Conditions | Yield |
---|---|
Stage #1: 9H-carbazol-4-ol With sodium hydroxide In water; isopropyl alcohol at 23 - 28℃; for 1h; Stage #2: epichlorohydrin In water; isopropyl alcohol at 20 - 40℃; for 15 - 20h; | 80.4% |
Stage #1: 9H-carbazol-4-ol With sodium hydroxide In water Stage #2: epichlorohydrin In water; dimethyl sulfoxide at 10 - 45℃; for 7h; | 80.5% |
Stage #1: 9H-carbazol-4-ol With sodium hydroxide In water; dimethyl sulfoxide at 10 - 30℃; for 0.25 - 0.333333h; Stage #2: epichlorohydrin at 10 - 30℃; for 25.5 - 30.75h; | 76.57% |
9H-carbazol-4-ol
epichlorohydrin
A
1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol
B
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With pyridine In isopropyl alcohol at 50 - 60℃; for 12h; Inert atmosphere; | A 80% B 10% |
With potassium carbonate In isopropyl alcohol at 50 - 60℃; for 12h; Inert atmosphere; | A 20% B 60% |
epichlorohydrin
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
Stage #1: 9H-carbazol-4-ol With sodium dithionite; potassium carbonate; potassium iodide In acetone for 1h; Heating / reflux; Stage #2: epichlorohydrin In acetone at 20℃; for 32h; Heating / reflux; | 69.9% |
9H-carbazol-4-ol
1,2-Epoxy-3-bromopropane
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 60℃; for 24h; | 60% |
With sodium hydroxide In water; dimethyl sulfoxide at 45℃; for 16h; | 31% |
Stage #1: 9H-carbazol-4-ol With sodium hydride In N,N-dimethyl-formamide Stage #2: 1,2-Epoxy-3-bromopropane In N,N-dimethyl-formamide | |
With potassium carbonate In butanone at 80℃; |
Conditions | Yield |
---|---|
With potassium carbonate In butanone |
9H-carbazol-4-ol
cefaloridine
dimethyl sulfoxide
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water; ethyl acetate |
(S)-oxirane-2-methyl methanesulfonate
9H-carbazol-4-ol
cefaloridine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water; dimethyl sulfoxide; ethyl acetate |
N-[2-(2'-(methoxy)-phenoxy)-ethyl]-benzylamine
4-(2,3-epoxypropoxy)carbazole
1-[benzyl[2(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)propan-2-ol
Conditions | Yield |
---|---|
With potassium carbonate In water at 20 - 90℃; for 3h; | 99% |
Stage #1: N-[2-(2'-(methoxy)-phenoxy)-ethyl]-benzylamine; 4-(2,3-epoxypropoxy)carbazole With zinc(II) chloride In ethyl acetate at 70 - 75℃; for 3h; Stage #2: With ammonia In water | |
With trifluoroacetic acid In 1,4-dioxane at 70 - 75℃; for 48h; |
benzylamine
4-(2,3-epoxypropoxy)carbazole
1-(9H-carbazol-4-yloxy)-3-phenylmethylamino-2-propanol
Conditions | Yield |
---|---|
In water at 60℃; for 10h; Product distribution / selectivity; | 98.7% |
at 40℃; for 1h; Temperature; | 97.79% |
In toluene Heating; | 72% |
In toluene Reflux; | 72% |
4-(2,3-epoxypropoxy)carbazole
methyl iodide
9-methyl-4-(oxiran-2-ylmethoxy)-9H-carbazole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 4h; | 97% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h; | 92% |
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h; | 81% |
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h; | 81% |
4-phenyl-1-piperazine
4-(2,3-epoxypropoxy)carbazole
1-((9H-carbazol-4-yl)oxy)-3-(4-phenylpiperazin-1-yl)propan-2-ol
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 97% |
In ethanol at 65℃; for 16h; | 80% |
In isopropyl alcohol for 5h; Inert atmosphere; Reflux; | 80% |
2-amino-2'-methoxydiphenyl ether
4-(2,3-epoxypropoxy)carbazole
N-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-2-(2-methoxyphenoxy)aniline
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 97% |
2,4-Dimethoxybenzylamine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
In ipa; ethyl acetate for 4.5h; Heating / reflux; | 94.2% |
1-iodo-propane
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h; | 93% |
1-phenylmethylpiperazine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 12h; Heating / reflux; | 92% |
In tetrahydrofuran for 12h; Product distribution / selectivity; Heating / reflux; | 92% |
tert-butylchlorodiphenylsilane
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With 4-methoxypyridine N-oxide; sodium sulfate In dichloromethane at 20℃; for 60h; regioselective reaction; | 92% |
carbon dioxide
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With C16H9MoN3O4; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 80℃; under 3750.38 Torr; for 20h; | 92% |
With C24H25N4O3(1+)*I(1-) In neat (no solvent) at 20℃; under 750.075 Torr; for 24h; Schlenk technique; | 76% |
