Product Name

  • Name

    Phenothiazine

  • EINECS 202-196-5
  • CAS No. 92-84-2
  • Article Data124
  • CAS DataBase
  • Density 1.233 g/cm3
  • Solubility water: 2 mg/L (25 °C)
  • Melting Point 184 °C
  • Formula C12H9NS
  • Boiling Point 371.003 °C at 760 mmHg
  • Molecular Weight 199.276
  • Flash Point 178.176 °C
  • Transport Information
  • Appearance yellow or pale green powder
  • Safety 26-61-36/37/39-29-22
  • Risk Codes 36/37/38-43-51/53-40-20/21/22
  • Molecular Structure Molecular Structure of 92-84-2 (Phenothiazine)
  • Hazard Symbols IrritantXi,DangerousN,HarmfulXn
  • Synonyms Phenothiazine(6CI,7CI,8CI);Antage TDP;Contaverm;Danikoropa;Dibenzo-1,4-thiazine;Dibenzothiazine;ENT 38;Early bird wormer;Feeno;Fenoverm;NSC 2037;Nemazene;Nexarbol;Orimon;Phenegic;Phenoverm;Phenovis;Phenoxur;Phenzeen;Reconox;Thiodiphenylamine;
  • PSA 37.33000
  • LogP 4.03280

Synthetic route

10-(1-methoxy-2-propynyl)phenothiazine

10-(1-methoxy-2-propynyl)phenothiazine

A

Propargylic aldehyde
624-67-9

Propargylic aldehyde

B

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 18℃;A n/a
B 95%
10-acetyl-10H-phenothiazine
1628-29-1

10-acetyl-10H-phenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With potassium tert-butylate In ethyl acetate at 20℃; for 2h;95%
Stage #1: 10-acetyl-10H-phenothiazine 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;		77%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;73%
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
10-vinyl-10H-phenothiazine
19210-66-3

10-vinyl-10H-phenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With p-benzoquinone In ethanol at 60℃; for 10h; Rate constant; Thermodynamic data; electron-Affinity Energy; other electron acceptor;94%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
Stage #1: 1-Bromo-2-iodobenzene; 2-amino-benzenethiol With ferric citrate In N,N-dimethyl-formamide at 80℃; for 2h; Green chemistry;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Green chemistry; regioselective reaction;		94%
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere; regioselective reaction;91%
With potassium phosphate; copper(l) iodide; N',N'-diphenyl-1H-pyrrole-2-carbohydrazide In diethylene glycol at 90℃; for 7h; Sealed tube;70%
With N-methoxy-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; potassium hydroxide at 90℃; for 15h; Sealed tube;64%
10-acetyl-10H-phenothiazine
1628-29-1

10-acetyl-10H-phenothiazine

A

10H-phenothiazine
92-84-2

10H-phenothiazine

B

10-acetoacetylphenothiazine
76331-03-8

10-acetoacetylphenothiazine

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran for 24h; Ambient temperature;A n/a
B 92%
With n-butyl magnesium bromide In tetrahydrofuran for 20h; Ambient temperature;A 90%
B n/a
With n-butyllithium In tetrahydrofuran for 20h; Product distribution; Ambient temperature; Effect of various organometallic reagents (n-BuMgBr, LiTMP, n-BuLi).;A n/a
B 71%
2-chlorophenothiazine
92-39-7

2-chlorophenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With isopropyl alcohol In N,N-dimethyl-formamide at 20℃; for 36h; UV-irradiation; chemoselective reaction;91%
In water; acetonitrile Quantum yield; Photolysis;90%
1,2-Diiodobenzene
615-42-9

1,2-Diiodobenzene

thioacetic acid S-(2-acetylamino-phenyl)ester
1204-55-3

thioacetic acid S-(2-acetylamino-phenyl)ester

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;91%
diphenylamine
122-39-4

diphenylamine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With iodine In acetone for 0.05h; Irradiation;90%
With iodine; sulfur83%
With sulfur at 110 - 145℃; Temperature; Inert atmosphere;81.1%
(E)-3-(10H-phenothiazin-10-yl)propenal

