CAS No.58-39-9,PERPHENAZINE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	58-39-9
Name:	PERPHENAZINE
Article Data:	11

Formula:	C₂₁H₂₆ClN₃OS
Molecular Weight:	403.976
Synonyms:	1-Piperazineethanol,4-[3-(2-chlorophenothiazin-10-yl)propyl]- (8CI);1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine;2-Chloro-10-3-[1-(2-hydroxyethyl)-4-piperazinyl] propyl phenothiazine;2-Chloro-10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazine;Chloriprozine;Chlorperphenazine;Decentan;Emesinal;Etaperazin;Etaperazine;Ethaperazine;Fentazin;Fentazin syrup;Fentazine duolets;Mutabom;NSC 150866;PZC;Perfenazine;Perfenil;Perphenan;Perphenazin;Sch 3940;Thilatazin;Tranquisan;Trifaron;Trilafon;Trilifan;Triphenot;g-[4-(b-Hydroxyethyl)piperazin-1-yl]propyl-2-chlorophenothiazine;4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol;
EINECS:	200-381-5
Density:	1.253 g/cm³
Melting Point:	35339ºC
Boiling Point:	580.4 °C at 760 mmHg
Flash Point:	304.8 °C
Solubility:	28.28mg/L(24 oC)
Appearance:	Off-white to pale yellow solid
Hazard Symbols:	Xn
Risk Codes:	22-43
Safety:	28-36/37/39-45
PSA:	55.25000
LogP:	3.88350

Synthetic route

: 103-76-4
1-(2-hydroxyethyl)piperazine

: 2765-59-5
2-chloro-10-(3-chloropropyl)-10H-phenothiazine

: 58-39-9
perphenazine

: 40323-85-1
N-Demethyl prochlorperazine

: 540-51-2
2-bromoethanol

: 58-39-9
perphenazine

Conditions

Conditions	Yield
With potassium carbonate; toluene

: 92-39-7
2-chlorophenothiazine

: 58-39-9
perphenazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaNH2; liquid NH3 View Scheme

: 2765-59-5
2-chloro-10-(3-chloropropyl)-10H-phenothiazine

: 58-39-9
perphenazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI; butanone 2: K2CO3; toluene View Scheme

: 75-75-2
methanesulfonic acid

: 503537-30-2
perphenazine N-Boc-4-aminobutyrate

A: 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethyl 4-aminobutyryl ester trimesylate

B: 58-39-9
perphenazine

Conditions

Conditions	Yield
In acetonitrile at 0 - 40℃; for 6h; Product distribution / selectivity;

...Expand

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 58-39-9
perphenazine

A: 504-07-4
5,6-dhydrouracil

B: 503537-30-2
perphenazine N-Boc-4-aminobutyrate

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-4-aminobutanoic acid; perphenazine With dmap In dichloromethane at 0 - 5℃; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Product distribution / selectivity;	A n/a B 98%

...Expand

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 58-39-9
perphenazine

: 503537-30-2
perphenazine N-Boc-4-aminobutyrate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Product distribution / selectivity; Industry scale; Inert atmosphere;	98%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 4h; Product distribution / selectivity;	97%

: 58-39-9
perphenazine

: 10078-25-8
perphenazine sulfoxide

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water for 2h;	95%

: 58-39-9
perphenazine

: 10272-07-8
3,5-Dimethoxyaniline

: 2-(4-(3-(2-((3,5-dimethoxyphenyl)amino)-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethan-1-ol

Conditions

Conditions	Yield
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;	92%

: 57294-38-9
N-(tert-butoxycarbonyl)-4-aminobutanoic acid

: 58-39-9
perphenazine

A: 2-(4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl pivalate

B: 503537-30-2
perphenazine N-Boc-4-aminobutyrate

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-4-aminobutanoic acid; pivaloyl chloride With triethylamine In tetrahydrofuran Stage #2: perphenazine In tetrahydrofuran at 50℃; for 16h; Product distribution / selectivity;	A n/a B 90%

...Expand

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Specification

The IUPAC name of Perphenazine is 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol. With the CAS registry number 58-39-9, it is also named as 1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-. The product's categories are Organics; Antagonists Forensic and Veterinary Standards; Chemical Structure; Dopaminergics; Drugs & Metabolites; Neat Compounds Drugs of Abuse; Neurotransmitters; Others. Besides, it is white crystalline powder, which should be stored at 2-8 °C. In addition, its molecular formula is C₂₁H₂₆ClN₃OS and molecular weight is 403.97.

