Methylthiouracil supplier

Name
Methylthiouracil
EINECS 200-252-3
CAS No. 56-04-2
Article Data62
CAS DataBase
Density 1.36 g/cm³
Solubility INSOLUBLE
Melting Point ~330 °C (dec.)(lit.)
Formula C₅H₆N₂OS
Boiling Point 342.3 °C at 760 mmHg
Molecular Weight 142.181
Flash Point 160.8 °C
Transport Information
Appearance white powder
Safety 36/37-45
Risk Codes 22-40
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Uracil,6-methyl-2-thio- (8CI);2-Mercapto-4-methyl-6-hydroxypyrimidine;2-Mercapto-6-methyl-4-pyrimidinol;2-Mercapto-6-methylpyrimidyl-4-one;2-Thio-6-methyluracil;4-Hydroxy-2-mercapto-6-methylpyrimidine;4-Methyl-2-thiouracil;6-Methyl-2-thiouracil;6-Methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine;Alkiron;Basecil;Methiacil;Methicil;Methiocil;Muracil;NSC 193526;NSC 9378;Prostrumyl;Thimecil;Thiomidil;Thioryl;Thiothyron;Thiuryl;Thyreostat;Thyreostat I;Tiotiron;USAF-EK 6454;
PSA 80.74000
LogP 0.74090

Synthetic route

: 141-97-9
ethyl acetoacetate

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 125℃; under 15514.9 Torr; for 0.416667h; Biginelli condensation; Microwave irradiation; Inert atmosphere;	94.6%
With potassium hydroxide In ethanol at 80℃; for 5h;	91%
With sodium formate In methanol for 7h; Heating;	90%

: 72324-39-1
5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
Stage #1: 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione With alcohol Microwave irradiation; Stage #2: thiourea for 0.05h; Microwave irradiation;	70%

: 105-45-3
acetoacetic acid methyl ester

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
for 0.0666667h; microwave irradiation;	62%
In dimethylsulfoxide-d6 at 22 - 28℃; Mechanism;
Heating;

: 119730-09-5
2-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}-6-methylpyrimidin-4(3H)-one

A: 56-04-2
6-methyl-2-thiouracil

B: 8-(4-bromobenzoyl)-6-(4-bromophenyl)-4-methyl-7-[(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)methyl]pirrolo[1,2-a]pyrimidin-2(1H)-one

C: 119730-50-6
(E,Z)-2-[2-(4-bromophenyl)-2-oxoethylidene]-6-methyl-2,3-dihydropyrimidin-4(1H)-one

Conditions

Conditions	Yield
at 180 - 200℃; neat (no solvent);	A 47% B 16% C 9%

...Expand

: 17649-31-9
6-methyl-2-((2-oxo-2-phenylethyl)thio)pyrimidin-4(3H)-one

A: 56-04-2
6-methyl-2-thiouracil

B: 1380547-50-1
8-benzoyl-4-methyl-7-[(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)methyl]-6-phenylpyrrolo[1,2-a]pyrimidin-2(1H)-one

C: 119730-48-2
(E,Z)-6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dyhydropyrimidin-4(1H)-one

Conditions

Conditions	Yield
at 180 - 200℃; neat (no solvent);	A n/a B 21% C 12%

...Expand

: 674-82-8
4-methyleneoxetan-2-one

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

: 124-41-4
sodium methylate

: 141-97-9
ethyl acetoacetate

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With methanol

...Expand

: 141-78-6
ethyl acetate

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With sodium

: 1007476-32-5
sodium ethyl acetylacetate enolate

: 17356-08-0
thiourea

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With paraffin oil

: 35523-75-2
7-methyl-5H-1,3,4-thiadiazolo<3,2-a>pirimidin-5-one

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 336h; Ambient temperature;

: 6328-58-1
4-Hydroxy-6-methyl-2-methylthiopyrimidine

A: 3524-87-6
6-methyl-3H-pyrimidin-4-one

B: 626-48-2
6-Methyluracil

C: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
In water for 2h; Irradiation;

...Expand

β-<6-oxy-4-methyl-pyrimidyl-(2)-mercapto>-α-hydroxyimino-propionic acid: β-<6-oxy-4-methyl-pyrimidyl-(2)-mercapto>-α-hydroxyimino-propionic acid

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With formic acid; zinc

β-thioureido-crotonic acid ethyl ester: β-thioureido-crotonic acid ethyl ester

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With sodium ethanolate

6-oxy-2-<β-hydroxyimino-β-phenyl-ethylsulfanyl>-4-methyl-pyrimidine: 6-oxy-2-<β-hydroxyimino-β-phenyl-ethylsulfanyl>-4-methyl-pyrimidine

