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60-56-0

Basic Information
CAS No.: 60-56-0
Name: Methimazole
Article Data: 31
Molecular Structure:
Molecular Structure of 60-56-0 (Methimazole)
Formula: C4H6N2S
Molecular Weight: 114.171
Synonyms: 4-Imidazoline-2-thione,1-methyl- (6CI,7CI);Imidazole-2-thiol, 1-methyl- (8CI);1-Methyl-1H-imidazole-2-thiol;1-Methyl-2-mercapto-1H-imidazole;1-Methyl-4-imidazoline-2-thione;1-Methylimidazole-2-thiol;1-Methylimidazole-2-thione;Basolan;Danantizol;Mercaptazole;Mercazole;Mercazolyl;
EINECS: 200-482-4
Density: 1.28 g/cm3
Melting Point: 144-147 °C(lit.)
Boiling Point: 154.8 °C at 760 mmHg
Flash Point: 47.4 °C
Solubility: soluble in water
Appearance: White Solid
Hazard Symbols: HarmfulXn
Risk Codes: 43-62-63
Safety: 26-27-45-36/37
PSA: 56.62000
LogP: 0.70880
Synthetic route
79487-94-8

2-tert-butylthio-1-methyl-1H-imidazole

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
With aluminum (III) chloride at 20℃; Reagent/catalyst; Inert atmosphere;91%
616-47-7

1-methyl-1H-imidazole

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1.5h;
Stage #2: With sulfur In tetrahydrofuran; hexane for 9h; Temperature; Reflux;
82.54%

S-2-(1-methyl)imidazolyl ethanethioate

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 20℃; for 5h; Solvent;77%
63348-55-0

2-(benzylthio)-1-methyl-1H-imidazole

A

23269-08-1

3-methyl-1-benzyl-1,3-dihydroimidazole-2-thione

B

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
In methanol for 5h; Irradiation;A 168 mg
B 88 mg
7647-01-0

hydrogenchloride

333-20-0

potassium thioacyanate

20677-73-0

N-methylaminoacetaldehyde diethyl acetal

60-56-0

2-Mercapto-1-methylimidazole

90203-43-3

N-(2,2-diethoxy-ethyl)-N'-methyl-thiourea

H2SO4 (diluted )

H2SO4 (diluted )

60-56-0

2-Mercapto-1-methylimidazole

3129-90-6

isothiocyanic acid

20677-73-0

N-methylaminoacetaldehyde diethyl acetal

60-56-0

2-Mercapto-1-methylimidazole

2,2'-dithiodi(1-methylimidazole) bis(perchloric acid) salt

A

616-47-7

1-methyl-1H-imidazole

B

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
With Carbonate buffer at 25℃; Kinetics;
333-20-0

potassium thioacyanate

20677-73-0

N-methylaminoacetaldehyde diethyl acetal

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 30℃; Large scale;150 kg
540-72-7

sodium thiocyanide

122-07-6

N-(methyl)aminoacetaldehyde dimethyl acetal

60-56-0

2-Mercapto-1-methylimidazole

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 60℃; pH=1 - 2;0.86 kg
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Chemistry

IUPAC Name: 3-Methyl-1H-imidazole-2-thione
Synonyms of Methimazole (CAS NO.60-56-0): 1,3-Dihydro-1-methyl-2H-imidazole-2-thione ; 1-Methyl-1,3-dihydroimidazole-2-thione ; 1-Methyl-2-mercaptoimidazole ; 1-Methylimidazole-2-thiol ; 2-Mercapto-1-methylimidazole ; 4-Imidazoline-2-thione, 1-methyl- ; Favistan ; Mercazolylum ; N-Methyl-2-mercaptoimidazole
CAS NO: 60-56-0
Molecular Formula: C4H6N2S
Molecular Weight: 114.16
Molecular Structure:
EINECS: 200-482-4
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 38.57 Å2
Index of Refraction: 1.666
Molar Refractivity: 33.07 cm3
Molar Volume: 88.8 cm3
Surface Tension: 61.9 dyne/cm
Density: 1.28 g/cm3
Flash Point: 47.4 °C
Enthalpy of Vaporization: 39.15 kJ/mol
Boiling Point: 154.8 °C at 760 mmHg
Vapour Pressure: 3.13 mmHg at 25°C
Melting point: 140-145 °C
Water solubility: soluble
Appearance: White Solid
SMILES: S=C1N(\C=C/N1)C
InChI: InChI=1/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChIKey: PMRYVIKBURPHAH-UHFFFAOYAN
Std. InChI: InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
Std. InChIKey: PMRYVIKBURPHAH-UHFFFAOYSA-N
SMILES: S=C1N(\C=C/N1)C
InChI: InChI=1/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChIKey: PMRYVIKBURPHAH-UHFFFAOYAN
Std. InChI: InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
Std. InChIKey: PMRYVIKBURPHAH-UHFFFAOYSA-N
Product Categories of Methimazole (CAS NO.60-56-0): Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals

Uses

 Methimazole (CAS NO.60-56-0) is used as a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 860mg/kg (860mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
mouse LD50 subcutaneous 345mg/kg (345mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
rat LD50 oral 2250mg/kg (2250mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
rat LD50 subcutaneous 1050mg/kg (1050mg/kg)   Farmaco, Edizione Scientifica. Vol. 14, Pg. 54, 1959.
women TDLo oral 13mg/kg/33D-I (13mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EAR

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: OTHER CHANGES
Clinical Endocrinology Vol. 51, Pg. 667, 1999.
women TDLo oral 492mg/kg/88W- (492mg/kg) ENDOCRINE: CHANGE IN GONADOTROPINS

BLOOD: AGRANULOCYTOSIS
Netherlands Journal of Medicine. Vol. 43, Pg. 71, 1993.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 43-62-63
43: May cause sensitization by skin contact
62: Possible risk of impaired fertility
63: Possible risk of harm to the unborn child
Safety Statements: 26-27-45-36/37
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
RTECS: NI8615000
HS Code: 29332990
Poison by subcutaneous route. Moderately toxic by ingestion and intraperitoneal routes. Human teratogenic effects. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. An antithyroid drug. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container.