With tetrabutylammomium bromide; C35H37CoN6O2(2+)*2Br(1-) In neat (no solvent) at 45℃; under 2250.23 Torr; for 24h; | 75% |
ethyl 3-(3-methoxyphenyl)-1H-pyrazole-5-carboxylate
4-(2,3-epoxypropoxy)carbazole
1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-(3-methoxyphenyl)-1H-pyrazole-5-carboxylic acid
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 80℃; for 32h; Inert atmosphere; | 90% |
4-Aminoacetophenone
4-(2,3-epoxypropoxy)carbazole
1-(4-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}phenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 58 - 62℃; for 8h; | 90% |
methyl 4-iodo-3-methylbenzoate
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With palladium diacetate; potassium bicyclo[2.2.1]hept-2-ene-5-carboxylate; XPhos In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; | 89% |
thiophenol
4-(2,3-epoxypropoxy)carbazole
1-(9H-carbazol-5-yloxy)-3-(phenylthio)propan-2-ol
Conditions | Yield |
---|---|
With dimethylbromosulphonium bromide at 20℃; for 0.25h; regioselective reaction; | 87% |
1-(2-Methoxyphenyl)piperazine
4-(2,3-epoxypropoxy)carbazole
1-((9H-carbazol-4-yl)oxy)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-ol
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 87% |
In isopropyl alcohol for 5h; Inert atmosphere; Reflux; | 72% |
1-methyl-2-o-methoxyphenoxyethylamine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
85% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 45h; | 85% |
With sodium hydride In tetrahydrofuran at 0℃; |
Conditions | Yield |
---|---|
With potassium (1S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylate; palladium diacetate; XPhos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; | 85% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium bicyclo[2.2.1]hept-2-ene-5-carboxylate; XPhos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h; | 85% |
Conditions | Yield |
---|---|
In ethanol at 65℃; for 72h; | 84% |
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 80℃; for 36h; Inert atmosphere; | 84% |
2-(2-methoxyphenoxy)propan-1-amine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
83% |
C10H15NO2
4-(2,3-epoxypropoxy)carbazole
1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxybenzyloxy)ethyl]amino}-2-propanol
Conditions | Yield |
---|---|
In isopropyl alcohol Reflux; | 82% |
In isopropyl alcohol Reflux; |
2-Amino-5-chlorobenzophenone
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 82% |
2-(2-methoxy-phenoxy)-ethylamine
4-(2,3-epoxypropoxy)carbazole
carvedilol
Conditions | Yield |
---|---|
In isopropyl alcohol for 5h; Inert atmosphere; Reflux; | 81% |
With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 80 - 85℃; | 36.26% |
With sulfuric acid; potassium carbonate In isopropyl alcohol at 80℃; for 6h; |
4-Aminobiphenyl
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 81% |
In isopropyl alcohol for 5h; Inert atmosphere; Reflux; | 73% |
1-(2-pyridyl)piperazine
4-(2,3-epoxypropoxy)carbazole
Conditions | Yield |
---|---|
In isopropyl alcohol for 5h; Inert atmosphere; Reflux; | 81% |
IUPAC Name: 4-(Oxiran-2-ylmethoxy)-9H-carbazole
Synonyms of 4-Epoxypropanoxycarbazole (CAS NO.51997-51-4): 4-(2,3-Epoxypropoxy)-carbazole
CAS NO: 51997-51-4
Molecular Formula: C15H13NO2
Molecular Weight: 239.27
Molecular Structure:
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 3
Polar Surface Area: 26.69 Å2
Index of Refraction: 1.729
Molar Refractivity: 71.89 cm3
Molar Volume: 180.2 cm3
Surface Tension: 63.1 dyne/cm
Density: 1.327 g/cm3
Flash Point: 166.4 °C
Enthalpy of Vaporization: 69.86 kJ/mol
Boiling Point: 464.9 °C at 760 mmHg
Vapour Pressure: 2.23E-08 mmHg at 25°C
Melting Point: 130-132°C
Appearance: pale yellow to almost white powder
SMILES: O(c3c1c(nc2ccccc12)ccc3)CC4OC4
InChI: InChI=1/C15H13NO2/c1-2-5-12-11(4-1)15-13(16-12)6-3-7-14(15)18-9-10-8-17-10/h1-7,10,16H,8-9H2 Copy
InChIKey: SVWKIGRDISDRLO-UHFFFAOYAD
Std. InChI: InChI=1S/C15H13NO2/c1-2-5-12-11(4-1)15-13(16-12)6-3-7-14(15)18-9-10-8-17-10/h1-7,10,16H,8-9H2 Std. InChIKey: SVWKIGRDISDRLO-UHFFFAOYSA-N
Product Categories of 4-Epoxypropanoxycarbazole (CAS NO.51997-51-4): Chemical intermediate for Benidipin;PHARMACEUTICAL INTERMEDIATES;(intermediate of carvedilol);Aromatics Compounds;Carbazoles;Oxiranes;Simple 3-Membered Ring Compounds;Carvedilol Intermediate;Aromatics
4-Epoxypropanoxycarbazole (CAS NO.51997-51-4) is used for the intermediate in the synthesis of carvedilol and Carazolol which are anti-hypertensive drug.
Hazard Codes: Xi
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