Conditions | Yield |
---|---|
With sodium methylate Inert atmosphere; | 98% |
Stage #1: 1-(10H-phenoxazin-10-yl)ethan-1-one With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 24h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction; | 69% |
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; | 63% |
With sulfuric acid | |
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme |
phenoxazine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 155℃; for 0.25h; Microwave irradiation; chemoselective reaction; | 90% |
N -(2-(2-chlorophenoxy)phenyl)acetamide
phenoxazine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 155℃; for 0.25h; Microwave irradiation; chemoselective reaction; | 85% |
N-(2-(2-bromophenoxy)phenyl)acetamide
phenoxazine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 155℃; for 0.25h; Temperature; Solvent; Reagent/catalyst; Microwave irradiation; chemoselective reaction; | 83% |
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 100 °C / Microwave irradiation 2: caesium carbonate / N,N-dimethyl-formamide / 0.25 h / 155 °C / Microwave irradiation View Scheme |
N-(2-(2-iodophenoxy)phenyl)acetamide
phenoxazine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 155℃; for 0.25h; Microwave irradiation; chemoselective reaction; | 74% |
Multi-step reaction with 2 steps 1: potassium carbonate; N,N`-dimethylethylenediamine / toluene / 24 h / 135 °C / Inert atmosphere 2: sodium methylate / Inert atmosphere View Scheme |
phenoxazine
Conditions | Yield |
---|---|
With zinc | 73% |
phenoxazine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide electrolysis in 0.2M KClO4 with mercury pool working electrode, Ag/0.1M AgNO3 reference electrode, Pt counter electrode, potential -1.90 V; | 73% |
phenoxazine
Conditions | Yield |
---|---|
at 200 - 250℃; under 1 Torr; for 1h; | 48% |
N-(2-(2-bromophenoxy)phenyl)acetamide
A
1-(10H-phenoxazin-10-yl)ethan-1-one
B
phenoxazine
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 155℃; for 0.25h; Reagent/catalyst; Temperature; Microwave irradiation; | A 27% B 48% |
10-(α-methylbenzyl)phenoxazine
methyl iodide
A
phenoxazine
B
4-methyl-N-(α-phenylethyl)phenoxazine
C
4,6-dimethyl-N-(α-phenylethyl)phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium Product distribution; other 10-alkylphenoxazines, other electrophiles, various ratios of reagents, regiospecifity of lithiation; | A 2% B 40% C 5.5% |
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogenchloride at 240℃; Condensation; | A 8% B 39% |
Benzohydroxamic acid
A
N-phenyl benzoyl amide
B
phenoxazine
C
4-amino-phenol
D
aniline
E
2-amino-phenol
F
benzil
Conditions | Yield |
---|---|
at 240℃; for 0.5h; Product distribution; Mechanism; | A 11% B 4% C n/a D 32% E n/a F 2% |
Conditions | Yield |
---|---|
With calcium oxide at 560℃; | 18% |
cis-10-(1-Propenyl)phenoxazine
A
phenoxazine
B
1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenoxazine
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In ethyl acetate at 60℃; for 1.66667h; | A n/a B 13.5% |
Conditions | Yield |
---|---|
at 260℃; im mit Kohlendioxyd gefuellten Rohr und Behandeln des Reaktionsprodukts mit Alkohol und verd. Salzsaeure; | |
With 2-aminophenol hydrochloride at 220 - 230℃; | |
at 270℃; |
Conditions | Yield |
---|---|
at 200 - 240℃; | |
at 200 - 240℃; |
Conditions | Yield |
---|---|
With iodine at 270℃; | |
With hydrogenchloride |
10-Methyl-10H-phenoxazine
phenoxazine
Conditions | Yield |
---|---|
With Pyridine hydrobromide at 200℃; for 0.666667h; |
Conditions | Yield |
---|---|
With sulfuric acid; copper In ethanol Heating; |
diazomethane
carbon dioxide
10-(tert-butyldimethylsilyl)-phenoxazine
A
phenoxazine
B
methyl phenoxazine-4-carboxylate
C
10-(tert-Butyl-dimethyl-silanyl)-10H-phenoxazine-4-carboxylic acid methyl ester
D
dimethyl 10-(tert-butyldimethylsilyl)-phenoxazine-4,6-dicarboxylate
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
diazomethane
carbon dioxide
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
methyl phenoxazine-4-carboxylate
C
methyl N-(α-phenylethyl)phenoxazine-4-carboxylate
D
dimethyl 10-(α-methylbenzyl)phenoxazine-4,6-dicarboxylate
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
chloro-trimethyl-silane
10-(tert-butyldimethylsilyl)-phenoxazine
A
phenoxazine
B
10-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-10H-phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
chloro-trimethyl-silane
10-(tert-butyldimethylsilyl)-phenoxazine
