Product Name

  • Name

    Clomethiazole

  • EINECS 208-565-7
  • CAS No. 533-45-9
  • Article Data19
  • CAS DataBase
  • Density 1.219 g/cm3
  • Solubility
  • Melting Point 127-128 °C
  • Formula C6H8ClNS
  • Boiling Point 245.774 °C at 760 mmHg
  • Molecular Weight 161.655
  • Flash Point 102.441 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 533-45-9 (Clomethiazole)
  • Hazard Symbols
  • Synonyms 4-Methyl-5-(b-chloroethyl)thiazole;5-(2-Chloroethyl)-4-methylthiazole;5-(b-Chloroethyl)-4-methylthiazole;Chlorethiazol;Chlorethiazole;Chlormethiazol;Chlormethiazole;Clomethiazole;Clomethiazolum;Distraneurin;Emineurina;Somnevrin;
  • PSA 41.13000
  • LogP 3.03480

Synthetic route

5-hydroxyethyl-4-methylthiazole
137-00-8

5-hydroxyethyl-4-methylthiazole

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
With thionyl chloride for 3h; Reflux;98%
With thionyl chloride for 2h; Heating;96%
With phosphorus pentachloride In dichloromethane for 3h; Heating;95%
5-(2-chloro-ethyl)-4-methyl-3H-thiazole-2-thione

5-(2-chloro-ethyl)-4-methyl-3H-thiazole-2-thione

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide
5-(2-ethoxyethyl)-4-methylthiazole
853261-35-5

5-(2-ethoxyethyl)-4-methylthiazole

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
With hydrogenchloride
5-ethoxy-3-chloro-pentan-2-one
663179-27-9

5-ethoxy-3-chloro-pentan-2-one

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: concentrated aqueous HCl
View Scheme
2-(2-ethoxy-ethyl)-2-chloro-acetoacetic acid ethyl ester
663179-24-6

2-(2-ethoxy-ethyl)-2-chloro-acetoacetic acid ethyl ester

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: glacial acetic acid; H2SO4
3: concentrated aqueous HCl
View Scheme
3-chloro-3-acetylpropanol
13045-13-1

3-chloro-3-acetylpropanol

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol
2: concentrated aqueous HCl
View Scheme
3, 5-dichloro-2-pentanone
58371-98-5

3, 5-dichloro-2-pentanone

chlormethiazole
533-45-9

chlormethiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / anschliessend Behandeln mit H2O
2: H2O2; concentrated aqueous HCl
View Scheme
sodium cyanide
773837-37-9

sodium cyanide

chlormethiazole
533-45-9

chlormethiazole

3-(4-methyl-thiazol-5-yl)propionitrile
6469-34-7

3-(4-methyl-thiazol-5-yl)propionitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 80℃; for 8h;98%
chlormethiazole
533-45-9

chlormethiazole

dimethyl sulfate
77-78-1

dimethyl sulfate

5-(β-Chloroethyl)-3,4-dimethylthiazolium methyl sulfate
78919-46-7

5-(β-Chloroethyl)-3,4-dimethylthiazolium methyl sulfate

Conditions
ConditionsYield
In acetone at 20℃; for 24h;85%
chlormethiazole
533-45-9

chlormethiazole

potassium phtalimide
1074-82-4

potassium phtalimide

4-methyl-5-(β-phthalimidoethyl)thiazole
36956-91-9

4-methyl-5-(β-phthalimidoethyl)thiazole

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100 - 105℃; for 2h;67%
In N,N-dimethyl-formamide (heating);
chlormethiazole
533-45-9

chlormethiazole

5-(2-chloroethyl)-2-iodo-4-methylthiazole
330436-68-5

5-(2-chloroethyl)-2-iodo-4-methylthiazole

Conditions
ConditionsYield
Stage #1: chlormethiazole With methyllithium In diethyl ether at -40℃;
Stage #2: With iodine In diethyl ether at -40 - 20℃; Further stages.;		63%
chlormethiazole
533-45-9

chlormethiazole

potassium cyanide
151-50-8

potassium cyanide

3-(4-methyl-thiazol-5-yl)propionitrile
6469-34-7

3-(4-methyl-thiazol-5-yl)propionitrile

Conditions
ConditionsYield
In ethanol; water at 70℃; for 24h;60%
chlormethiazole
533-45-9

chlormethiazole

1-(benzo[b]thiophen-4-yl)piperazine hydrochloride

1-(benzo[b]thiophen-4-yl)piperazine hydrochloride

5-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-4-methylthiazole hydrochloride

