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52-86-8

Basic Information
CAS No.: 52-86-8
Name: Haloperidol
Article Data: 29
Molecular Structure:
Molecular Structure of 52-86-8 (Haloperidol)
Formula: C21H23ClFNO2
Molecular Weight: 375.871
Synonyms: Butyrophenone,4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4'-fluoro- (6CI,8CI);4-(4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone;4-(4-Hydroxy-4'-chloro-4-phenylpiperidino)-4'-fluorobutyrophenone;Aloperidin;Bioperidolo;Brotopon;Dozic;Einalon S;Eukystol;Haldol;Haloperin;Keselan;McN-JR 1625;NSC 615296;Peluces;Serenace;Serenelfi;g-[4-(p-Chlorphenyl)-4-hydroxypiperidino]-p-fluorbutyrophenone;
EINECS: 200-155-6
Density: 1.239 g/cm3
Melting Point: 152 °C
Boiling Point: 529.034 °C at 760 mmHg
Flash Point: 273.75 °C
Solubility: 2.058mg/L(22.5 oC)
Appearance: white crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 60-61-25-36/37/38-43
Safety: 53-26-36/37/39-45
Transport Information: UN 2811 6.1/PG 3
PSA: 40.54000
LogP: 4.36350
Synthetic route
150717-69-4

4-(4-chlorophenyl)-1-<4-(4-nitrophenyl)-4-oxobutyl>-4-piperidinol

52-86-8

haloperidol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 160℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Anhydrous conditions;99%
With hydrogen fluoride; potassium oxalate; potassium carbonate; [2.2.2]cryptande65%
With hydrogen fluoride; potassium oxalate; potassium carbonate; [2.2.2]cryptande In dimethyl sulfoxide at 160℃; for 0.333333h;60%
39512-49-7

4-(4-chlorophenyl)-4-hydroxypiperidine

3874-54-2

4-(4-fluorophenyl)-4-oxo-n-butyl chloride

52-86-8

haloperidol

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 75℃; for 24h; Temperature;88%
With potassium iodide In toluene for 45h; Reflux;85%
With potassium iodide In toluene at 130℃; for 45h; Sealed tube;79%
56660-99-2

4-<4-(4-chlorophenyl)-4-hydroxypiperidino>-1,1-ethylenedioxy-1-(4-fluorophenyl)butane

52-86-8

haloperidol

Conditions
ConditionsYield
With hydrogenchloride In methanol for 6h; Heating;65%
With hydrogenchloride In methanol for 2h; Heating;65%
132993-23-8

4-fluorophenyl trifluoromethanesulfonate

4-(4-chlorophenyl)-1-(4-hydroxybutyl)piperidin-4-ol

52-86-8

haloperidol

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)nickel (0); acetone; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 130℃; for 20h; Inert atmosphere;37%
59995-68-5

Chlorohaloperidol

52-86-8

haloperidol

Conditions
ConditionsYield
With hydrogen fluoride; tetra(n-butyl)ammonium hydroxide
39512-49-7

4-(4-chlorophenyl)-4-hydroxypiperidine

52-86-8

haloperidol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / acetic acid; NaCNBH3 / methanol / 30 h / 20 °C
2: 65 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: K2CO3, KI / dimethylformamide / 17.5 h / 100 °C
2: 65 percent / conc. HCl / methanol / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium iodide / toluene / 48 h / Reflux; Inert atmosphere
2: bis(1,5-cyclooctadiene)nickel (0); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; acetone; 2,2,6,6-tetramethyl-piperidine / toluene / 20 h / 130 °C / Inert atmosphere
View Scheme
39560-31-1

methyl 3-(4-fluorobenzoyl)-propionate

52-86-8

haloperidol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / p-TsOH / benzene / 20 h / Heating
2: 93 percent / DIBAL-H / CH2Cl2; tetrahydrofuran / 1 h / -78 °C
3: 78 percent / acetic acid; NaCNBH3 / methanol / 30 h / 20 °C
4: 65 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
847025-06-3

3-[2-(4-fluorophenyl)-[1,3]dioxolan-2-yl]propionaldehyde

52-86-8

haloperidol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / acetic acid; NaCNBH3 / methanol / 30 h / 20 °C
2: 65 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
847025-05-2

3-[2-(4-fluorophenyl)-[1,3]dioxolan-2-yl]propionic acid methyl ester

52-86-8

haloperidol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / DIBAL-H / CH2Cl2; tetrahydrofuran / 1 h / -78 °C
2: 78 percent / acetic acid; NaCNBH3 / methanol / 30 h / 20 °C
3: 65 percent / conc. HCl / methanol / 2 h / Heating
View Scheme
57189-90-9

(4-aminophenyl)(cyclopropyl)methanone

52-86-8

haloperidol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h
2: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C
3: 31 percent / KI / toluene / 100 - 110 °C
4: 60 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / 0.33 h / 160 °C
View Scheme
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Specification

The Haloperidol, with the CAS registry number 52-86-8 and EINECS registry number 200-155-6, has the systematic name of 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one. It is a kind of white crystalline powder, and belongs to the following product categories: Organics; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Dopamine receptor; Dopamine. The molecular formula of this chemical is C21H23ClFNO2.