(E)-3-(10H-phenothiazin-10-yl)propenal

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In acetonitrile at 20℃; for 0.5h;90%
Phenothiazine-10-carboxylic acid 4-diethylamino-butyl ester
72332-01-5

Phenothiazine-10-carboxylic acid 4-diethylamino-butyl ester

A

1-ethylpyrrolidine
7335-06-0

1-ethylpyrrolidine

B

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
at 200℃; for 0.5h; Yields of byproduct given;A n/a
B 89%
2-bromo-N-(2-iodophenyl)aniline
1286730-54-8

2-bromo-N-(2-iodophenyl)aniline

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; thioacetamide In water; dimethyl sulfoxide at 120℃; for 20h; Inert atmosphere;89%
sulfoxyde de phenothiazine
1207-71-2

sulfoxyde de phenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 120℃; under 5320.36 Torr; for 24h;87%
Phenothiazine-10-carboxylic acid 5-diethylamino-pentyl ester
72332-03-7

Phenothiazine-10-carboxylic acid 5-diethylamino-pentyl ester

A

1-ethyl-piperidine
766-09-6

1-ethyl-piperidine

B

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
at 170 - 210℃; Yields of byproduct given;A n/a
B 83%
10-(N'-phenylchloroformimidoyl)phenothiazine
127832-97-7

10-(N'-phenylchloroformimidoyl)phenothiazine

O,O-diisopropyl hydrogen phosphorodithioate
107-56-2

O,O-diisopropyl hydrogen phosphorodithioate

A

10H-phenothiazine
92-84-2

10H-phenothiazine

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C

O,O-diisopropyl chlorothiophosphate
2524-06-3

O,O-diisopropyl chlorothiophosphate

Conditions
ConditionsYield
In chloroform for 3h;A 82%
B n/a
C 65%
...Expand
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

N-(2-mercaptophenyl) acetamide
1444-47-9

N-(2-mercaptophenyl) acetamide

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; potassium tert-butylate; 1,9-phenanthroline In N,N-dimethyl-formamide at 135℃; for 24h; Green chemistry;81%
With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; potassium tert-butylate In N,N-dimethyl-formamide at 135℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;81%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

thioacetic acid S-(2-acetylamino-phenyl)ester
1204-55-3

thioacetic acid S-(2-acetylamino-phenyl)ester

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;81%
2-iodochlorobenzene
615-41-8

2-iodochlorobenzene

N-(2-mercaptophenyl) acetamide
1444-47-9

N-(2-mercaptophenyl) acetamide

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; potassium tert-butylate; 1,9-phenanthroline In N,N-dimethyl-formamide at 135℃; for 24h; Green chemistry;80%
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With N-methoxy-1H-pyrrole-2-carboxamide; copper(ll) sulfate pentahydrate; potassium carbonate at 50℃; for 20h; Sealed tube;80%
With N-(benzyloxy)-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; sodium hydroxide at 90℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere; Green chemistry;70%
Multi-step reaction with 2 steps
1: N-(benzyloxy)-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; sodium hydroxide / 2 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
2: N-(benzyloxy)-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; sodium hydroxide / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
N-(2-mercaptophenyl) acetamide
1444-47-9

N-(2-mercaptophenyl) acetamide

chlorobenzene
108-90-7

chlorobenzene

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; potassium tert-butylate In N,N-dimethyl-formamide at 135℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;80%
10-(4-methylphenylsulfonyl)-10H-phenothiazine
58010-03-0

10-(4-methylphenylsulfonyl)-10H-phenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 8h; Inert atmosphere;77%
perchlorate of the radical cation of phenothiazine

perchlorate of the radical cation of phenothiazine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With zinc In acetonitrile for 0.0833333h; Ambient temperature;76%
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

S-(2-aminophenyl) 4-toluenethiosulfonate

S-(2-aminophenyl) 4-toluenethiosulfonate

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In Triethylene glycol dimethyl ether at 20℃; for 24h; Inert atmosphere;75%
1-(10H-phenothiazin-10-yl)propan-1-one
6622-75-9