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With sodium amalgam; ethanol
With ethanol; aluminium amalgam
With ammonium hydroxide; iron(II) sulfate
With formic acid; zinc

6-oxy-2-<β-phenylhydrazono-β-phenyl-ethylsulfanyl>-4-methyl-pyrimidine: 6-oxy-2-<β-phenylhydrazono-β-phenyl-ethylsulfanyl>-4-methyl-pyrimidine

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With sodium amalgam; ethanol
With ethanol; aluminium amalgam

6-oxy-2--4-methyl-pyrimidine: 6-oxy-2--4-methyl-pyrimidine

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With ethanol; aluminium amalgam
With acetic acid; phenylhydrazine at 100℃;

6-oxy-2-ethylsulfanyl-pyrimidin-acetic acid-(4): 6-oxy-2-ethylsulfanyl-pyrimidin-acetic acid-(4)

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With hydrogenchloride at 170℃;

: 17356-08-0
thiourea

: 105-53-3
diethyl malonate

: 56-04-2
6-methyl-2-thiouracil

Conditions

Conditions	Yield
With potassium hydroxide In ethanol

: 56-04-2
6-methyl-2-thiouracil

: 626-48-2
6-Methyluracil

Conditions

Conditions	Yield
With sodium hydroxide; methyloxirane In water at 20℃;	100%
With potassium tert-butylate; iodine In tert-butyl alcohol for 30h; Heating;	95%
With potassium superoxide; 18-crown-6 ether In N,N-dimethyl-formamide for 72h; Ambient temperature;	79%

: 56-04-2
6-methyl-2-thiouracil

: 556-56-9
allyl iodid

: 62459-06-7
2-allylsulfanyl-6-methylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 50℃; Kinetics; Further Variations:; Solvents; Reaction partners;	99%

: 56-04-2
6-methyl-2-thiouracil

: 100-39-0
benzyl bromide

: 3019-17-8
2-(benzylsulfanyl)-6-methylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 50℃; for 0.25h; Kinetics; Further Variations:; Temperatures; Reaction partners; Solvents;	99%
With 1-ethyl-3-methylimidazolium acetate at 65℃; for 3h; regiospecific reaction;

: 56-04-2
6-methyl-2-thiouracil

: 121134-48-3
1,1-dibromo-1-decene

: 1279713-34-6
(Z)-2-(1-bromodec-1-en-2-ylthio)-6-methylpyrimidin-4(1H)-one

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In water; N,N-dimethyl-formamide at 65℃; for 12h; Inert atmosphere; stereoselective reaction;	99%

: 56-04-2
6-methyl-2-thiouracil

: 6308-38-9
2,4-dithio-6-methyluracil

Conditions

Conditions	Yield
With diphosphorus pentasulfide; sodium hydrogencarbonate In diethylene glycol dimethyl ether at 110℃; for 2h;	98%
With tetraphosphorus decasulfide; silica gel for 0.333333h; microwave irradiation;	40%
With tetraphosphorus decasulfide; tetralin at 170℃;
With tetraphosphorus decasulfide; xylene at 155℃;
With tetraphosphorus decasulfide at 200℃;

: 56-04-2
6-methyl-2-thiouracil

: 74-88-4
methyl iodide

: 6328-58-1
6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 4h;	98%
With water; sodium hydroxide at 20℃; for 1h; Cooling with ice;	86%
Stage #1: 6-methyl-2-thiouracil With sodium hydroxide In water for 0.5h; Stage #2: methyl iodide In water at 10 - 20℃; for 24h;	54%
With potassium carbonate In dimethyl sulfoxide	48%
With potassium hydroxide In methanol for 0.166667h; Ambient temperature;

: 56-04-2
6-methyl-2-thiouracil

: 21040-45-9
Cinnamyl acetate

: 180145-62-4
2-<(E)-cinnamylthio>-6-methyl-4(3H)-pyrimidinone

Conditions

Conditions	Yield
With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water at 60℃; for 20h;	98%

: 56-04-2
6-methyl-2-thiouracil

: 7131-09-1
1-(4-(bromomethyl)phenyl)adamantane

: 911838-00-1
2-[4-(1-adamantyl)benzylsulfanyl]-6-methyl-pyrimidin-4(3H)-one

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 50℃; Kinetics; Further Variations:; Temperatures;	97%

: 56-04-2
6-methyl-2-thiouracil

: 7338-94-5
1,3-diphenyl-2-propynone

: 6-methyl-2-{[(Z)-3-oxo-1,3-diphenyl-1-propenyl]sulfanyl}-4(3H)-pyrimidinone

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 4h; regioselective reaction;	97%

