135-67-1

Basic information

• Product Name: Phenoxazine
• Synonyms: Phenoxazine 97%;Phenoxazine >=99%, purified by sublimation;10H-Phenoxazine (9CI);1H-Phenoxazine;10H-Phenoxazine;5,6-Dibenzo-1,4-oxazine;2,3,5,6-DIBENZO-1,4-OXAZINE;RARECHEM FH 2C 0S92
• CAS NO: 135-67-1
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• EINECS: 205-210-8
• Product Categories: Benzothiazoles;Phenylamine Series;Benzoxazines;Building Blocks;Heterocyclic Building Blocks;BenzoxazinesHeterocyclic Building Blocks;N-Containing;Others;organic
• Mol File: 135-67-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 156-159 °C(lit.)
• Boiling Point: 316.88°C (rough estimate)
• Flash Point: 122.6 °C
• Appearance: Gray to green-gray/Fine Crystalline Powder
• Density: 1.1261 (rough estimate)
• Vapor Pressure: 0.000372mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: benzene: freely soluble(lit.)
• PKA: 1.80±0.20(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• Merck: 14,7253
• BRN: 143234
• CAS DataBase Reference: Phenoxazine(CAS DataBase Reference)
• NIST Chemistry Reference: Phenoxazine(135-67-1)
• EPA Substance Registry System: Phenoxazine(135-67-1)

Safety Data

• Safety Statements: 22-24/25-25-24
• WGK Germany: 3
• RTECS: SP7450000
• Hazardous Substances Data: 135-67-1(Hazardous Substances Data)

Usage

General Description

Different sources of media describe the General Description of 135-67-1 differently. You can refer to the following data:
1. Phenoxazine (C12H9NO) is a heterocyclic compound whose structure consists of an oxazine bonded to 2 benzene rings. It forms the nucleus of a wide variety of pharmaceutical molecules and dye-stuffs. It is a grey to off-white powder with a purity of 98% that acts as a transitional agent for 4,6-bis(diphenylphosphino)phenazine, and it can also be applied as a transitional agent for catalysts, pharmaceuticals, and oled.
2. Phenoxazine dyes, including several Nile blue analogs, are known to localize selectively in animal tumors.

Properties

Phenoxazine has a molecular weight of 183.21 g/mol and a monoisotopic mass of 183.068 g/mol, which is also its exact mass. The compound has a heavy atom count of 14 and a complexity of 187. Phenoxazine has a melting point of 1560 C and it dissolves in water at the rate of 2.130 mg/l at 250 C

Uses

Different sources of media describe the Uses of 135-67-1 differently. You can refer to the following data:
1. Phenoxazine and its derivatives are not widely used hence the oxazine dyes are the only commercially viable derivatives. Certain oxazine dyes such as Nile blue dye is used in the preferential staining of brain cancer tissue since some of these dyes can inhibit the growth of these tumors. Various studies have explored the methods of preparation of boronic acids in a way that can result in a boron derivative of Phenoxazine (Nile blue dyes) which can be beneficial in cancer chemotherapy.
2. Phenoxazine is a tricyclic 2′deoxycytidine analog that has been used to improve stacking interactions between heterocycles of oligonucleotide/RNA hybrids and to enhance cellular uptake.

Preparation

The preparation of Phenoxazine and its by-products revolves around cyclization reactions. Each reaction is distinct from the other based on the starting materials and the conditions applied to the preparation process. Most cyclization reactions involved in the production of Phenoxazine and its by-products take place through one crucial step reactions as opposed to a series of steps where an aryl ether or an aryl amine would be obtained.

Hazards

The toxicological effects of Phenoxazine have not been investigated thoroughly but exposure to the compound may harm the eyes, skin, digestive tract and respiratory tract through irritation.

Chemical Properties

grey to green-grey fine crystalline powder

Purification Methods

Crystallise phenoxazine from EtOH and sublime it in vacuo. If too impure then extract it in a Soxhlet extractor using toluene. Evaporate the solvent and dissolve the residue (ca 100g) in *C6H6 (1L), CARCINOGEN (use an efficient fume cupboard) and chromatograph it through an Al2O3 column (50 x 450 mm) using *C6H6. The eluent (ca 3L) is evaporated to ca 150mL and cooled when ca 103g of phenoxazine m 149-153o is obtained. Sublimation yields platelets m 158-159o. It forms a green picrate m 141.5-142o. [Gilman & Moore J Am Chem Soc 79 3485 1957, Müller et al. J Org Chem 24 37 1959, Beilstein 27 I 223, 27 III/IV 1209.]