1-(10H-phenothiazin-10-yl)propan-1-one

A

10H-phenothiazine
92-84-2

10H-phenothiazine

B

N-(α-propionyl)propionylphenothiazine
76331-04-9

N-(α-propionyl)propionylphenothiazine

Conditions
ConditionsYield
With n-butyl magnesium bromide In tetrahydrofuran for 20h; Ambient temperature;A n/a
B 74%
2-bromothiophenol
6320-02-1

2-bromothiophenol

2-iodophenylamine
615-43-0

2-iodophenylamine

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With N-methoxy-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; potassium hydroxide at 90℃; for 15h; Sealed tube;74%
(2-aminophenyl)-2’-bromophenyl sulfide
63107-77-7

(2-aminophenyl)-2’-bromophenyl sulfide

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With N-(benzyloxy)-1H-pyrrole-2-carboxamide; copper(II) acetate monohydrate; sodium hydroxide at 90℃; Sealed tube; Inert atmosphere; Green chemistry;72%
With ammonia; potassium amide
With copper(l) iodide; potassium carbonate; L-proline In ethyl methyl ether at 110℃; for 72h; Inert atmosphere;
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

N-(2-mercaptophenyl) acetamide
1444-47-9

N-(2-mercaptophenyl) acetamide

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; potassium tert-butylate; 1,9-phenanthroline In N,N-dimethyl-formamide at 135℃; for 24h; Green chemistry;72%
bromobenzene
108-86-1

bromobenzene

N-(2-mercaptophenyl) acetamide
1444-47-9

N-(2-mercaptophenyl) acetamide

10H-phenothiazine
92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; potassium tert-butylate In N,N-dimethyl-formamide at 135℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;72%
10H-phenothiazine
92-84-2

10H-phenothiazine

acetyl chloride
75-36-5

acetyl chloride

10-acetyl-10H-phenothiazine
1628-29-1

10-acetyl-10H-phenothiazine

Conditions
ConditionsYield
In toluene at 50℃; for 1h;100%
Stage #1: acetyl chloride With zinc(II) chloride In dichloromethane at 0℃; for 0.333333h;
Stage #2: 10H-phenothiazine In dichloromethane at 0 - 20℃; for 24h;		96%
In toluene for 0.166667h; Microwave irradiation;94.5%
10H-phenothiazine
92-84-2

10H-phenothiazine

allyl bromide
106-95-6

allyl bromide

10-allylphenothiazine
20962-92-9

10-allylphenothiazine

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In various solvent(s) for 2.5h; Ambient temperature;100%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 3h; Product distribution; Ambient temperature; other solvent;90%
87%
With sodium hydroxide; tetrabutylammomium bromide In toluene62%
With copper; sodium carbonate; benzene
10H-phenothiazine
92-84-2

10H-phenothiazine

3,7-dibromo-10H-phenothiazine
21667-32-3

3,7-dibromo-10H-phenothiazine

Conditions
ConditionsYield
With bromine; acetic acid at 20℃; for 16h; Inert atmosphere;100%
Stage #1: 10H-phenothiazine With bromine In acetic acid at 20℃; for 16h;
Stage #2: With water; potassium hydroxide		88%
With N-Bromosuccinimide In N,N-dimethyl-formamide for 10h; Cooling with ice;82%
10H-phenothiazine
92-84-2

10H-phenothiazine

phenothiazin-5-ium tetraiodide

phenothiazin-5-ium tetraiodide

Conditions
ConditionsYield
With iodine In dichloromethane at 20℃; for 4h;100%
With iodine In chloroform at 5℃; for 0.5h;87%
With iodine In chloroform80%
With iodine
10H-phenothiazine
92-84-2

10H-phenothiazine

1,2-Epoxy-3-bromopropane
3132-64-7

1,2-Epoxy-3-bromopropane

1-Chloro-3-phenothiazin-10-yl-propan-2-ol

1-Chloro-3-phenothiazin-10-yl-propan-2-ol

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide for 48h; Ambient temperature;100%
10H-phenothiazine
92-84-2

