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92-84-2

Basic Information
CAS No.: 92-84-2
Name: Phenothiazine
Article Data: 124
Cas Database
Molecular Structure:
Molecular Structure of 92-84-2 (Phenothiazine)
Formula: C12H9NS
Molecular Weight: 199.276
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;
EINECS: 202-196-5
Density: 1.233 g/cm3
Melting Point: 184 °C
Boiling Point: 371.003 °C at 760 mmHg
Flash Point: 178.176 °C
Solubility: water: 2 mg/L (25 °C)
Appearance: yellow or pale green powder
Hazard Symbols: IrritantXi,DangerousN,HarmfulXn
Risk Codes: 36/37/38-43-51/53-40-20/21/22
Safety: 26-61-36/37/39-29-22
Transport Information: N/A
PSA: 37.33000
LogP: 4.03280
Synthetic route

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

A

624-67-9

Propargylic aldehyde

B

92-84-2

10H-phenothiazine

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

10-acetyl-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
19210-66-3

10-vinyl-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%
583-55-1

1-Bromo-2-iodobenzene

137-07-5

2-amino-benzenethiol

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%
1628-29-1

10-acetyl-10H-phenothiazine

A

92-84-2

10H-phenothiazine

B

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%
92-39-7

2-chlorophenothiazine

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%
615-42-9

1,2-Diiodobenzene

1204-55-3

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

92-84-2

10H-phenothiazine

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

diphenylamine

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

92-84-2

10H-phenothiazine

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In acetonitrile at 20℃; for 0.5h;90%
72332-01-5

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

A

7335-06-0

1-ethylpyrrolidine

B

92-84-2

10H-phenothiazine

Conditions
ConditionsYield
at 200℃; for 0.5h; Yields of byproduct given;A n/a
B 89%
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Chemistry

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

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.

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.

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.

Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

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)

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)