InChI:InChI=1/C12H9NO/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

Synthetic route

1-(10H-phenoxazin-10-yl)ethan-1-one (6192-43-4) → phenoxazine (135-67-1)

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

N -(2-(2-fluorophenoxy)phenyl)acetamide → phenoxazine (135-67-1)

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 (873977-74-3) → phenoxazine (135-67-1)

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 (204847-21-2) → phenoxazine (135-67-1)

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 (1370030-52-6) → phenoxazine (135-67-1)

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

C12H9NO(1+)*ClO4(1-) → phenoxazine (135-67-1)

Conditions	Yield
With zinc	73%

cyclopentadienyliron hexafluorophosphate of phenoxazine → phenoxazine (135-67-1)

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%

η6-phenoxazine-η5-cyclopentadienyliron hexafluorophosphate → phenoxazine (135-67-1)

Conditions	Yield
at 200 - 250℃; under 1 Torr; for 1h;	48%

N-(2-(2-bromophenoxy)phenyl)acetamide (204847-21-2) → 1-(10H-phenoxazin-10-yl)ethan-1-one (6192-43-4) + phenoxazine (135-67-1)

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 (113202-17-8) + methyl iodide (74-88-4) → phenoxazine (135-67-1) + 4-methyl-N-(α-phenylethyl)phenoxazine (113201-93-7) + 4,6-dimethyl-N-(α-phenylethyl)phenoxazine (113202-08-7)

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;

2-amino-phenol (95-55-6) → phenoxazine (135-67-1) + 2-(2-hydroxyphenlylamino)phenol (2391-71-1)

Conditions	Yield
With hydrogenchloride at 240℃; Condensation;	A 8% B 39%

Benzohydroxamic acid (495-18-1) → N-phenyl benzoyl amide (93-98-1) + phenoxazine (135-67-1) + 4-amino-phenol (123-30-8) + aniline (62-53-3) + 2-amino-phenol (95-55-6) + benzil (134-81-6)

Conditions	Yield
at 240℃; for 0.5h; Product distribution; Mechanism;	A 11% B 4% C n/a D 32% E n/a F 2%

2-phenoxyaniline (2688-84-8) → phenoxazine (135-67-1)

Conditions	Yield
With calcium oxide at 560℃;	18%

cis-10-(1-Propenyl)phenoxazine (123703-96-8) → phenoxazine (135-67-1) + 1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenoxazine (1186080-18-1)

Conditions	Yield
With boron trifluoride diethyl etherate In ethyl acetate at 60℃; for 1.66667h;	A n/a B 13.5%

benzene-1,2-diol (120-80-9) + 2-amino-phenol (95-55-6) → phenoxazine (135-67-1)

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℃;

2-aminophenol hydrochloride (51-19-4) + 2-amino-phenol (95-55-6) → phenoxazine (135-67-1)

Conditions	Yield
at 200 - 240℃;
at 200 - 240℃;

2-amino-phenol (95-55-6) → phenoxazine (135-67-1)

Conditions	Yield
With iodine at 270℃;
With hydrogenchloride

10-Methyl-10H-phenoxazine (25782-99-4) → phenoxazine (135-67-1)

Conditions	Yield
With Pyridine hydrobromide at 200℃; for 0.666667h;

[1,2,3]triazolo[4,5,1-kl]phenoxazine (202-27-7) → phenoxazine (135-67-1)

Conditions	Yield
With sulfuric acid; copper In ethanol Heating;

diazomethane (186581-53-3, 908094-01-9) + carbon dioxide (124-38-9) + 10-(tert-butyldimethylsilyl)-phenoxazine (113202-18-9) → phenoxazine (135-67-1) + methyl phenoxazine-4-carboxylate (100725-72-2) + 10-(tert-Butyl-dimethyl-silanyl)-10H-phenoxazine-4-carboxylic acid methyl ester (120033-13-8) + dimethyl 10-(tert-butyldimethylsilyl)-phenoxazine-4,6-dicarboxylate (120033-18-3)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

diazomethane (186581-53-3, 908094-01-9) + carbon dioxide (124-38-9) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + methyl phenoxazine-4-carboxylate (100725-72-2) + methyl N-(α-phenylethyl)phenoxazine-4-carboxylate (113202-06-5) + dimethyl 10-(α-methylbenzyl)phenoxazine-4,6-dicarboxylate (113202-07-6)

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

chloro-trimethyl-silane (75-77-4) + 10-(tert-butyldimethylsilyl)-phenoxazine (113202-18-9) → phenoxazine (135-67-1) + 10-(tert-Butyl-dimethyl-silanyl)-4-trimethylsilanyl-10H-phenoxazine (120033-12-7)