10H-phenothiazine

A

3,7-dibromo-10H-phenothiazine
21667-32-3

3,7-dibromo-10H-phenothiazine

B

3,7-dibromophenothiazinium bromide

3,7-dibromophenothiazinium bromide

Conditions
ConditionsYield
With bromine In acetic acid for 0.0166667h;A n/a
B 100%
10H-phenothiazine
92-84-2

10H-phenothiazine

3,7-dibromophenothiazinium bromide

3,7-dibromophenothiazinium bromide

Conditions
ConditionsYield
With bromine In acetic acid for 0.05h;100%
With bromine; acetic acid for 0.0166667h;100%
With bromine; acetic acid In diethyl ether for 0.0833333h;90.1%
With bromine In acetic acid at 20℃; for 0.0166667h;84%
With bromine In acetic acid for 0.0166667h;83%
10H-phenothiazine
92-84-2

10H-phenothiazine

phenothiazin-5-ium tetraiodide

phenothiazin-5-ium tetraiodide

Conditions
ConditionsYield
With iodine In chloroform Cooling with ice;100%
With iodine In chloroform at 0℃; for 16h;100%
With iodine In chloroform at 20℃; for 6h;93%
10H-phenothiazine
92-84-2

10H-phenothiazine

phenothiazin-5-ium tetraiodide

phenothiazin-5-ium tetraiodide

Conditions
ConditionsYield
With iodine In dichloromethane at 20℃; for 2h;100%
10H-phenothiazine
92-84-2

10H-phenothiazine

2-(5,5-diethoxypentyl)-2,3-dihydro-1H-isoindole-1,3-dione

2-(5,5-diethoxypentyl)-2,3-dihydro-1H-isoindole-1,3-dione

2-[5-(10H-phenothiazin-10-yl)pentyl]-2,3-dihydro-1H-isoindole-1,3-dione

2-[5-(10H-phenothiazin-10-yl)pentyl]-2,3-dihydro-1H-isoindole-1,3-dione

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
10H-phenothiazine
92-84-2

10H-phenothiazine

N-(4,4-diethoxybutyl)-2,2,2-trifluoroacetamide
84633-75-0

N-(4,4-diethoxybutyl)-2,2,2-trifluoroacetamide

N-[4-(10H-phenothiazin-10-yl)butyl]-2,2,2-trifluoroacetamide

N-[4-(10H-phenothiazin-10-yl)butyl]-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
10H-phenothiazine
92-84-2

10H-phenothiazine

tertiary butyl chloride
507-20-0

tertiary butyl chloride

3,7-di-tert-butyl-10H-phenothiazine
27075-55-4

3,7-di-tert-butyl-10H-phenothiazine

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 0.05h;99.5%
With aluminum (III) chloride In dichloromethane at 0℃; Inert atmosphere;85%
With aluminum (III) chloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;85%
Stage #1: 10H-phenothiazine; tertiary butyl chloride With aluminum (III) chloride In dichloromethane at 0℃;
Stage #2: With sodium acetate In water		81%
With aluminum (III) chloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;58%
ethyl bromide
74-96-4

ethyl bromide

10H-phenothiazine
92-84-2

10H-phenothiazine

10-ethyl-phenothiazine
1637-16-7

10-ethyl-phenothiazine

Conditions
ConditionsYield
Stage #1: 10H-phenothiazine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: ethyl bromide In tetrahydrofuran; mineral oil at 20℃; for 12.5h; Inert atmosphere;		99%
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 30 - 50℃; for 1h; Inert atmosphere;
Stage #2: ethyl bromide In N,N-dimethyl-formamide; mineral oil at 50℃; for 10h; Inert atmosphere;		98%
In ethanol at 110℃; for 24h;96.3%
10H-phenothiazine
92-84-2

10H-phenothiazine

methyl iodide
74-88-4

methyl iodide

N-methylphenothiazine
1207-72-3

N-methylphenothiazine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;99%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Cooling with ice;97%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Cooling with ice;97%
10H-phenothiazine
92-84-2