A
phenoxazine
B
10-(tert-Butyl-dimethyl-silanyl)-4,6-bis-trimethylsilanyl-10H-phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
chloro-trimethyl-silane
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
10-(1-Phenyl-ethyl)-4-trimethylsilanyl-10H-phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
chloro-trimethyl-silane
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
10-(1-Phenyl-ethyl)-4-trimethylsilanyl-10H-phenoxazine
C
4,6-bis(trimethylsilyl)-10-(α-methylbenzyl)phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
Dimethyldisulphide
10-(tert-butyldimethylsilyl)-phenoxazine
A
phenoxazine
B
10-(tert-Butyl-dimethyl-silanyl)-4-methylsulfanyl-10H-phenoxazine
C
10-(tert-Butyl-dimethyl-silanyl)-4,6-bis-methylsulfanyl-10H-phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
Dimethyldisulphide
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
4-(methylthio)phenoxazine
C
4,6-bis(methylthio)phenoxazine
D
4,6-dimethylthio-N-(α-phenylethyl)phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
Dimethyldisulphide
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
4-(methylthio)-10-(α-methylbenzyl)phenoxazine
C
4,6-dimethylthio-N-(α-phenylethyl)phenoxazine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
carbon dioxide
10-(tert-butyldimethylsilyl)-phenoxazine
A
phenoxazine
B
10H-phenoxazine-4-carboxylic acid
C
10-(tert-Butyl-dimethyl-silanyl)-10H-phenoxazine-4-carboxylic acid
D
10-(tert-butyldimethylsilyl)-phenoxazine-4,6-dicarboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Multistep reaction; | |
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) 0 deg C, 1 h; Multistep reaction; |
carbon dioxide
10-(α-methylbenzyl)phenoxazine
A
phenoxazine
B
10-(1-Phenyl-ethyl)-10H-phenoxazine-4-carboxylic acid
C
10-(α-methylbenzyl)phenoxazine-4,6-dicarboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Multistep reaction; | |
With n-butyllithium 1.) THF, hexane, 0 deg C, 3 h, 2.) -78 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; chemoselective reaction; | 99% |
phenoxazine
2-phenyl-4,6-bis(p-bromophenyl)pyrimidine
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With Aliquat 336; sodium hydroxide In water Heating; | 98% |
phenoxazine
2,4,6-tris(4-bromophenyl)-1,3,5-triazine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene for 24h; Reflux; | 97% |
Stage #1: phenoxazine; 2,4,6-tris(4-bromophenyl)-1,3,5-triazine With potassium carbonate In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; palladium diacetate In toluene for 24h; Inert atmosphere; Reflux; | 96.5% |
phenoxazine
4,6-bis(4-bromophenyl)-2-methylpyrimidine
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; | 97% |
phenoxazine
7-bromo-2,3-diphenyl-5-azaquinoxaline
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 48h; | 97% |
With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; sodium t-butanolate In toluene Inert atmosphere; Reflux; | 97% |
Conditions | Yield |
---|---|
Stage #1: phenoxazine With tetraethylammonium bromide; potassium hydroxide In acetone at 50℃; for 1.5h; Inert atmosphere; Stage #2: 3-bromomethylheptane In acetone at 60℃; Inert atmosphere; | 97% |
With potassium hydroxide |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 48h; | 97% |
Conditions | Yield |
---|---|
With sodium ethanolate In N,N-dimethyl-formamide at 70 - 150℃; for 48h; | 97% |
With sodium hydride In hexane; N,N-dimethyl-formamide; mineral oil for 10h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide for 16h; Reflux; Inert atmosphere; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 0.14℃; for 48h; | 31.9% |
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide; sodium hydroxide In acetone Reflux; | 96% |
phenoxazine
1,3-bis-(4-bromobenzoyl)benzene
1,3-bis{4-(10H-phenoxazine-10-yl)benzoyl}benzene
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In toluene at 120℃; for 24h; Buchwald-Hartwig Coupling; | 96% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In acetonitrile at 20℃; for 12h; Irradiation; | 96% |
With ammonium peroxydisulfate; 2,4,6-triphenylpyrylium tetrafluoroborate In dichloromethane at 20℃; Irradiation; | 92% |
phenoxazine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene for 22h; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux; | 96% |
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene at 110℃; for 25h; Inert atmosphere; | 96% |
phenoxazine
2,4,6-tris(3-bromophenyl)-1,3,5-triazine
