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131707-23-8

Basic Information
CAS No.: 131707-23-8
Name: Arbidol hydrochloride
Article Data: 2
Cas Database
Molecular Structure:
Molecular Structure of 131707-23-8 (Arbidol hydrochloride)
Formula: C22H26BrClN2O3S
Molecular Weight: 513.883
Synonyms: 1H-Indole-3-carboxylicacid, 6-bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-, ethyl ester, monohydrochloride(9CI);Arbidol;Arbidolhydrochloride;
EINECS: 680-680-9
Density: N/A
Melting Point: 133-137?C
Boiling Point: 591.8 ºC at 760 mmHg
Flash Point: 311.7 ºC
Solubility: N/A
Appearance: White or off-white crystalline powder
Hazard Symbols: Xi
Risk Codes: 36/38
Safety: 26
Transport Information: N/A
PSA: 80.00000
LogP: 5.97900
Synthetic route
50-00-0

formaldehyd

124-40-3

dimethyl amine

131707-24-9

6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Stage #1: formaldehyd; dimethyl amine; 6-bromo-5-hydroxy-1-methyl-2-phenylthiomethylindole-3-carboxylic acid ethyl ester With aminosulfonic acid In water at 30 - 40℃; for 3h; Cooling with ice;
Stage #2: With hydrogenchloride In water; acetone at 60℃; pH=1;
85.6%
131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetone for 0.5h; Reflux;75%

C14H17NO4

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate; palladium diacetate; copper diacetate / N,N-dimethyl-formamide / 3 h / 80 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
3.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
4.1: sodium hydroxide / methanol / 2 h
4.2: 3 h
5.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
5.2: 60 °C / pH 1
View Scheme
20862-91-3

ethyl 5-acetyloxy-2-methyl-1H-indole-3-carboxylate

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
2.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
3.1: sodium hydroxide / methanol / 2 h
3.2: 3 h
4.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
4.2: 60 °C / pH 1
View Scheme
40945-79-7

1,2-dimethyl-5-acetoxy-1H-indole-3-carboxylic acid ethyl ester

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
2.1: sodium hydroxide / methanol / 2 h
2.2: 3 h
3.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
3.2: 60 °C / pH 1
View Scheme
Multi-step reaction with 4 steps
1.1: [RhCl2(p-cymene)]2; N-Bromosuccinimide / water; N,N-dimethyl acetamide / 24 h / 90 °C / Inert atmosphere
2.1: potassium hydroxide; methanol / 0.25 h / 20 °C
2.2: 4 h / 20 °C
3.1: acetic acid / water / 0.25 h / 0 °C
3.2: 4 h / 80 °C
4.1: hydrogenchloride / acetone / 0.5 h / Reflux
View Scheme
100-02-7

4-nitro-phenol

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: pyridine / acetone / 4 h / 20 °C / Reflux
2.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux
3.1: indium(III) bromide / dichloromethane / 3 h / Reflux
4.1: potassium carbonate; palladium diacetate; copper diacetate / N,N-dimethyl-formamide / 3 h / 80 °C
5.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
6.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
7.1: sodium hydroxide / methanol / 2 h
7.2: 3 h
8.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
8.2: 60 °C / pH 1
View Scheme
830-03-5

4-nitrophenol acetate

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: iron; ammonium chloride / ethanol; water / 2 h / Reflux
2.1: indium(III) bromide / dichloromethane / 3 h / Reflux
3.1: potassium carbonate; palladium diacetate; copper diacetate / N,N-dimethyl-formamide / 3 h / 80 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
5.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
6.1: sodium hydroxide / methanol / 2 h
6.2: 3 h
7.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
7.2: 60 °C / pH 1
View Scheme
13871-68-6

p-aminophenyl acetate

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: indium(III) bromide / dichloromethane / 3 h / Reflux
2.1: potassium carbonate; palladium diacetate; copper diacetate / N,N-dimethyl-formamide / 3 h / 80 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
4.1: dibenzoyl peroxide; bromine / chloroform / 3 h / Reflux
5.1: sodium hydroxide / methanol / 2 h
5.2: 3 h
6.1: aminosulfonic acid / water / 3 h / 30 - 40 °C / Cooling with ice
6.2: 60 °C / pH 1
View Scheme
15574-49-9

mecarbinate

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 4 h / Reflux
2.1: [RhCl2(p-cymene)]2; N-Bromosuccinimide / water; N,N-dimethyl acetamide / 24 h / 90 °C / Inert atmosphere
3.1: potassium hydroxide; methanol / 0.25 h / 20 °C
3.2: 4 h / 20 °C
4.1: acetic acid / water / 0.25 h / 0 °C
4.2: 4 h / 80 °C
5.1: hydrogenchloride / acetone / 0.5 h / Reflux
View Scheme
110543-98-1

5-acetoxy-6-bromo-2-bromomethyl-1-methylindole-3-carboxylic acid ethyl ester

131707-23-8

Arbidol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide; methanol / 0.25 h / 20 °C
1.2: 4 h / 20 °C
2.1: acetic acid / water / 0.25 h / 0 °C
2.2: 4 h / 80 °C
3.1: hydrogenchloride / acetone / 0.5 h / Reflux
View Scheme
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Chemistry

The Molecular Structure of Arbidol hydrochloride (CAS NO.131707-23-8):

Empirical Formula: C22H26BrClN2O3S
Molecular Weight: 513.8754 
Flash Point: 311.7 °C
Enthalpy of Vaporization: 91.52 kJ/mol
Boiling Point: 591.8 °C at 760 mmHg
Vapour Pressure: 1.34E-14 mmHg at 25°C 
Synonyms: 6-Bromo-4-[(dimethylamino)methyl]-5-hydroxy-1-methyl-2-[(phenylthio)methyl]-1H-indole-3-carboxylic acid ethyl ester monohydrochloride 

Uses

 Arbidol hydrochloride (CAS NO.131707-23-8) is a medicinal agent for treating viral infections.

Production

1,2-Dimethyl-5-hydroxyindole-3-acetic acid ethyl ester (I) is acetylated with acetic anhydride affording the O-acyl derivative (II) , which is brominated to the corresponding dibromide compound (III) . The reaction of (III) with thiophenol in KOH yields (IV) , which is then submitted to a conventional Mannich condensation with formaldehyde and dimethylamine in acetic acid, giving the free base of arbidol (V), which is treated with aqueous hydrochloric acid .


 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral > 3gm/kg (3000mg/kg)   Drugs of the Future. Vol. 17, Pg. 1079, 1992.
mouse LD50 oral 340mg/kg (340mg/kg)   Drugs of the Future. Vol. 17, Pg. 1079, 1992.
rat LD50 oral > 3gm/kg (3000mg/kg)   Drugs of the Future. Vol. 17, Pg. 1079, 1992.