5-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-4-methylthiazole hydrochloride

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile Reflux;39%
chlormethiazole
533-45-9

chlormethiazole

N-(3-Chlorobenzyl)-1H-indazole-6-carboxamide
1002110-68-0

N-(3-Chlorobenzyl)-1H-indazole-6-carboxamide

N-(3-Chlorobenzyl)-2-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]-2H-indazole-6-carboxamide
1002109-98-9

N-(3-Chlorobenzyl)-2-[2-(4-methyl-1,3-thiazol-5-yl)ethyl]-2H-indazole-6-carboxamide

Conditions
ConditionsYield
With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;8%
chlormethiazole
533-45-9

chlormethiazole

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

bis-(2-hydroxy-ethyl)-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine
99977-12-5

bis-(2-hydroxy-ethyl)-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine

Conditions
ConditionsYield
With ethanol
chlormethiazole
533-45-9

chlormethiazole

thiourea
17356-08-0

thiourea

S-[2-(4-methyl-thiazol-5-yl)-ethyl]-isothiourea

S-[2-(4-methyl-thiazol-5-yl)-ethyl]-isothiourea

chlormethiazole
533-45-9

chlormethiazole

trimethylamine
75-50-3

trimethylamine

trimethyl-[2-(4-methyl-thiazol-5-yl)-ethyl]-ammonium; chloride

trimethyl-[2-(4-methyl-thiazol-5-yl)-ethyl]-ammonium; chloride

Conditions
ConditionsYield
With benzene
piperidine
110-89-4

piperidine

chlormethiazole
533-45-9

chlormethiazole

1-[2-(4-methyl-thiazol-5-yl)-ethyl]-piperidine
36956-90-8

1-[2-(4-methyl-thiazol-5-yl)-ethyl]-piperidine

Conditions
ConditionsYield
In butanone Heating;
morpholine
110-91-8

morpholine

chlormethiazole
533-45-9

chlormethiazole

4-[2-(4-methyl-thiazol-5-yl)-ethyl]-morpholine
36958-88-0

4-[2-(4-methyl-thiazol-5-yl)-ethyl]-morpholine

Conditions
ConditionsYield
In butanone (heating);
chlormethiazole
533-45-9

chlormethiazole

methylthiol
74-93-1

methylthiol

4-methyl-5-(2-methylsulfanyl-ethyl)-thiazole
33121-10-7

4-methyl-5-(2-methylsulfanyl-ethyl)-thiazole

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide Ambient temperature;
chlormethiazole
533-45-9

chlormethiazole

diethylamine
109-89-7

diethylamine

diethyl-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine
95164-46-8

diethyl-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine

Conditions
ConditionsYield
In nitrobenzene (heating);
chlormethiazole
533-45-9

chlormethiazole

4-methyl-5-vinylthiazole
1759-28-0

4-methyl-5-vinylthiazole

Conditions
ConditionsYield
With sodium ethanolate (heating);
chlormethiazole
533-45-9

chlormethiazole

1,3-Diiodopropane
627-31-6

1,3-Diiodopropane

C15H22Cl2N2S2(2+)*2I(1-)
76800-93-6

C15H22Cl2N2S2(2+)*2I(1-)