The other characteristics of this product can be summarized as: (1)EINECS: 200-381-5; (2)ACD/LogP: 4.34; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.88; (5)ACD/LogD (pH 7.4): 4.21; (6)ACD/BCF (pH 5.5): 40.74; (7)ACD/BCF (pH 7.4): 863.6; (8)ACD/KOC (pH 5.5): 190.38; (9)ACD/KOC (pH 7.4): 4036; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 7; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 114.22 cm³; (15)Molar Volume: 322.3 cm³; (16)Surface Tension: 50.9 dyne/cm; (17)Density: 1.253 g/cm³; (18)Flash Point: 304.8 °C; (19)Melting Point: 97 °C; (20)Water Solubility: 28.3 mg/L at 24 °C; (21)Enthalpy of Vaporization: 91.32 kJ/mol; (22)Boiling Point: 580.4 °C at 760 mmHg; (23)Vapour Pressure: 2.6E-14 mmHg at 25 °C.

Production of Perphenazine: frist, you can use N-(2-Hydroxyethyl) piperazine to produce 1-(3-Chloropropyl)-4-(2-hydroxyethyl) piperazine by condensation with Trimethylene bromochloride. And then please use it to produce crude product by condensation with 2-Chlorophenothiazine. Afterwards, you will obtain this chemical after recrystallize it by the use of Ethyl acetate.

Uses of Perphenazine: this chemical is a typical antipsychotic drug to treat psychosis (e.g. in schizophrenics) and the manic phases of bipolar disorder. It also can be used to treat agitated depression (together with an antidepressant) in low doses. Furthermore, it can be used to produce 2-{4-[3-(2-Chloro-5-oxo-5H-5l4-phenothiazin-10-yl)-propyl]-πperazin-1-yl}-ethanol.

This reaction needs NaNO₂, HCl and H₂O for 2 hours. The yield is 95 %.

When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. And it also may cause sensitization by skin contact. You should wear suitable protective clothing, gloves and eye/face protection. After contact with skin, please wash immediately with plenty of soap-suds. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

People can use the following data to convert to the molecule structure.
(1)SMILES: Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(CCO)CC4
(2)InChI: InChI=1/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
(3)InChIKey: RGCVKNLCSQQDEP-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
(5)Std. InChIKey: RGCVKNLCSQQDEP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	32mg/kg (32mg/kg)		Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
cat	LD50	intravenous	35mg/kg (35mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
cat	LD50	subcutaneous	> 2500ug/kg (2.5mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
cat	LDLo	oral	1gm/kg (1000mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
dog	LD50	intravenous	51mg/kg (51mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: REGIDITY GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
dog	LD50	subcutaneous	> 20mg/kg (20mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
human	TDLo	intramuscular	71428ng/kg (0.071428mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	British Medical Journal. Vol. 3, Pg. 867, 1967.
monkey	LD50	subcutaneous	> 510ug/kg (0.51mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse	LD50	intraperitoneal	64mg/kg (64mg/kg)		Journal of Pharmaceutical Sciences. Vol. 59, Pg. 976, 1970.
mouse	LD50	intravenous	19mg/kg (19mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: REGIDITY	Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse	LD50	oral	120mg/kg (120mg/kg)		"Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 185, 1973.
mouse	LD50	subcutaneous	> 80mg/kg (80mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
pigeon	LD50	intramuscular	250mg/kg (250mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
pigeon	LD50	intravenous	32mg/kg (32mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960.
rat	LD50	intraperitoneal	146mg/kg (146mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 917, 1974.
rat	LD50	intravenous	34mg/kg (34mg/kg)		Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971.
rat	LD50	oral	318mg/kg (318mg/kg)		Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
rat	LD50	subcutaneous	> 80mg/kg (80mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.