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 (75-77-4) + 10-(tert-butyldimethylsilyl)-phenoxazine (113202-18-9) → phenoxazine (135-67-1) + 10-(tert-Butyl-dimethyl-silanyl)-4,6-bis-trimethylsilanyl-10H-phenoxazine (120033-17-2)

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 (75-77-4) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + 10-(1-Phenyl-ethyl)-4-trimethylsilanyl-10H-phenoxazine (113201-94-8)

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 (75-77-4) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + 10-(1-Phenyl-ethyl)-4-trimethylsilanyl-10H-phenoxazine (113201-94-8) + 4,6-bis(trimethylsilyl)-10-(α-methylbenzyl)phenoxazine (120033-10-5)

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 (624-92-0) + 10-(tert-butyldimethylsilyl)-phenoxazine (113202-18-9) → phenoxazine (135-67-1) + 10-(tert-Butyl-dimethyl-silanyl)-4-methylsulfanyl-10H-phenoxazine (120033-11-6) + 10-(tert-Butyl-dimethyl-silanyl)-4,6-bis-methylsulfanyl-10H-phenoxazine (120033-15-0)

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 (624-92-0) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + 4-(methylthio)phenoxazine (113201-99-3) + 4,6-bis(methylthio)phenoxazine (113202-14-5) + 4,6-dimethylthio-N-(α-phenylethyl)phenoxazine (113202-10-1)

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 (624-92-0) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + 4-(methylthio)-10-(α-methylbenzyl)phenoxazine (113201-95-9) + 4,6-dimethylthio-N-(α-phenylethyl)phenoxazine (113202-10-1)

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 (124-38-9) + 10-(tert-butyldimethylsilyl)-phenoxazine (113202-18-9) → phenoxazine (135-67-1) + 10H-phenoxazine-4-carboxylic acid (99847-07-1) + 10-(tert-Butyl-dimethyl-silanyl)-10H-phenoxazine-4-carboxylic acid (113201-97-1) + 10-(tert-butyldimethylsilyl)-phenoxazine-4,6-dicarboxylic acid (263908-45-8)

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 (124-38-9) + 10-(α-methylbenzyl)phenoxazine (113202-17-8) → phenoxazine (135-67-1) + 10-(1-Phenyl-ethyl)-10H-phenoxazine-4-carboxylic acid (113202-20-3) + 10-(α-methylbenzyl)phenoxazine-4,6-dicarboxylic acid (113202-09-8)

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;

1,3,5-Trioxan (110-88-3) + phenoxazine (135-67-1) → 10-Methyl-10H-phenoxazine (25782-99-4)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; chemoselective reaction;	99%

phenoxazine (135-67-1) + 2-phenyl-4,6-bis(p-bromophenyl)pyrimidine (58536-47-3) → 4,6-bis(4-(10H-phenoxazin-10-yl)phenyl)-2-phenylpyrimidine

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere;	98%

1,4-dibromo-butane (110-52-1) + phenoxazine (135-67-1) → 10-(4-bromobutyl)-10H-phenoxazine

Conditions	Yield
With Aliquat 336; sodium hydroxide In water Heating;	98%

phenoxazine (135-67-1) + 2,4,6-tris(4-bromophenyl)-1,3,5-triazine (30363-03-2) → 2,4,6-tri(4-(10H-phenoxazin-10H-yl)phenyl)-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 (135-67-1) + 4,6-bis(4-bromophenyl)-2-methylpyrimidine (204589-02-6) → 4,6-bis(4-(10H-phenoxazin-10-yl)phenyl)-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 (135-67-1) + 7-bromo-2,3-diphenyl-5-azaquinoxaline (38870-31-4) → 2,3-diphenyl-7-(10H-phenoxazin-10-yl)pyrido[2,3-b]pyrazine

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%

2-ethylhexyl bromide (18908-66-2) + phenoxazine (135-67-1) → 10-(2-ethylhexyl)-10H-phenoxazine

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

phenoxazine (135-67-1) + C20H10Br3FN2 → C56H34FN5O3

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 48h;	97%

phenoxazine (135-67-1) + 2,6 difluorobenzonitrile (1897-52-5) → 2,6-di(10H-phenoxazin-10-yl)benzonitrile

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%

phenoxazine (135-67-1) + 4-fluorobenzaldehyde (459-57-4) → 4-(10H-phenoxazin-10-yl)benzaldehyde