10H-phenothiazine

phenothiazine 5,5-dioxide
1209-66-1

phenothiazine 5,5-dioxide

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 60℃; for 1h;99%
With dihydrogen peroxide; acetic acid In dichloromethane at 50 - 100℃;90%
With dihydrogen peroxide; acetic acid In dichloromethane at 50 - 100℃;90%
10H-phenothiazine
92-84-2

10H-phenothiazine

2-nitro-2-propen-1-yl 2,2-dimethylpropanoate
78551-14-1

2-nitro-2-propen-1-yl 2,2-dimethylpropanoate

n-(2'-nitro-2'-propenyl)phenothiazine

n-(2'-nitro-2'-propenyl)phenothiazine

Conditions
ConditionsYield
In tetrahydrofuran 1.) -78 deg C, 25 deg C, 12 d.;99%
10H-phenothiazine
92-84-2

10H-phenothiazine

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

tert-butyl 2-(10-phenothiazinyl)acetate
295801-35-3

tert-butyl 2-(10-phenothiazinyl)acetate

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; butanone Alkylation;99%
With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; butanone
10H-phenothiazine
92-84-2

10H-phenothiazine

(Z)-β-bromostyrene
588-73-8

(Z)-β-bromostyrene

10-[(Z)-2-phenylethenyl]-10H-phenothiazine
108656-67-3

10-[(Z)-2-phenylethenyl]-10H-phenothiazine

Conditions
ConditionsYield
Stage #1: 10H-phenothiazine In 1,2-dimethoxyethane; toluene at 20℃; for 0.5h;
Stage #2: (Z)-β-bromostyrene With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane; toluene at 85℃; for 7h; Further stages.;		99%
10H-phenothiazine
92-84-2

10H-phenothiazine

[(E)-2-bromoethenyl]benzene
588-72-7

[(E)-2-bromoethenyl]benzene

10-[(E)-2-phenylethenyl]-10H-phenothiazine
108656-68-4

10-[(E)-2-phenylethenyl]-10H-phenothiazine

Conditions
ConditionsYield
Stage #1: 10H-phenothiazine In 1,2-dimethoxyethane; toluene at 20℃; for 0.5h;
Stage #2: [(E)-2-bromoethenyl]benzene With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane; toluene at 85℃; for 8h; Further stages.;		99%
10H-phenothiazine
92-84-2

10H-phenothiazine

mercaptoacetic acid 2-ethylhexyl ester
7659-86-1

mercaptoacetic acid 2-ethylhexyl ester

N-(2-Ethylhexyloxycarbonylmethylthiomethyl)-phenothiazine

N-(2-Ethylhexyloxycarbonylmethylthiomethyl)-phenothiazine

Conditions
ConditionsYield
With paraformaldehyde99%
10H-phenothiazine
92-84-2

10H-phenothiazine

3,4,5-trimethylphenol
527-54-8

3,4,5-trimethylphenol

C21H19NOS

C21H19NOS

Conditions
ConditionsYield
With oxygen In acetic acid at 150℃; for 24h; Sealed tube;99%
With (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride In toluene at 80℃; for 18h; Sealed tube;86%
10H-phenothiazine
92-84-2

10H-phenothiazine

triphenylsulfonium trifluoromethanesulfonate
66003-78-9

triphenylsulfonium trifluoromethanesulfonate

10-phenyl-10H-phenothiazine
7152-42-3

10-phenyl-10H-phenothiazine

Conditions
ConditionsYield
With potassium tert-butylate In toluene at 80℃; for 28h; Glovebox; Inert atmosphere; Sealed tube;99%
10H-phenothiazine
92-84-2

10H-phenothiazine

N-(3,3-dimethoxypropyl)acetamide
1262142-10-8

N-(3,3-dimethoxypropyl)acetamide

10-(N-acetyl-3-aminopropyl)-10H-phenothiazine

10-(N-acetyl-3-aminopropyl)-10H-phenothiazine

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere;99%
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃;
10H-phenothiazine
92-84-2