Conditions | Yield |
---|---|
Stage #1: phenoxazine; 2,4,6-tris(3-bromophenyl)-1,3,5-triazine With potassium carbonate In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With tri-tert-butyl phosphine; palladium diacetate In toluene for 24h; Inert atmosphere; Reflux; | 95.3% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere; | 95% |
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux; | 95% |
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere; | 76.8% |
phenoxazine
4,6-bis(4-bromophenyl)pyrimidine
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; | 95% |
phenoxazine
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 48h; | 95% |
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene Reflux; Inert atmosphere; | 93% |
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100℃; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene at 110 - 120℃; Inert atmosphere; | 95% |
With palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 110℃; for 24h; Inert atmosphere; | 82.6% |
phenoxazine
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 24h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: 4-(4-bromophenyl)-2,6-diphenylpyridine; phenoxazine With potassium carbonate In toluene for 0.25h; Inert atmosphere; Stage #2: With triisopropylamine; palladium diacetate In toluene for 48h; Reflux; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium carbonate at 130℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube; | 94% |
With N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; [Pd(π-cinnamyl)Cl]2 at 130℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 220℃; for 6h; Inert atmosphere; | 94% |
With copper(I) oxide In N,N-dimethyl acetamide at 160℃; for 24h; Inert atmosphere; | 90% |
With copper(I) oxide In N,N-dimethyl acetamide at 160℃; for 8h; | 90% |
phenoxazine
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; | 94% |
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 20 - 110℃; for 24h; Inert atmosphere; | 93.2% |
phenoxazine
5-bromo-10,15,20-tris(3,5-di-tert-butylphenyl)porphyrinato nickel(II)
Conditions | Yield |
---|---|
With C40H57Cl2N3Pd; sodium t-butanolate In tetrahydrofuran at 60℃; for 13h; Buchwald-Hartwig Coupling; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With oxygen; potassium carbonate In 1,2-dichloro-benzene at 130℃; for 3h; | 93% |
With oxygen; sodium nitrite In toluene at 0 - 20℃; Sealed tube; | 61% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 120℃; for 24h; Glovebox; Inert atmosphere; | 93% |
phenoxazine
Conditions | Yield |
---|---|
With ytterbium(III) triflate In 1,2-dichloro-ethane | 93% |
With ytterbium(III) triflate In 1,2-dichloro-ethane | 93% |
The IUPAC name of Phenoxazine is 10H-phenoxazine. With the CAS registry number 135-67-1 and EINECS 205-210-8, it is aslo named as 5,6-Dibenzo-1,4-oxazine. The product's categories are Phenylamine Series; Benzoxazines; Building Blocks; Heterocyclic Building Blocks; N-Containing; Others. It is grey to green-grey fine crystalline powder which is soluble in ether, benzene, mineral acid and almost insoluble in water. When using this chemical, people should not breathe dust and avoid contact with skin and eyes. Additionally, it should be sealed in the container.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.84; (4)ACD/LogD (pH 7.4): 3.84; (5)ACD/BCF (pH 5.5): 490.94; (6)ACD/BCF (pH 7.4): 491.04; (7)ACD/KOC (pH 5.5): 2936.41; (8)ACD/KOC (pH 7.4): 2936.99; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.624; (13)Molar Refractivity: 54.13 cm3; (14)Molar Volume: 153.1 cm3; (15)Polarizability: 21.46×10-24 cm3; (16)Surface Tension: 48.5 dyne/cm; (17)Enthalpy of Vaporization: 55.94 kJ/mol; (18)Vapour Pressure: 0.000372 mmHg at 25°C; (19)Exact Mass: 183.068414; (20)MonoIsotopic Mass: 183.068414; (21)Topological Polar Surface Area: 21.3; (22)Heavy Atom Count: 14; (23)Complexity: 187.
Uses of Phenoxazine: It is used as dyes intermediate. It is also used in organic synthesis and biochemical research. In addition, it can react with chloroacetyl chloride to get 10-chloroacetyl-10H-phenoxazine. This reaction needs solvent benzene by heating. The reaction time is 20 hours.
People can use the following data to convert to the molecule structure.
1. SMILES:O2c1ccccc1Nc3c2cccc3
2. InChI:InChI=1/C12H9NO/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
3. InChIKey:TZMSYXZUNZXBOL-UHFFFAOYAS
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