylacetonate at 50℃; Product distribution / selectivity; Industry scale; | 99.2% |
With iron(II) acetylacetonate In phenol at 50℃; Reagent/catalyst; | 99.1% |
In phenol Large scale; | 95% |
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 10h; Autoclave; | 99% |
With calcium carbide; caesium carbonate In water; dimethyl sulfoxide at 140℃; for 16h; Inert atmosphere; Green chemistry; | 74% |
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave; | 64% |
bis(phenyl) carbonate
1,6-Hexanediamine
phenol
N,N′-hexanediyl bis-carbamic acid diphenyl ester
Conditions | Yield |
---|---|
at 45 - 60℃; for 1.33333h; Product distribution / selectivity; | 99% |
at 50 - 60℃; for 1.33333h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile at 20 - 120℃; for 24h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; regioselective reaction; | 99% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 59.84℃; for 3h; | 76% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In neat (no solvent) at 59.84℃; for 3h; Temperature; Time; Concentration; Inert atmosphere; Green chemistry; regioselective reaction; | |
With polystyrene-supported 1,8-diazabicyclo[5.4.0]-undec-7-ene In neat (no solvent) at 159.84℃; for 4h; Temperature; Time; Inert atmosphere; Schlenk technique; |
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 |
---|---|
In tetrahydrofuran; water at 20℃; for 3h; | 99% |
In tetrahydrofuran; water at 20℃; for 8h; | 85% |
In neat (no solvent) at 80℃; for 0.166667h; |
bis(phenyl) carbonate
cis-1,2-cyclopentanediol
(3aR,6aS)-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-2-one
Conditions | Yield |
---|---|
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 3h; | 99% |
bis(phenyl) carbonate
4,4'-diamino diphenyl methane
N,N'-(4,4'-methanediyl-di-phenyl)-bis-carbamic acid diphenyl ester
Conditions | Yield |
---|---|
With zinc(II) acetate dihydrate at 50℃; Product distribution / selectivity; Industry scale; | 98.8% |
With phenol; zinc(II) acetate dihydrate at 50℃; Product distribution / selectivity; Industry scale; | 98.8% |
With isobutyric Acid; 1,3,5-tris(N,N-dimethylaminopropyl)-hexahydro-s-triazine In toluene at 55℃; for 48h; | 96.4% |
With diphenyl-phosphinic acid at 89.85℃; for 7h; Acylation; | 91% |
bis(phenyl) carbonate
4-methylbenzene-1,3-diamine
toluene-2,4-dicarbamic acid diphenyl ester
Conditions | Yield |
---|---|
With zinc(II) acetate dihydrate at 50℃; Industry scale; | 98.1% |
With zinc(II) acetate dihydrate; phenol at 50℃; Industry scale; | 98.1% |
With zinc(II) acetate dihydrate In phenol at 50℃; | 98.1% |
Conditions | Yield |
---|---|
With isobutyric Acid; 1,3,5-tris(N,N-dimethylaminopropyl)-hexahydro-s-triazine In toluene at 55℃; for 48h; | 98% |
With diphenyl-phosphinic acid In tetrahydrofuran at 69.9℃; for 20h; | 51% |
With diphenyl-phosphinic acid In tetrahydrofuran at 89.84℃; for 20h; | 50% |
With isobutyric Acid In neat (no solvent) at 80℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 96h; | 98% |
With pyridine at 140 - 150℃; for 6h; Esterification; | 92% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In neat (no solvent) at 160℃; for 24h; Green chemistry; | 73% |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; | 98% |
bis(phenyl) carbonate
1h-benzotriazole-5-carboxylic acid
N,N-dimethyl-formamide
5-phenoxycarbonylbenzotriazole
Conditions | Yield |
---|---|
With sodium carbonate | 98% |
bis(phenyl) carbonate
efavirenz
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 2h; | 98% |
bis(phenyl) carbonate
(2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol
efavirenz
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20 - 60℃; for 2h; | 98% |
bis(phenyl) carbonate
dmap
4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide
(Z)-4-(dimethylamino)-N-((4-(5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)sulfonyl)pyridin-1-ium-1-carbimidate
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.166667h; | 98% |
bis(phenyl) carbonate
N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine
Conditions | Yield |
---|---|
In toluene at 20℃; | 98% |
bis(phenyl) carbonate
2-[2-(2-methoxyethoxy)ethoxy]ethylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine for 3h; Reflux; | 98% |
bis(phenyl) carbonate
1,4-phenylenediamine
1,4-phenylene bis-phenylcarbamate
Conditions | Yield |
---|---|
With isobutyric Acid; 1,3,5-tris(N,N-dimethylaminopropyl)-hexahydro-s-triazine In toluene at 55℃; for 48h; | 98% |
Reported in EPA TSCA Inventory.
The Diphenyl carbonate, also known as Carbonic acid, diphenyl ester, is the organic compound with the formula C13H10O3. This chemical belongs to the product categories of Color Former & Related Compounds; Functional Materials; Sensitizer; Carbonates; Carbonyl Compounds; Organic Building Blocks. Its EINECS registry number is 203-005-8. With the CAS registry number 102-09-0, its IUPAC name is called Diphenyl carbonate. It is both as a monomer in combination with bisphenol A in the production of polycarbonate polymers and a product of the decomposition of polycarbonates.
Physical properties of Diphenyl carbonate: (1)ACD/LogP: 3.28; (2)ACD/LogD (pH 5.5): 3.28; (3)ACD/LogD (pH 7.4): 3.28; (4)ACD/BCF (pH 5.5): 183.15; (5)ACD/BCF (pH 7.4): 183.15; (6)ACD/KOC (pH 5.5): 1449.84; (7)ACD/KOC (pH 7.4): 1449.84; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.575; (11)Molar Refractivity: 59.21 cm3; (12)Molar Volume: 178.9 cm3; (13)Surface Tension: 44 dyne/cm; (14)Density: 1.197 g/cm3; (15)Flash Point: 119.4 °C; (16)Enthalpy of Vaporization: 54.43 kJ/mol; (17)Boiling Point: 304 °C at 760 mmHg; (18)Vapour Pressure: 0.000899 mmHg at 25°C.
Preparation: this chemical can be prepared by carbonic acid dimethyl ester and phenol. This reaction is a kind of transesterification. It will need catalyst TiO2/SiO2. The reaction pressure is 0.39 MPan with reaction temperature of 200~250 °C.
Uses of Diphenyl carbonate: it is mainly used as synthetic raw material for engineering plastic polycarbonate and gathering p-hydroxy benzoic acid ester. In addition, it can also be used as plasticizer and solvents of nitric acid cellulose.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful if swallowed. Meanwhile, is is harmful by inhalation. You should not breathe its dust. What's more, you must avoid contact it with skin and eyes.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)OC(=O)OC2=CC=CC=C2
(2)InChI: InChI=1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
(3)InChIKey: ROORDVPLFPIABK-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 1500mg/kg (1500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | National Technical Information Service. Vol. OTS0540144, |
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