10H-phenothiazine

Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

methyl 4-[(10H-phenothiazine-10-yl)methyl]benzoate

methyl 4-[(10H-phenothiazine-10-yl)methyl]benzoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;99%
Stage #1: 10H-phenothiazine With lithium hexamethyldisilazane In N,N-dimethyl-formamide; toluene at 0℃; for 0.25h; Inert atmosphere;
Stage #2: Methyl 4-(bromomethyl)benzoate In N,N-dimethyl-formamide; toluene at 50℃; for 93h; Inert atmosphere;		70%
With potassium carbonate In acetonitrile for 36h; Reflux;62%
10H-phenothiazine
92-84-2

10H-phenothiazine

1,3,7-trichloro-10H-phenothiazine
60334-76-1

1,3,7-trichloro-10H-phenothiazine

Conditions
ConditionsYield
With phosphorus pentachloride In chloroform Reflux;99%
10H-phenothiazine
92-84-2

10H-phenothiazine

2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole
21510-43-0

2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole

C26H17N3OS

C26H17N3OS

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In toluene Buchwald-Hartwig Coupling; Reflux;98.5%
10H-phenothiazine
92-84-2

10H-phenothiazine

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With 3-Hydroxy-1-methylpiperidine; nickel diacetate; sodium hydride In tetrahydrofuran at 65℃; for 4h;98%
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol for 1h; Mechanism; Ambient temperature; kinetic isotope effect; desulfurization of other benzo- and dibenzothiophenes;68%
bei der Zinkstaub-Destillation;
10H-phenothiazine
92-84-2

10H-phenothiazine

acetic anhydride
108-24-7

acetic anhydride

10-acetyl-10H-phenothiazine
1628-29-1

10-acetyl-10H-phenothiazine

Conditions
ConditionsYield
With phosphoric acid at 60℃; for 0.166667h; Microwave irradiation; regioselective reaction;98%
at 120℃; for 4h;94%
In xylene
10H-phenothiazine
92-84-2

10H-phenothiazine

1-bromo-hexane
111-25-1

1-bromo-hexane

10-hexyl-10H-phenothiazine
73025-93-1

10-hexyl-10H-phenothiazine

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 66℃; for 3h;98%
With sodium hydride In tetrahydrofuran at 70℃; for 12h; Inert atmosphere;95%
Stage #1: 10H-phenothiazine With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;
Stage #2: 1-bromo-hexane In tetrahydrofuran at 66℃; for 4h;		94%
10H-phenothiazine
92-84-2

10H-phenothiazine

1-bromo-octane
111-83-1

1-bromo-octane

10-octyl-10H-phenothiazine
38076-72-1

10-octyl-10H-phenothiazine

Conditions
ConditionsYield
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h;
Stage #2: 1-bromo-octane In N,N-dimethyl-formamide at 20℃; for 6h;		98%
Stage #1: 10H-phenothiazine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.6h;
Stage #2: 1-bromo-octane at 20℃; Temperature; Solvent;		97%
With potassium hydroxide In dimethyl sulfoxide92%

Phenothiazine Chemical Properties

IUPAC Name: 10H-Phenothiazine
Synonyms of Phenothiazine (CAS NO.92-84-2): 10H-Phenothiazine ; 4-27-00-01214 (Beilstein Handbook Reference) ; AFI-Tiazin ; AI3-00038 ; Agrazine ; Antiverm ; BRN 0143237 ; Biverm ; CCRIS 5877 ; Caswell No. 652 ; Contaverm ; Dibenzo-1,4-thiazine ; Dibenzo-p-thiazine ; Dibenzoparathiazine ; Dibenzothiazine ; EINECS 202-196-5 ; ENT 38 ; EPA Pesticide Chemical Code 064501 ; Early bird wormer ; Feeno ; Fenothiazine ; Fenothiazine [Dutch] ; Fenotiazina ; Fenotiazina [INN-Spanish] ; Fenotiazina [Italian] ; Fenoverm ; Fentiazin ; HSDB 5279 ; Helmetina ; Lethelmin ; NSC 2037 ; Nemazene ; Nemazine ; Nexarbol ; Orimon ; Padophene ; Reconox ; Souframine ; Thiodifenylamine ; Thiodifenylamine [Dutch] ; Thiodiphenylamin ; Thiodiphenylamin [German] ; Thiodiphenylamine ; Tiodifenilamina ; Tiodifenilamina [Italian] ; UNII-GS9EX7QNU6 ; Vermitin ; Wurm-thional ; XL-50
CAS NO: 92-84-2
Classification Code: Agricultural Chemical ; Anti-Infective Agents ; Antiparasitic Agents ; Antiprotozoal Agents ; Drug / Therapeutic Agent ; Fungicide, bactericide, wood preservative ; Human Data ; Insecticide ; Mutation data ; Nematocide ; Reproductive Effect
Molecular Formula of Phenothiazine (CAS NO.92-84-2): C12H9NS
Molecular Weight: 199.2716
Molecular Structure:

