Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate; triethylamine In water for 1h; Irradiation; | 99% |
With pyridine; oxygen at 30℃; for 6.5h; UV-irradiation; | 39% |
With oxygen; sodium hydroxide In water at 20℃; for 2h; Irradiation; | 5% |
Conditions | Yield |
---|---|
With mixed-acid; sulfuric acid; nitric acid In cyclohexane; ethyl acetate; nitrobenzene | 94% |
With nitric acid | |
With nitric acid In sulfuric acid; water |
4-nitro-phenol
bis(trichloromethyl) carbonate
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 0℃; for 0.583333h; Inert atmosphere; | 91% |
With triethylamine In tetrahydrofuran for 2h; | 42% |
3-Hydroxy-3-phenyl-azocan-2-one
4-Nitrophenyl chloroformate
A
bis-(p-nitrophenyl) carbonate
B
1-aza-9,10-dioxo-8-oxa-7-phenylbicyclo<5.2.1>decane
Conditions | Yield |
---|---|
In toluene for 24h; Heating; | A 0.20 g B 90% |
4-Nitrophenyl chloroformate
A
bis-(p-nitrophenyl) carbonate
B
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With pyridine; hydrogenchloride In sodium hydroxide; chloroform | A 81% B n/a |
Conditions | Yield |
---|---|
In toluene at 60℃; for 3h; | 78% |
In benzene |
4-Nitrophenyl chloroformate
1,1'-bi-2-naphthol
A
bis-(p-nitrophenyl) carbonate
B
3,5-Dioxa-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-one
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃; for 1h; | A n/a B 78% |
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene at 20℃; for 0.25h; Green chemistry; | 74% |
With aluminum (III) chloride In toluene at 20℃; for 2h; | 70% |
Conditions | Yield |
---|---|
With pyridine In toluene; benzene | |
With pyridine In toluene | |
(i) Py, (ii) /BRN= 1098367/, toluene; Multistep reaction; |
Conditions | Yield |
---|---|
With ethyleneimine; triethylamine In diethyl ether | |
With pyridine In dichloromethane |
4-nitro-phenol
trichloromethyl chloroformate
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.166667h; Heating; Yield given; |
bis(phenyl) carbonate
nitric acid
A
bis-(p-nitrophenyl) carbonate
B
mononitrophenyl carbonate
Conditions | Yield |
---|---|
at -10 - -5℃; |
bis(phenyl) carbonate
nitric acid
A
bis-(p-nitrophenyl) carbonate
C
mononitrophenyl carbonate
Conditions | Yield |
---|---|
at -8℃; Product distribution; |
Conditions | Yield |
---|---|
With nitric acid at -8℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: Et3N, aziridine / diethyl ether View Scheme |
4-nitro-phenol
4-Nitrophenyl chloroformate
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 24h; Darkness; |
A
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium tert-butylate / dimethyl sulfoxide / 0.5 h / 80 °C / Inert atmosphere 2: triethylamine / dichloromethane / 24 h / Darkness View Scheme |
1-methylcyclopropanol
4-Nitrophenyl chloroformate
A
1-methylcyclopropyl (4-nitrophenyl)carbonate
B
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane-d2 at 20℃; |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 18h; Reflux; Green chemistry; | 239 mg |
bis-(p-nitrophenyl) carbonate
C17H20F3N3*ClH
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1.5h; | 100% |
piperidine
bis-(p-nitrophenyl) carbonate
(3R,4R,5R,7S)-5-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-hydroxypent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-7-[2-oxo-2-(propylamino)ethyl]-1,6-dioxaspiro[2.5]oct-4-yl acetate
(2S,3Z)-5-({(2R,3R,5S,6S)-6-[(2E,4E)-5-{(3R,4R,5R,7S)-4-(acetyloxy)-7-[2-oxo-2-(propylamino)ethyl]-1,6-dioxaspiro[2.5]oct-5-yl}-3-methylpenta-2,4-dien-1-yl]-2,5-dimethyltetrahydro-2H-pyran-3-yl}amino)-5-oxopent-3-en-2-yl piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: bis-(p-nitrophenyl) carbonate; (3R,4R,5R,7S)-5-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-hydroxypent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-7-[2-oxo-2-(propylamino)ethyl]-1,6-dioxaspiro[2.5]oct-4-yl acetate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Stage #2: piperidine In dichloromethane at 20℃; for 0.25h; | 100% |
bis-(p-nitrophenyl) carbonate
2-[2-(2-methoxyethoxy)ethoxy]ethylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 3h; | 100% |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Inert atmosphere; | 100% |
(8S,10S)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-10-(((1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4’,3’:4,5]oxazolo[2,3-c][1,4]oxazin-3-yl)oxy)-7,8,9,10-tetrahydrotetracene-5,5,12-dione
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; dichloromethane at 20℃; Darkness; | 100% |
bis-(p-nitrophenyl) carbonate
N-(6-azidohexanoyl)-Val-Cit-4-aminobenzyl alcohol
N-(6-azidohexanoyl)-Val-Cit-4-aminobenzyl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 41h; Inert atmosphere; | 99% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