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%

phenoxazine (135-67-1) + 1-dodecylbromide (143-15-7) → 10-dodecyl-10H-phenoxazine (1083062-16-1)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In acetone Reflux;	96%

phenoxazine (135-67-1) + 1,3-bis-(4-bromobenzoyl)benzene (136039-69-5) → 1,3-bis{4-(10H-phenoxazine-10-yl)benzoyl}benzene (1618669-36-5)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In toluene at 120℃; for 24h; Buchwald-Hartwig Coupling;	96%

3,4-dimethoxyphenol (2033-89-8) + phenoxazine (135-67-1) → C20H17NO4

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 (135-67-1) + 2,6-bis(4-chlorophenyl)isonicotinonitrile → 2,6-bis(4-(10H-phenoxazin-10-yl)phenyl)isonicotinonitrile

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 (135-67-1) + 2,4,6-tris(3-bromophenyl)-1,3,5-triazine (890148-78-4) → 2,4,6-tri(3-N-phenoxazylphenyl)-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%

bromobenzene (108-86-1) + phenoxazine (135-67-1) → 10-phenyl-10H-phenoxazine (37832-25-0)

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 (135-67-1) + 4,6-bis(4-bromophenyl)pyrimidine (141034-81-3) → 4,6-bis(4-(10H-phenoxazin-10-yl)phenyl)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 (135-67-1) + 2,3-bis(4′-bromophenyl)-6,7-difluoroquinoxaline → 10,10'-((6,7-difluoroquinoxaline-2,3-diyl)bis(4,1-phenylene))bis(10H-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%

phenoxazine (135-67-1) + 4-bromo-benzaldehyde (1122-91-4) → 4-(10H-phenoxazin-10-yl)benzaldehyde

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 (135-67-1) + 4-(4-chlorophenyl)-2,6-diphenylpyridine-3,5-dicarbonitrile → 4-(4-(10H-phenoxazin-10-yl)phenyl)-2,6-diphenylpyridine-3,5-dicarbonitrile

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 24h; Inert atmosphere;	95%

4-(4-bromophenyl)-2,6-diphenylpyridine (1498-81-3) + phenoxazine (135-67-1) → C35H24N2O

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%

phenoxazine (135-67-1) + tri-p-tert-butylphenol phosphate ester (78-33-1) → 10-(4-(tert-butyl)phenyl)-10H-phenoxazine

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%

phenoxazine (135-67-1) + methyl 4-iodobenzoate (619-44-3) → methyl 4-(10H-phenoxazin-10-yl)benzoate

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 (135-67-1) + 2',7'-dibromospiro[fluorene-9,9'-thioxanthene]-10',10'-dioxide → 2',7'-di(10H-phenoxazin-10-yl)spiro[fluorene-9,9'-thioxanthene]-10',10'-dioxide

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%

phenoxazine (135-67-1) + 4-bromo-N,N-bis-(4-methoxyphenyl)aniline (194416-45-0) → C32H26N2O3

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 20 - 110℃; for 24h; Inert atmosphere;	93.2%

phenoxazine (135-67-1) + 5-bromo-10,15,20-tris(3,5-di-tert-butylphenyl)porphyrinato nickel(II) (262424-49-7) → C74H79N5NiO

Conditions	Yield
With C40H57Cl2N3Pd; sodium t-butanolate In tetrahydrofuran at 60℃; for 13h; Buchwald-Hartwig Coupling; Inert atmosphere;	93%

2-phenyl-indole (948-65-2) + phenoxazine (135-67-1) → 10-(2-phenyl-1H-indol-3-yl)-10H-phenoxazine

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%

phenoxazine (135-67-1) + C36H27Br2N → C60H43N3O2

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 120℃; for 24h; Glovebox; Inert atmosphere;	93%

phenoxazine (135-67-1) + (1R,2S,6R)-2-(benzyloxy)-7-oxabicyclo[4.1.0]heptane → (1R,2S,6S)-2-(benzyloxy)-6-(10H-phenoxazin-10-yl)cyclohexan-1-ol

Conditions	Yield
With ytterbium(III) triflate In 1,2-dichloro-ethane	93%
With ytterbium(III) triflate In 1,2-dichloro-ethane	93%

Upstream product

• 6192-43-4 1-(10H-phenoxazin-10-yl)ethan-1-one 
• 120-80-9 benzene-1,2-diol 
• 95-55-6 2-amino-phenol 
• 624-92-0 Dimethyldisulphide 
• 113202-18-9 10-(tert-butyldimethylsilyl)-phenoxazine 
• 113202-17-8 10-(α-methylbenzyl)phenoxazine 
• 106-51-4 p-benzoquinone 
• 2688-84-8 2-phenoxyaniline 
• 27064-00-2 1-chloro-2-(2-nitrophenoxy)benzene 
• 108-95-2 phenol 
• 860465-22-1 1-iodo-2-(2-nitrophenoxy) benzene 
• 869790-15-8 2-(2-iodophenoxy)aniline 
• 95-56-7 2-hydroxybromobenzene 
• 93974-08-4 1-fluoro-2- (2-nitrophenoxy)benzene 

