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92-84-2 Usage

Uses

  • Phenothiazine is a relatively widely used anthelmintic reagent with excellent efficacy in treating the Haemonchus contortus of cattle, horse and sheep, nodular worm, Bunostomum and Plasmodium chabaudi.
  • Phenothiazine is the intermediates of fine chemicals such as dyes and drugs with itself being a auxiliary material for synthetic material (the anti-polymerization reagent for production of vinylon), fruit pesticides and veterinary anthelmintic.
  • It is mainly used as the polymerization inhibitor for acrylic acid, acrylic esters, and methacrylic aicd as well as ester monomer.

Reactivity Profile

Phenothiazine is slowly decomposed by sunlight. . Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Chemical Properties

yellow or pale green powder

Fire Hazard

Flash point data for Phenothiazine are not available, but Phenothiazine is probably combustible.

Uses

A rigid, tricyclic thiazine useful as an electron donor.

Uses

A key component of antipsychotic and antihistaminic drugs.

Uses

Insecticide; manufacture of pharmaceuticals.

Brand name

Nemazine (Parke-Davis).

Purification Methods

Crystallise it from *benzene, toluene, hexane or Me2CO (charcoal) after boiling for 10minutes under reflux. Filter the crystals off and dry them in an oven at 100o, then in a vacuum desiccator over paraffin chips. Also recrystallise it twice from water and dry it in an oven at 100o for 8-10hours. It sublimes at 130o/1mm and has UV with at 253nm in heptane. [Beilstein

Air & Water Reactions

Insoluble in water.

Chemical Properties

It is clean gray-green powder with the melting point of 185.5 ℃, boiling point of 371 ℃, 290 ℃ (5.33kPa). It is insoluble in petroleum ether, chloroform and water, and soluble in ether and hot acetic acid. It will be oxidized upon exposure to light in the air.

description

Phenothiazine is a class of agents exhibiting antiemetic, antipsychotic, antihistaminic, and anticholinergic activities. Phenothiazines antagonize the dopamine D2-receptor in the chemoreceptor trigger zone (CTZ) of the brain, potentially preventing chemotherapy-induced emesis. In addition, these agents have peripherally or centrally antagonistic activity against alpha adrenergic, serotonergic, histaminic, and muscarinic receptors.
Phenothiazines are used to treat serious mental and emotional disorders, including schizophrenia and other psychotic disorders. Some are used also to control agitation in certain patients, severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients. Chlorpromazine is used also in the treatment of certain types of porphyria, and with other medicines in the treatment of tetanus. Phenothiazines may also be used for other conditions as determined by your doctor.

General Description

Light green to steel-blue powder. Acquires a greenish-brown tint under exposure to sunlight.

Synthesis

22 g of diphenylamine, 8.2 g of sulfur, and 3.2 gms. of anhydrous aluminum chloride are melted together. The reaction sets 140-150° C with the rapid evolution of hydrogen sulfide; by lowerg the temperature, a few degrees the reaction can be slackened. Wen the reaction has moderated, the temperature is raised to 160° C for a time. The melt, when cool, is ground up and extracted, first with water and then with dilute alcohol. The residue consists of almost pure phenothiazine. It can be recrystallised from alcohol. Yield 93%, yellowish leaflets; m.p. 180° C.
Preparation of phenothiazine
Systematic organic chemistry, by W. M. Cumming, 325-326, 1937.

Definition

ChEBI: The 10H-tautomer of phenothiazine.

Uses

Employed in the preparation of carbazoles and piperazines,1 and charge-transfer semiconducting complexes.2

side effects

For more than a decade, phenothiazine drugs have been used to treat a variety of disorders and have proved particularly effective in the treatment of schizophrenia. Clinical experience indicates that initial extremely high dosages are necessary to effect improvement of patients with schizophrenic illnesses.
During 1964, several sequelae have been reported following prolonged high dosage of these drugs. These recent reports refer to side effects which are apparently permanent, in contrast to earlier communications of transient deleterious effects. For example, it has been known for several years that extrapyramidal disorders occur frequently in patients taking phenothiazines; however, a reduction in dosage or cessation of medication appeared to produce a return to the normal state.
Phenothiazines may cause unwanted, unattractive, and uncontrolled face or body movements that may not go away when you stop taking the medicine. They may also cause other serious unwanted effects. You and your doctor should talk about the good this medicine will do as well as the risks of using it. Also, your doctor should look for early signs of these effects at regular visits. Your doctor may be able to stop or decrease some unwanted effects, if they do occur, by changing your dose or by making other changes in your treatment.
These medicines are available only with your doctor's prescription.
Levoprome(R) (methotrimeprazine) is no longer available in the United States. At the end of May 1998, Immunex Corporation stopped marketing it.
Once a medicine has been approved for marketing for a certain use, experience may show that it also is useful for other medical problems. Although these uses are not included in product labeling, phenothiazines are used in certain patients with the following medical conditions:
  • Chronic neurogenic pain (certain continuing pain conditions)
  • Huntington's chorea (hereditary movement disorder)
  • Migraine headaches

92-84-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1525707)  Phenothiazine  United States Pharmacopeia (USP) Reference Standard 92-84-2 1525707-500MG 4,662.45CNY Detail
Vetec (V900773)  Phenothiazine  Vetec reagent grade, 98% 92-84-2 V900773-250G 168.48CNY Detail
Aldrich (P14831)  Phenothiazine  ≥98% 92-84-2 P14831-1KG 936.00CNY Detail
Aldrich (P14831)  Phenothiazine  ≥98% 92-84-2 P14831-500G 552.24CNY Detail
Aldrich (P14831)  Phenothiazine  ≥98% 92-84-2 P14831-25G 193.05CNY Detail
Sigma-Aldrich (88580)  Phenothiazine  purum, ≥98.0% (GC) 92-84-2 88580-1KG 936.00CNY Detail
Sigma-Aldrich (88580)  Phenothiazine  purum, ≥98.0% (GC) 92-84-2 88580-250G 547.56CNY Detail
Sigma-Aldrich (88580)  Phenothiazine  purum, ≥98.0% (GC) 92-84-2 88580-50G 296.01CNY Detail
Sigma-Aldrich (46624)  Phenothiazine  VETRANAL, analytical standard 92-84-2 46624-250MG 360.36CNY Detail
Alfa Aesar (A12517)  Phenothiazine, 98+%    92-84-2 5000g 3351.0CNY Detail
Alfa Aesar (A12517)  Phenothiazine, 98+%    92-84-2 500g 389.0CNY Detail
Alfa Aesar (A12517)  Phenothiazine, 98+%    92-84-2 250g 204.0CNY Detail

92-84-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 10H-phenothiazine

1.2 Other means of identification

Product number -
Other names Thiodiphenylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Process regulators,Processing aids, not otherwise listed
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:92-84-2 SDS

92-84-2Synthetic 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%
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%

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