Conditions
ConditionsYield
In acetone Ambient temperature;
chlormethiazole
533-45-9

chlormethiazole

clomethiazol-I2
107814-79-9

clomethiazol-I2

Conditions
ConditionsYield
With iodine In tetrachloromethane at 20℃; Thermodynamic data; ΔH0, ΔS0, ΔG0;
chlormethiazole
533-45-9

chlormethiazole

5-(2-chloroethyl)-2-hex-1-ynyl-4-methylthiazole
330436-76-5

5-(2-chloroethyl)-2-hex-1-ynyl-4-methylthiazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: MeLi / diethyl ether / -40 °C
1.2: 63 percent / I2 / diethyl ether / -40 - 20 °C
2.1: 84 percent / Et3N; Pd(PPh3)2Cl2; CuI / CH2Cl2 / 6 h / 65 °C
View Scheme
chlormethiazole
533-45-9

chlormethiazole

2-(Z)-6-(E)-2-(2-chloroethyl)-3-methyl-6-pentyl-4H-[1,4]-thiazepin-5-one

2-(Z)-6-(E)-2-(2-chloroethyl)-3-methyl-6-pentyl-4H-[1,4]-thiazepin-5-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: MeLi / diethyl ether / -40 °C
1.2: 63 percent / I2 / diethyl ether / -40 - 20 °C
2.1: 84 percent / Et3N; Pd(PPh3)2Cl2; CuI / CH2Cl2 / 6 h / 65 °C
3.1: 79 percent / (η6-C6H5BPh3)-Rh+(1,5-COD); (PhO)3P; H2 / CH2Cl2 / 18 h / 110 °C / 15961.1 Torr
View Scheme
chlormethiazole
533-45-9

chlormethiazole

N-Methyl-N-<(Z)-1-(2-thietanylidene)ethyl>formamide
71114-46-0

N-Methyl-N-<(Z)-1-(2-thietanylidene)ethyl>formamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / acetone / 24 h / 20 °C
2: 78 percent / 1 M NaOH / trichloroethene / 0.17 h / Ambient temperature; other 5-ω-chloroalkyl-3-methylthiazolium methosulfates
View Scheme
chlormethiazole
533-45-9

chlormethiazole

bis-[2-(4-methyl-thiazol-5-yl)-ethyl]-disulfide

bis-[2-(4-methyl-thiazol-5-yl)-ethyl]-disulfide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: H2O2; aqueous NaOH
View Scheme
chlormethiazole
533-45-9

chlormethiazole

bis-(2-chloro-ethyl)-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine; dihydrochloride
99548-90-0

bis-(2-chloro-ethyl)-[2-(4-methyl-thiazol-5-yl)-ethyl]-amine; dihydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol
2: HCl; CHCl3 / anschliessend Behandeln mit SOCl2 in CHCl3
View Scheme

Clomethiazole Chemical Properties

5-(2-chloroethyl)-4-methylthiazole (533-45-9) is also named as clomethiazole;chlormethiazole;;ChlormethiazoleHCl;5-(2-Chlorethyl)-4-methylthiazole hydrochloride;Chlorethiazole;Clomethiazolum,and so on.

CAS: 533-45-9
Molecular Formula: C6H8ClNS
Molecular Weight: 161.65
Molecular structure:
EINECS: 208-565-7
Index of Refraction: 1.545 
Molar Refractivity: 41.95 cm3 
Molar Volume: 132.6 cm3 
Polarizability: 16.63 10-24cm3 
Surface Tension: 41.8 dyne/cm 
Density: 1.218 g/cm3 
Flash Point: 102.4 °C 
Enthalpy of Vaporization: 46.33 kJ/mol 
Boiling Point: 245.8 °C at 760 mmHg 
Vapour Pressure: 0.0442 mmHg at 25°C

Clomethiazole Uses

5-(2-chloroethyl)-4-methylthiazole (533-45-9)  is sedative-hypnotic medicine and especially suitable for elderly patients with the treatment of senile insomnia,age-related anxiety, irritability ,and so on.

Clomethiazole Toxicity Data With Reference

1.   

orl-mus LD50:2110 mg/kg

   JMCMAR    Journal of Medicinal Chemistry. 7 (1964),167.
2.   

ipr-mus LD50:190 mg/kg

   APSXAS    Acta Pharmaceutica Suecdca. 8 (1971),39.
3.   

ivn-mus LD50:94 mg/kg

   APSXAS    Acta Pharmaceutica Suecdca. 7 (1970),423.

RTECS: XJ3850000

Clomethiazole Safety Profile

5-(2-chloroethyl)-4-methylthiazole (533-45-9)  is poisonous by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of Cl−, NOx, and SOx.

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