Downstream Products

• 18643-56-6 2-(4-Dicyanomethyl-phenyl)-malononitrile 
• 78028-07-6 α,α'-di(3-phenoxazinyl)-p-phenylenedimalononitrile 
• 42976-53-4 2-(4-Dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile; compound with 10H-phenoxazine 
• 73183-71-8 2-(10-Phenoxazinyl)benzoesaeure-methylester 
• 78028-10-1 α-(3-phenoxazinyl)-α'-<4-(N,N-dimethylaminophenyl)>-p-phenylenedimalononitrile 
• 113202-17-8 10-(α-methylbenzyl)phenoxazine 
• 73183-72-9 α,α-Dimethyl-2-(10-phenoxazinyl)benzolmethanol 
• 1416850-65-1 10-{4-[4-methoxy-2-(pyridin-2-yl)thiazol-5-yl]phenyl}-10H-phenoxazine 
• 1407632-07-8 PSB 12054 
• 1407484-53-0 C₂₁H₁₇NO₃ 
• 1407484-54-1 C₂₀H₁₄ClNO₃ 
• 1407484-55-2 C₂₀H₁₄N₂O₅ 
• 1407484-56-3 C₂₁H₁₇NO₄ 
• 1407484-57-4 C₂₁H₁₇NO₃ 

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Relevant articles and documents

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Microwave assisted rapid synthesis of phenoxazines and benzopyridoxazines

A facile protocol for the synthesis of phenoxazines and benzopyridoxazines by Smiles rearrangement have been demonstrated in short reaction time under microwave irradiation. The control experiments suggest that a reaction proceeds through Smiles rearrangement followed SNAr ring closure by in situ cascade process. In our present work, both the electron donating and electron withdrawing groups were tolerant and provided a corresponding phenoxazine/benzopyridoxazine in good to moderate yields.

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.

Characterization of HJ-PI01 as a novel Pim-2 inhibitor that induces apoptosis and autophagic cell death in triple-negative human breast cancer

Aim: Pim-2 is a short-lived serine/threonine kinase, which plays a key role in metastasis of breast cancer through persistent activation of STAT3. Although the crystal structure of Pim-2 has been reported, but thus far no specific Pim-2-targeted compounds have been reported. In this study, we identified a novel Pim-2 inhibitor, HJ-PI01, by in silico analysis and experimental validation. Methods: The protein-protein interaction (PPI) network, chemical synthesis, molecular docking, and molecular dynamics (MD) simulations were used to design and discover the new Pim-2 inhibitor HJ-PI01. The anti-tumor effects of HJ-PI01 were evaluated in human breast MDA-MB-231, MDA-MB-468, MDA-MB-436, MCF-7 cells in vitro and in MDA-MB-231 xenograft mice, which were treated with HJ-PI01 (40 mg·kg-1 ·d-1, ig) with or without lienal polypeptide (50 mg·kg-1 ·d-1, ip) for 10 d. The apoptosis/autophage-inducing mechanisms of HJ-PI01 were elucidated using Western blots, immunoblots, flow cytometry, transmission electron microscopy and fluorescence microscopy. Results: Based on the PrePPI network, the potential partners interacting with Pim-2 in regulating apoptosis (160 protein pairs) and autophagy (47 protein pairs) were identified. Based on the structural characteristics of Pim-2, a total of 15 compounds (HJ-PI01 to HJ-P015) were synthesized, which showed moderate or remarkable anti-proliferative potency in the human breast cancer cell lines tested. The most effective compound HJ-PI01 exerted a robust inhibition on MDA-MB-231 cells compared with chlorpromazine and the pan-Pim inhibitor PI003. Molecular dynamics (MD) simulation revealed that HJ-PI01 had a good binding score with Pim-2. Moreover, HJ-PI01 (300 nmol/L) induced death receptor-dependent and mitochondrial apoptosis as well as autophagic death in MDA-MB-231 cells. In MDA-MB-231 xenograft mice, administration of HJ-PI01 remarkably inhibited the tumor growth and induced tumor cell apoptosis in vivo. Co-administration of HJ-PI01 with lienal polypeptide could improve the anti-tumor activity of HJ-PI01 and reduce its toxicity. Conclusion: The newly synthesized compound, HJ-PI01, can induce death receptor/mitochondrial apoptosis and autophagic cell death by targeting Pim-2 in human breast cancer cells in vitro and in vivo.