: 56-04-2
6-methyl-2-thiouracil

sulphur: sulphur

: 626-48-2
6-Methyluracil

Conditions

Conditions	Yield
With potassium tert-butylate; iodine In tert-butyl alcohol for 30h; Heating; further halogen as catalysts;	95%

: 56-04-2
6-methyl-2-thiouracil

A: 626-48-2
6-Methyluracil

B sulphur: sulphur

Conditions

Conditions	Yield
With potassium tert-butylate; iodine In tert-butyl alcohol for 30h; Product distribution; conversion of thiocarbonyl compounds into their corresponding oxygen analogues using alkoxides and hydroxide with halogens as catalysts;	A 95% B n/a

: 56-04-2
6-methyl-2-thiouracil

: 106-96-7
propargyl bromide

: 6-methyl-1N-propargyl-2-thiouracil

Conditions

Conditions	Yield
Stage #1: 6-methyl-2-thiouracil With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Substitution; Heating; Stage #2: propargyl bromide In acetonitrile for 8h; Substitution; Heating;	95%

: 56-04-2
6-methyl-2-thiouracil

: 107-08-4
1-iodo-propane

: 62459-04-5
6-methyl-2-propylsulfanylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 50℃; Kinetics; Further Variations:; Temperatures;	94%

: 110-85-0
piperazine

: 56-04-2
6-methyl-2-thiouracil

: 50-00-0
formaldehyd

: 75682-14-3
C-5,N-3-Dipiperazinomethylene-6-methyl-2-thiouracil

Conditions

Conditions	Yield
In ethanol; water for 24h; Ambient temperature;	93.1%

...Expand

: 56-04-2
6-methyl-2-thiouracil

: 106625-69-8
ethyl (E)-3-phenyl-2-propenyl carbonate

: 2-<(E)-cinnamylthio>-3-<(E)-cinnamyl>-6-methylpyrimidin-4-one

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 1,4-di(diphenylphosphino)-butane In tetrahydrofuran; water at 60℃; for 17h;	92%

: 56-04-2
6-methyl-2-thiouracil

: 6-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-sulfonyl chloride

Conditions

Conditions	Yield
With chlorosulfonic acid In chloroform at 0℃; for 0.5h;	92%

: 56-04-2
6-methyl-2-thiouracil

: 185-80-8
1-oxa-2-azaspiro[2.5]octane

: 5a-Amino-2-methyl-5a,6,7,8,9,9a-hexahydro-4H-pyrimido<2,1-b>benzothiazol-4-on

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; toluene for 12h; Ambient temperature;	91%

: 56-04-2
6-methyl-2-thiouracil

: 21985-04-6
3-phenyl-1-(2-thienyl)-2-propyn-1-one

: 6-methyl-2-{[(Z)-3-oxo-1-phenyl-3-(2-thienyl)-1-propenyl]sulfanyl}-4(3H)-pyrimidinone

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 4h; regioselective reaction;	91%

: 56-04-2
6-methyl-2-thiouracil

: 532-27-4
1-chloroacetophenone

: 86869-48-9
5-(4-Chloro-phenyl)-3H-thiazol-2-one

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 2h; Heating;	90%

: 56-04-2
6-methyl-2-thiouracil

: 29310-88-1
3-bromoacetylcoumarin

: 1233880-54-0
5-methyl-3-[(3'-coumarinyl)]-7H-[1,3]-thiazolo-[3,2-a]-pyrimidine-7-one

Conditions

Conditions	Yield
at 125℃; for 0.0216667h; Microwave irradiation;	90%

: 56-04-2
6-methyl-2-thiouracil

: 1124-39-6
4-ethylcatechol

: 2-(2-ethyl-4,5-dihydroxyphenylthio)-6-methylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
With laccase from Agaricus bisporus In aq. phosphate buffer; ethanol at 20℃; for 14h; pH=6; Green chemistry; Enzymatic reaction; chemoselective reaction;	90%

: 56-04-2
6-methyl-2-thiouracil

: glycyrrhizic acid

: C42H62O16*C5H6N2OS

Conditions

Conditions	Yield
In ethanol; water at 50 - 60℃; for 2h; complex formation;	89%

: 56-04-2
6-methyl-2-thiouracil

: (hydrotris(3-p-cumenylmethylpyrazolyl)borate)Zn(OH)

: (tris(3-cumenyl-5-methylpyrazolyl)borate)Zn(6-methyl-2-thiouracilate)

