Methimazole supplier | CasNO.60-56-0

Name
Methimazole
EINECS 200-482-4
CAS No. 60-56-0
Article Data31
CAS DataBase
Density 1.28 g/cm³
Solubility soluble in water
Melting Point 144-147 °C(lit.)
Formula C₄H₆N₂S
Boiling Point 154.8 °C at 760 mmHg
Molecular Weight 114.171
Flash Point 47.4 °C
Transport Information
Appearance White Solid
Safety 26-27-45-36/37
Risk Codes 43-62-63
Molecular Structure
Hazard Symbols Xn
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

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

: 33252-29-8
6-chloro-pyridine-2-carbonitrile

: 60-56-0
2-Mercapto-1-methylimidazole

: 2-Cyano-6-(1-methyl-1H-imidazol-2-yl)thiopyridine

Conditions

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 70℃; for 18h;	100%

: 99519-64-9
1-bromo-3-(4-chloro-phenyl)-3-methyl-butan-2-one

: 60-56-0
2-Mercapto-1-methylimidazole

: 1185752-50-4
3-(4-chloro-phenyl)-3-methyl-1-(1-methyl-1H-imidazol-2-ylsulfanyl)-butan-2-one

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 72434-98-1
1-iodo-(Z)-11-eicosene

: 60-56-0
2-Mercapto-1-methylimidazole

: C24H44N2S*HI

Conditions

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness; Inert atmosphere;	100%

: (Z)-16-iodohexadec-7-ene

: 60-56-0
2-Mercapto-1-methylimidazole

: C20H36N2S*HI

Conditions

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness; Inert atmosphere;	100%

: 73120-38-4, 69674-78-8
oleyl iodide

: 60-56-0
2-Mercapto-1-methylimidazole

: HI*C22H40N2S

Conditions

Conditions	Yield
In acetonitrile at 40 - 45℃; for 72h; Darkness;	100%

: 42599-17-7
(E)-1-iodo-1-octene

: 60-56-0
2-Mercapto-1-methylimidazole

: (E)-1-methyl-2-(oct-1-enylthio)-1H-imidazole

Conditions

Conditions	Yield
With potassium phosphate; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate In toluene at 110℃; for 24h;	99%

: 15278-97-4
(trimethylphosphine)gold(I) chloride

: 60-56-0
2-Mercapto-1-methylimidazole

: 1355252-24-2
(C3H3N2(CH3)S)(trimethylphosphine gold(I))

Conditions

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

: 15529-90-5
(triethylphosphine)chlorogold(I)

: 60-56-0
2-Mercapto-1-methylimidazole

: 1355252-25-3
(C3H3N2(CH3)S)(triethylphosphine gold(I))

Conditions

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

: 14243-64-2
(triphenylphosphine)gold(I) chloride

: 60-56-0
2-Mercapto-1-methylimidazole

: 1355252-26-4
(C3H3N2(CH3)S)(triphenylphosphine gold(I))

Conditions

Conditions	Yield
With NaOH In methanol to thiol-compd. in CH3OH NaOH added, stirred for 5 min at room temp., Au-compd. added, stirred for 1 h; evaporated in vac., elem. anal.;	99%

: 70314-82-8
N-(2,4-dimethylphenyl)-2,2,2-trifluoroethanimidoyl chloride

: 60-56-0
2-Mercapto-1-methylimidazole

: 1-(1-((2,4-dimethylphenyl)imino)-2,2,2-trifluoroethyl)-3-methyl-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With sodium hydride In acetonitrile at 25℃; for 0.5h; Stage #2: N-(2,4-dimethylphenyl)-2,2,2-trifluoroethanimidoyl chloride In acetonitrile at 25℃; for 9h;	99%

: 69563-07-1
2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride

: 60-56-0
2-Mercapto-1-methylimidazole

: 1-methyl-3-(2,2,2-trifluoro-1-((3-(trifluoromethyl)phenyl)imino)ethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With sodium hydride In acetonitrile at 25℃; for 0.5h; Stage #2: 2,2,2-trifluoro-N-(3-(trifluoromethyl)phenyl)acetimidoyl chloride In acetonitrile at 25℃; for 9h;	99%

: 762-42-5
dimethyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: 60-56-0
2-Mercapto-1-methylimidazole

: dimethyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	98%

...Expand

: 14447-03-1
Diisopropyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: 60-56-0
2-Mercapto-1-methylimidazole

: diisopropyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	98%

...Expand

: 1087-09-8
1,4-diphenyl-but-2-yne-1,4-dione

: 60-56-0
2-Mercapto-1-methylimidazole

: 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-1,4-diphenylbutane-1,4-dione

Conditions

Conditions	Yield
With triphenylphosphine	98%

: 78056-39-0
4,5-difluoro-2-nitroaniline

: 60-56-0
2-Mercapto-1-methylimidazole

: 849236-50-6
5-(1-methyl-1H-imidazol-2-ylthio)-4-fluoro-2-nitrobenzenamine

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 5h;	98%

: 14242-05-8
silver perchlorate monohydrate

: 37095-27-5
(bis(diphenylphosphino)methane)bis(chlorogold(I))

