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Carbimazole

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Name

Carbimazole

EINECS 244-854-4
CAS No. 22232-54-8 Density 1.31 g/cm3
PSA 68.25000 LogP 1.56070
Solubility Soluble in water, ethanol, chloroform and acetone. Sightly soluble in water. Melting Point 124 °C
Formula C7H10N2O2S Boiling Point 240.4 °C at 760 mmHg
Molecular Weight 186.235 Flash Point 99.2 °C
Transport Information N/A Appearance N/A
Safety 22-36/37/39 Risk Codes 22-36-43
Molecular Structure Molecular Structure of 22232-54-8 (Carbimazole) Hazard Symbols N/A
Synonyms

4-Imidazoline-1-carboxylicacid, 3-methyl-2-thioxo-, ethyl ester (6CI,8CI);1-Ethoxycarbonyl-3-methyl-2-thio-4-imidazoline;1-Methyl-3-carbethoxy-2-thioglyoxalone;3-Carbethoxymercapto-1-methylimidazole;3-Carbethoxythio-1-methylglyoxaline;3-Carbethoxythio-1-methyliminazole;Athyromazole;Basolest;CG 1;Carbethoxymethimazole;Ethyl 3-methyl-2-thioimidazoline-1-carboxylate;Ethyl 3-methyl-2-thioxo-D4-imidazoline-1-carboxylate;Neo-Thyreostat;Neomercazole;Tyrazol;

Article Data 5

Carbimazole Synthetic route

616-47-7

1-methyl-1H-imidazole

541-41-3

chloroformic acid ethyl ester

22232-54-8

carbimazole

Conditions
ConditionsYield
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃;
Stage #2: With sulfur In tetrahydrofuran; hexane at 25℃; for 12h;
Stage #3: chloroformic acid ethyl ester In tetrahydrofuran; hexane at 0℃;
88%
110-86-1

pyridine

60-56-0

1-methyl-1,3-dihydro-imidazole-2-thione

541-41-3

chloroformic acid ethyl ester

22232-54-8

carbimazole

60-56-0

1-methyl-1,3-dihydro-imidazole-2-thione

541-41-3

chloroformic acid ethyl ester

22232-54-8

carbimazole

Conditions
ConditionsYield
With pyridine
497-98-3

2-ethoxycarbonylsulfanyl-1-methyl-1H-imidazole

60-29-7

diethyl ether

628-13-7

pyridine hydrochloride

22232-54-8

carbimazole

497-98-3

2-ethoxycarbonylsulfanyl-1-methyl-1H-imidazole

60-29-7

diethyl ether

541-41-3

chloroformic acid ethyl ester

22232-54-8

carbimazole

497-98-3

2-ethoxycarbonylsulfanyl-1-methyl-1H-imidazole

22232-54-8

carbimazole

Conditions
ConditionsYield
With diethyl ether; chloroformic acid ethyl ester
With diethyl ether; pyridine hydrochloride

C7H12N2O2*ClH

22232-54-8

carbimazole

Conditions
ConditionsYield
Stage #1: C7H12N2O2*ClH With triethylamine In tetrahydrofuran at 0 - 25℃;
Stage #2: With sulfur In tetrahydrofuran at 25℃; for 24h;
0.44 g
22232-54-8

carbimazole

A

61640-28-6

1-ethyl-3-methyl-1H-imidazole-2(3H)-thione

B

50968-13-3

2-ethylsulfanyl-1-methyl-1H-imidazole

22232-54-8

carbimazole

3-Methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid ethyl ester; compound with iodine

Conditions
ConditionsYield
With iodine In tetrachloromethane Equilibrium constant; formation of charge-transfer (with I2) and hydrogen-bonding (with 4-fluorophenol) complexes; formation constant; other solvents; IR and UV study;
22232-54-8

carbimazole

118800-65-0

1-ethyl-2-ethylsulfanyl-3-methyl-imidazolium; iodide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 150 - 160 °C
2: acetone
View Scheme

Carbimazole Specification

The Carbimazole, with the CAS registry number 22232-54-8, is also known as Neomercazole. Its EINECS registry number is 244-854-4. This chemical's molecular formula is C7H10N2O2S and molecular weight is 186.23. Its IUPAC name is called ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate. Carbimazole is used to treat hyperthyroidism. Carbimazole is a pro-drug as after absorption it is converted to the active form, methimazole. Therapy for hyperthyroidism generally starts at a high daily dose of 15 - 40mg continued until the patient has normal thyroid function, and then reduced to a maintenance dose of 5 - 15mg. Treatment is usually given for 12 - 18 months followed by a trial withdraw. The product should be sealed and stored in cool and dry place.

Physical properties of Carbimazole: (1)ACD/LogP: 0.34; (2)ACD/LogD (pH 5.5): 0.34; (3)ACD/LogD (pH 7.4): 0.34; (4)ACD/BCF (pH 5.5): 1.06; (5)ACD/BCF (pH 7.4): 1.06; (6)ACD/KOC (pH 5.5): 36.38; (7)ACD/KOC (pH 7.4): 36.38; (8)#H bond acceptors: 4; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.611; (12)Molar Refractivity: 49.05 cm3; (13)Molar Volume: 141.1 cm3; (14)Surface Tension: 60.2 dyne/cm; (15)Density: 1.31 g/cm3; (16)Flash Point: 99.2 °C; (17)Enthalpy of Vaporization: 47.73 kJ/mol; (18)Boiling Point: 240.4 °C at 760 mmHg; (19)Vapour Pressure: 0.038 mmHg at 25°C.

Preparation: this chemical can be prepared from amination, cyclization and condensation reaction. This reaction's raw raw materials are ethanediol and chlorinated acetaldehyde. It also will need armour amine, methanol, hydrochloric acid, thiocyanate potassium, pyridine and chlorine formic acid ethyl ester.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes. May cause sensitisation by skin contact. You should not breathe its dust. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCOC(=O)N1C=CN(C1=S)C
(2)InChI: InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
(3)InChIKey: CFOYWRHIYXMDOT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 23mg/kg/5W-I (23mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" Journal of the Royal Society of Medicine. Vol. 78, Pg. 75, 1985.
women TDLo oral 25mg/kg/6W-I (25mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Archives of Internal Medicine. Vol. 145, Pg. 1513, 1985.
women TDLo oral 703mg/kg/17W- (703mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR

SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR
British Medical Journal. Vol. 309, Pg. 929, 1994.
women TDLo parenteral 1mg/kg/1D-I (1mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" New England Journal of Medicine. Vol. 309, Pg. 438, 1983.

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