Melting Point: 184 °C 
Polar Surface Area: 37.33 Å2
Index of Refraction: 1.674
Molar Refractivity: 60.69 cm3
Molar Volume: 161.5 cm3
Surface Tension: 52.5 dyne/cm
Density of Phenothiazine (CAS NO.92-84-2): 1.233 g/cm3
Flash Point: 178.2 °C
Enthalpy of Vaporization: 61.8 kJ/mol
Boiling Point: 371 °C at 760 mmHg
Vapour Pressure: 1.06E-05 mmHg at 25°C

Phenothiazine Uses

 Phenothiazine(CAS NO.92-84-2) is mainly used as the efficient inhibitor for acrylic acid , acrylic esters, and methacrylic acid ester.
There are three main therapeutic applications of the phenothiazine(CAS NO.92-84-2) drugs:
(1) they have an antiemetic effect (stop vomiting);
(2) they are used with anesthetics, potent analgesics (pain relievers), and sedatives to permit their use in smaller doses; 
(3) they are used most widely to relieve anx-iety and tension in various severe mental and emotional disorders.

Phenothiazine Production

The production of Phenothiazines (CAS NO.92-84-2) involves heating the appropriate meta-substituted diphenylamine with sulfur and an iodine catalyst to close the ring. Treatment with the strong base sodium amide gives the anion on the ring nitrogen, which then displaces the chlorine of the appropriate second reactant.

Phenothiazine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LDLo unreported 500mg/kg (500mg/kg)   Journal of the American Chemical Society. Vol. 66, Pg. 888, 1944.
cattle LD50 oral 500mg/kg (500mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1104, 1986.
child LDLo oral 425mg/kg/5D (425mg/kg) BEHAVIORAL: HEADACHE

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: NORMOCYTIC ANEMIA		 Lancet. Vol. 242, Pg. 86, 1942.
mouse LD50 intravenous 178mg/kg (178mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00586,
mouse LD50 oral 5gm/kg (5000mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Developments in Neuroscience Vol. 7, Pg. 45, 1980.
rabbit LD50 oral 4gm/kg (4000mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1104, 1986.

Phenothiazine Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Phenothiazine Safety Profile

Poison by intravenous route. Moderately toxic to humans by ingestion. Experimental reproductive effects. An insecticide. Large doses, i.e., heavy exposure, may cause hemolytic anemia and toxic degeneration of the liver. Can cause skin irritation and photosensitization. Dangerous; when heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of SOx and NOx.
Hazard Codes: Xi,Xn,N
Risk Statements:  36/37/38-43-51/53-36/38-40-20/21/22
36/37/38:  Irritating to eyes, respiratory system and skin 
43:  May cause sensitization by skin contact 
51/53:  Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
36/38:  Irritating to eyes and skin 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:  26-36-61-36/37/39-29-22
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
61:  Avoid release to the environment. Refer to special instructions safety data sheet 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
29:  Do not empty into drains 
22:  Do not breathe dust
WGK Germany:  1
F:  8-23: Photosensitive. Sensitive to air. 
HS Code:  29343090
Hazardous Substances Data: 92-84-2(Hazardous Substances Data)

Phenothiazine Standards and Recommendations

OSHA PEL: TWA 5 mg/m3 (skin)
ACGIH TLV: TWA 5 mg/m3 (skin)
NIOSH REL: (Phenothiazine) TWA 5 mg/m3 (skin)

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