: 60-56-0
2-Mercapto-1-methylimidazole

: [Au2(μ-bis(diphenylphosphino)methane)(2-mercapto-1-methylimidazole)](ClO4)2

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: AgCl; N2-atmosphere, in dark; addn. of 2 equiv. AgClO4 to Au-complex, standingfor 0.5 h, filtration, addn. of stoich. amt. mercaptoimidazole, standin g for 0.5 h (pptn.); collection (centrifugation); second crop from mother liquor; elem. anal.;	98%

...Expand

: bismuth(III) chloride

: 67-64-1
acetone

: 60-56-0
2-Mercapto-1-methylimidazole

: C16H24Bi2Cl6N8S4*C3H6O

Conditions

Conditions	Yield
In methanol for 3h;	98%

...Expand

: 66086-33-7
Di-tert-butyl acetylenedicarboxylate

: 603-35-0
triphenylphosphine

: 60-56-0
2-Mercapto-1-methylimidazole

: di-tert-butyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	97%

...Expand

: 16940-66-2
sodium tetrahydroborate

: 563-68-8
thallium(I) acetate

: 60-56-0
2-Mercapto-1-methylimidazole

: thallium(I) bis(2-mercapto-1-methylimidazolyl)borate

Conditions

Conditions	Yield
In tetrahydrofuran; methanol; water byproducts: CH3COONa; suspn. of NaBH4 and S compd. in THF refluxed for 15 h under Ar, cooled to room temp., solvent removed in vac., solid dissolved in MeOH, aq. soln. of TlOAc added, stirred for 15 min; filtered, washed with water, dried in vac. for 2.5 h; elem. anal.;	97%

...Expand

: 4225-92-7
2-bromo-1-(2,4,6-trimethylphenyl)ethanone

: 60-56-0
2-Mercapto-1-methylimidazole

: 1154952-09-6
2-(1-methyl-1H-imidazol-2-ylsulfanyl)-1-(2,4,6-trimethyl-phenyl)-ethanone

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	97%

: 1185023-08-8
2-bromo-1-[1-(4-chloro-phenyl)-cyclopropyl]-ethanone

: 60-56-0
2-Mercapto-1-methylimidazole

: 1185751-91-0
1-[1-(4-chloro-phenyl)-cyclopropyl]-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-ethanone

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	97%

: 2043-57-4
1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane

: 60-56-0
2-Mercapto-1-methylimidazole

: C12H9F13N2S*HI

Conditions

Conditions	Yield
In ethanol for 36h; Reflux;	97%

: 155262-17-2
2-fluoro-5-phenyl-3-trifluoromethylthiophene

: 60-56-0
2-Mercapto-1-methylimidazole

: 2-(1-methylimidazol-2-ylmercapto)-5-phenyl-3-trifluoromethylthiophene

Conditions

Conditions	Yield
With potassium hydroxide In 1,4-dioxane Heating;	96%

: 603-35-0
triphenylphosphine

: 60-56-0
2-Mercapto-1-methylimidazole

: 762-21-0
acetylenedicarboxylic acid diethyl ester

: diethyl 2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	96%

...Expand

: 658040-87-0
7-methoxy-2-methylsulfonyl-3-phenyl-4H-1-benzopyran-4-one

: 60-56-0
2-Mercapto-1-methylimidazole

: 7-methoxy-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-3-phenyl-chromen-4-one

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;	96%

: 138286-76-7, 5445-29-4
ethyl-2-bromooctanoate

: 60-56-0
2-Mercapto-1-methylimidazole

: 212769-61-4
2-(1-methyl-1H-imidazol-2-yl-sulfanyl)-octanoic acid ethyl ester

Conditions

Conditions	Yield
	96%
	96%

: 60-56-0
2-Mercapto-1-methylimidazole

: 137048-30-7
1-methyl-1H-imidazole-2-sulfonic acid

Conditions

Conditions	Yield
With chlorine dioxide In water for 0.5h;	96%

: 42599-24-6
E-styryl iodide

: 60-56-0
2-Mercapto-1-methylimidazole

: (E)-1-methyl-2-(styrylthio)-1H-imidazole

Conditions

Conditions	Yield
Stage #1: 2-Mercapto-1-methylimidazole With potassium fluoride; copper(l) iodide; cis-1,2-cyclohexane In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: E-styryl iodide In N,N-dimethyl-formamide at 90℃; for 12h;	96%

: 75-09-2
dichloromethane

: 60-56-0
2-Mercapto-1-methylimidazole

: 133213-39-5
1,1'-methylenebis(1,3-dihydro-3-methyl-1H-imidazole-2-thione)

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 80℃; for 26h; Sealed tube;	95.8%
at 79.84℃; for 24h;	89%

: 60-56-0
2-Mercapto-1-methylimidazole

: 2-Chloromethyl-4-(3,4-dimethoxy-phenyl)-quinoline-3-carboxylic acid ethyl ester

: 4-(3,4-Dimethoxy-phenyl)-2-(1-methyl-1H-imidazol-2-ylsulfanylmethyl)-quinoline-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature;	95%

Methimazole Chemical Properties

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

Methimazole Uses

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

Methimazole 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.

Methimazole Consensus Reports

Reported in EPA TSCA Inventory.

Methimazole Safety Profile

Hazard Codes: Harmful Xn
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 NO_x and SO_x. See also MERCAPTANS.

Methimazole 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.

Product Name

Methimazole

Synthetic route

Methimazole Chemical Properties

Methimazole Uses

Methimazole Toxicity Data With Reference

Methimazole Consensus Reports

Methimazole Safety Profile

Methimazole Specification

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