The physical properties of Haloperidol are as following: (1)ACD/LogP: 3.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.232; (4)ACD/LogD (pH 7.4): 2.931; (5)ACD/BCF (pH 5.5): 1.261; (6)ACD/BCF (pH 7.4): 63.047; (7)ACD/KOC (pH 5.5): 7.871; (8)ACD/KOC (pH 7.4): 393.605; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 40.54 Å2; (13)Index of Refraction: 1.581; (14)Molar Refractivity: 101.012 cm3; (15)Molar Volume: 303.279 cm3; (16)Polarizability: 40.044×10-24cm3; (17)Surface Tension: 47.906 dyne/cm; (18)Density: 1.239 g/cm3; (19)Flash Point: 273.75 °C; (20)Enthalpy of Vaporization: 84.63 kJ/mol; (21)Boiling Point: 529.034 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C. 

Preparation of Haloperidol: It can be prepared by the condensation of 4-chlorophenyl-4-hydroxypiperidine with γ-chloro-p-Fluorophenyl methyl ethyl ketone. And the intermediate γ-chloro-fluoro-butanone can be prepared by fluorobenzene, γ-butyrolactone and thionyl chloride.

Uses of Haloperidol: It is an effective agent in treatment of symptoms associated with schizophrenia, and it is also used in the control of the symptoms of: (1)Acute psychosis; (2)Acute manic phases until the concomitantly given first-line drugs; (3)Otherwise uncontrollable severe behavioral disorders in children and adolescents; (4)Agitation and confusion associated with cerebral sclerosis; (5)Adjunctive treatment of alcohol and opioid withdrawal; (6)Treatment of nausea, vomiting, and delirium in palliative care; (7)Treatment of neurological disorders such as tic disorders; (8)Tourette syndrome, and chorea; (9)Treatment of severe nausea/emesi; (10)Adjunctive treatment of severe chronic pain, always together with analgesics; (11)Therapeutic trial in personality disorders; (12)Also used in the treatment of intractable hiccups.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also toxic if swallowed. And it may cause sensitization by skin contact. What's more, it may impair fertility and harm to the unborn child. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Avoid exposure - obtain special instruction before use.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1C(=O)CCCN2CCC(CC2)(c3ccc(cc3)Cl)O)F
(2)InChI: InChI=1/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
(3)InChIKey: LNEPOXFFQSENCJ-UHFFFAOYAL

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous > 2500ug/kg (2.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
child TDLo oral 72ug/kg (0.072mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
child TDLo unreported 375ug/kg/3D (0.375mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Lancet. Vol. 2, Pg. 479, 1980.
dog LD50 intravenous 18mg/kg (18mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
dog LD50 oral 90mg/kg (90mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
dog LD50 subcutaneous > 80mg/kg (80mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
human TDLo oral 71ug/kg (0.071mg/kg) BEHAVIORAL: EXCITEMENT Journal of Clinical Pyschopharmacology. Vol. 5, Pg. 120, 1985.
human TDLo unreported 9800ug/kg/28D (9.8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 911, 1982.
infant TDLo unreported 280ug/kg (0.28mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION

BEHAVIORAL: IRRITABILITY
Acta Paediatrica. Vol. 82, Pg. 877, 1993.
mammal (species unspecified) LD50 oral 80mg/kg (80mg/kg)   Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 320, Pg. 242, 1991.
mammal (species unspecified) LD50 unreported 80mg/kg (80mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(7), Pg. 27, 1990.
man TDLo multiple routes 343ug/kg (0.343mg/kg) BEHAVIORAL: TREMOR Southern Medical Journal. Vol. 76, Pg. 546, 1983.
man TDLo multiple routes 1mg/kg/1D-I (1mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Journal of Clinical Pyschopharmacology. Vol. 3, Pg. 338, 1983.
man TDLo oral 480ug/kg/6D-I (0.48mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY
American Journal of Psychiatry. Vol. 142, Pg. 389, 1985.
man TDLo oral 9mg/kg/30W-I (9mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Biological Psychiatry. Vol. 22, Pg. 111, 1987.
man TDLo unreported 500ug/kg/5D-I (0.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) JAMA, Journal of the American Medical Association. Vol. 250, Pg. 485, 1983.
monkey LD50 subcutaneous > 1250ug/kg (1.25mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Bollettino Chimico Farmaceutico. Vol. 111, Pg. 293, 1972.
mouse LD50 intravenous 13mg/kg (13mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY
Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961.
mouse LD50 oral 71mg/kg (71mg/kg)   Farmaco, Edizione Scientifica. Vol. 31, Pg. 442, 1976.
mouse LD50 subcutaneous 41mg/kg (41mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 1, Pg. 74, 1967.
mouse LD50 unreported 18mg/kg (18mg/kg)   Clinical Pharmacology and Therapeutics Vol. 3, Pg. 432, 1962.
rabbit LD50 intravenous 8mg/kg (8mg/kg)   Clinical Pharmacology and Therapeutics Vol. 8, Pg. 770, 1967.
rat LD50 intraperitoneal 27mg/kg (27mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 190, 1972.
rat LD50 intravenous 15mg/kg (15mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
rat LD50 oral 128mg/kg (128mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
rat LD50 subcutaneous 60mg/kg (60mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 45, 1974.
women TDLo intravenous 18300ug/kg/7D (18.3mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Annals of Pharmacotherpy. Vol. 33, Pg. 1046, 1999.
women TDLo oral 100ug/kg/10D- (0.1mg/kg) BLOOD: AGRANULOCYTOSIS Journal of the American Geriatrics Society. Vol. 35, Pg. 248, 1987.