Conditions

Conditions	Yield
In methanol; dichloromethane addn. of 1 equiv. ligand (in MeOH) to Zn-complex (in CH2Cl2), stirring for 5 h; vol. reduction (vac.), crystn. (4 h), collection (filtration), drying (vac.); elem. anal.;	89%

: 56-04-2
6-methyl-2-thiouracil

: 88735-43-7
2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one

: 1233880-58-4
5-methyl-3-[(5,6-benzo-(3'-coumarinyl))]-7H-[1,3]-thiazolo-[3,2-a]-pyrimidine-7-one

Conditions

Conditions	Yield
at 125℃; for 0.04h; Microwave irradiation;	89%

: 56-04-2
6-methyl-2-thiouracil

: 119730-17-5
6-methyl-2-((2-(4-nitrophenyl)-2-oxoethyl)thio)pyrimidin-4(3H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	87.78%

: 56-04-2
6-methyl-2-thiouracil

: 87-52-5
3-(Dimethylaminomethyl)indole

: N(1')-(3-methylindole)-6'-methyl-2'-thiouracil

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Reflux;	87%

: 56-04-2
6-methyl-2-thiouracil

: 119730-10-8
2-((2-(4-chlorophenyl)-2-oxoethyl)thio)-6-methylpyrimidin-4(3H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	86.85%

: 56-04-2
6-methyl-2-thiouracil

: 6-methyl-2-((2-(3-nitrophenyl)-2-oxoethyl)thio)pyrimidin-4(3H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	86.27%

: 56-04-2
6-methyl-2-thiouracil

: 37746-78-4
4-bromo-trans-crotonic acid ethyl ester

: (7-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-yl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.08333h;	86%

Methylthiouracil Consensus Reports

IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 53.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Methylthiouracil Specification

The Methylthiouracil, also known as 4-Hydroxy-2-mercapto-6-methylpyrimidine, is an organic compound with the formula C₅H₆N₂OS. It belongs to the product category of Pyrimidine. Its EINECS registry number is 200-252-3. With the CAS registry number 56-04-2, its IUPAC name is 6-methyl-2-sulfanylidene-1H-pyrimidin-4-one. What's more, this chemical is a white powder. It is mainly used as surgical preparation of mild hyperthyroidism, thyroid storm, hyperthyroidism and postoperative treatment.

Physical properties of Methylthiouracil: (1)ACD/LogP: 0.31; (2)ACD/LogD (pH 5.5): 0.31; (3)ACD/LogD (pH 7.4): 0.24; (4)ACD/BCF (pH 5.5): 1.01; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 35.06; (7)ACD/KOC (pH 7.4): 29.79; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)Index of Refraction: 1.638; (11)Molar Refractivity: 37.36 cm³; (12)Molar Volume: 103.9 cm³; (13)Surface Tension: 63 dyne/cm; (14)Density: 1.36 g/cm³; (15)Flash Point: 160.8 °C; (16)Enthalpy of Vaporization: 60.93 kJ/mol; (17)Boiling Point: 342.3 °C at 760 mmHg; (18)Vapour Pressure: 3.83E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by acetoacetic acid ethyl ester and thiourea. This reaction will need 4 min with microwave irradiation. The yield is about 69%.

Methylthiouracil can be prepared by acetoacetic acid ethyl ester and thiourea

Uses of Methylthiouracil: The drug acts to decrease the formation of stored thyroid hormone, as thyroglobulin in the thyroid gland. The clinical effects of the drug to treat the hyperthyroid state can have a lag period of up to two weeks, depending on the stores of thyroglobulin and other factors.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It may cause inflammation to the skin or other mucous membranes. In addition, it is harmful if swallowed. Whenever you will contact it, please wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC(=O)NC(=S)N1
(2)InChI: InChI=1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)
(3)InChIKey: HWGBHCRJGXAGEU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	200mg/kg (200mg/kg)		National Technical Information Service. Vol. AD277-689,
mouse	LD50	oral	2125mg/kg (2125mg/kg)		Pharmaceutical Chemistry Journal Vol. 30, Pg. 320, 1996.
rabbit	LDLo	oral	2500mg/kg (2500mg/kg)		"Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 963, 1989.
rat	LD50	intraperitoneal	920mg/kg (920mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Farmaco, Edizione Scientifica. Vol. 13, Pg. 882, 1958.
rat	LD50	oral	1500mg/kg (1500mg/kg)		Nature. Vol. 157, Pg. 659, 1946.

Product Name

Methylthiouracil

Synthetic route

Methylthiouracil Consensus Reports

Methylthiouracil Specification

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