Stage #1: bis-(p-nitrophenyl) carbonate; (3R,4S)-tert-butyl 3-(((S)-2-acetoxy-N-((R)-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)(tetrahydro-2H-pyran-4-yl)methyl)propanamido)methyl)-4-hydroxypyrrolidine-1-carboxylate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: n-Pentylamine In N,N-dimethyl-formamide at 20℃; for 1.5h; | 99% |
(2-methylpyridin-3-yl)methanol
bis-(p-nitrophenyl) carbonate
(2-methylpyridin-3-yl)methyl 4-nitrophenyl carbonate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In dichloromethane at 20℃; for 68h; | 98% |
bis-(p-nitrophenyl) carbonate
(2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)phenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 48h; | 98% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; | 93% |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 98% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl acetamide at 20℃; for 22h; Inert atmosphere; | 97% |
L-Valine methyl ester
bis-(p-nitrophenyl) carbonate
N-<<(4-nitrophenyl)oxy>carbonyl>-L-valine methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine In dichloromethane at 0℃; for 4h; | 96% |
With 4-methyl-morpholine In dichloromethane at 0℃; for 4h; | 96% |
bis-(p-nitrophenyl) carbonate
2-(4-nitrophenyl)ethylamine monohydrochloride
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 96% |
With triethylamine In N,N-dimethyl-formamide at 58 - 62℃; for 2h; Reagent/catalyst; Solvent; | 86% |
bis-(p-nitrophenyl) carbonate
allyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1- oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 1.5h; | 96% |
With N-ethyl-N,N-diisopropylamine at 20℃; for 13h; | 87% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15℃; for 3h; | 95.8% |
bis-(p-nitrophenyl) carbonate
A
carbon dioxide
B
bis(4-nitrophenyl)ether
Conditions | Yield |
---|---|
at 200 - 270℃; Product distribution; Kinetics; Mechanism; investigation of effect of iniciators and substituents in reactions; Ea= 26kcal/mol; | A n/a B 95% |
at 200 - 270℃; | A n/a B 95% |
Conditions | Yield |
---|---|
In dichloromethane for 4h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
In dichloromethane for 4h; Ambient temperature; | 95% |
6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide
bis-(p-nitrophenyl) carbonate
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; | 95% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; | 92% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 50℃; for 16h; | 95% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 3h; | 95% |
bis-(p-nitrophenyl) carbonate
hexan-1-ol
p-nitrophenylcarbonate hexyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25 - 30℃; | 94.84% |
bis-(p-nitrophenyl) carbonate
4-amino-3-deoxy-N10-formylpteroic acid
p-nitrophenyl 4-amino-4-deoxy-N10-formylpteroate
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 25℃; for 18h; | 94% |
oleylamine
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 20℃; for 3h; | 94% |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 144h; | 94% |
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 94% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 94% |
With triethylamine In tetrahydrofuran at 20℃; for 2h; | 77% |
Molecule structure of Bis(4-nitrophenyl) carbonate (CAS NO.5070-13-3):
IUPAC Name: Bis(4-nitrophenyl) carbonate
Molecular Weight: 304.21182 g/mol
Molecular Formula: C13H8N2O7
Density: 1.501 g/cm3
Melting Point: 136-139 °C(lit.)
Boiling Point: 475.9 °C at 760 mmHg
Flash Point: 217.5 °C
Index of Refraction: 1.632
Molar Refractivity: 72.3 cm3
Molar Volume: 202.6 cm3
Surface Tension: 63.4 dyne/cm
Enthalpy of Vaporization: 73.95 kJ/mol
Vapour Pressure: 3.19E-09 mmHg at 25 °C
Sensitive: moisture sensitive
XLogP3-AA: 3.3
H-Bond Acceptor: 7
Rotatable Bond Count: 4
Exact Mass: 304.033151
MonoIsotopic Mass: 304.033151
Topological Polar Surface Area: 122
Heavy Atom Count: 22
Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC(=O)OC2=CC=C(C=C2)[N+](=O)[O-]
InChI: InChI=1S/C13H8N2O7/c16-13(21-11-5-1-9(2-6-11)14(17)18)22-12-7-3-10(4-8-12)15(19)20/h1-8H
InChIKey: ACBQROXDOHKANW-UHFFFAOYSA-N
EINECS: 225-775-4
Product Categories of Bis(4-nitrophenyl) carbonate (CAS NO.5070-13-3): Industrial/Fine Chemicals
Hazard Codes: Xi
Risk Statements: 36/38
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 10-21
Bis(4-nitrophenyl) carbonate (CAS NO.5070-13-3) is also named as 4,4'-Dinitrodiphenyl carbonate ; AI3-14990 ; Bis(p-nitrophenyl) carbonate ; NSC 1730 ; p,p'-Dinitrodiphenylcarbonate . Bis(4-nitrophenyl) carbonate (CAS NO.5070-13-3) is white to pale yellow or beige powder.
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