6-methyl-2-thioxo-1H-pyrimidin-4-one
6-methyl-2-thioxo-1H-pyrimidin-4-one
CAS: 56-04-2
Molecular Formula: C5H6N2OS
6-methyl-2-thioxo-1H-pyrimidin-4-one - Names and Identifiers
6-methyl-2-thioxo-1H-pyrimidin-4-one - Physico-chemical Properties
| Molecular Formula | C5H6N2OS |
| Molar Mass | 142.18 |
| Density | 1.291 (estimate) |
| Melting Point | ~330°C (dec.)(lit.) |
| Boling Point | 342.3°C at 760 mmHg |
| Flash Point | 160.8°C |
| Water Solubility | INSOLUBLE |
| Solubility | Easily soluble in ammonia solution and sodium hydroxide solution, slightly soluble in alcohol, ether and acetone, very slightly soluble in water and ether, insoluble in benzene and chloroform |
| Vapor Presure | 3.83E-05mmHg at 25°C |
| Appearance | Solid |
| Color | Clear colorless to yellow |
| Merck | 14,6128 |
| BRN | 115648 |
| pKa | pKa 8.2 (Uncertain) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Stability | Stability Incompatible with strong oxidizing agents, iodine, metals. |
| Refractive Index | 1.6430 (estimate) |
| MDL | MFCD00006040 |
| Physical and Chemical Properties | White crystals. Decomposition at 326-331 °c. Soluble in ammonia solution and sodium hydroxide solution, slightly soluble in alcohol and acetone, very slightly soluble in water and ether, insoluble in benzene and chloroform. Saturated aqueous solution is neutral or slightly acidic to litmus. No smell, bitter, easy sublimation. |
| Use | Intermediates of the cardiovascular drug dipyridamole. |
| In vitro study | Methylthiouracil can reduce the formation of stored thyroid hormones, as well as thyroglobulin in the thyroid gland. Methylthiouracil is also used in conjunction with radioactive iodine. |
6-methyl-2-thioxo-1H-pyrimidin-4-one - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | YR0875000 |
| TSCA | Yes |
| HS Code | 29335995 |
| Hazard Note | Irritant/Possible Carcinogen |
| Toxicity | MLD in rabbits (mg/kg): 2486 orally (Simon) |
6-methyl-2-thioxo-1H-pyrimidin-4-one - Reference
| Reference Show more | 1. Zhu, Zhenjun, et al. "Hypolipidemic effect of Youcha in hyperlipidemia rats induced by high-fat diet." Food & function 8.4 (2017): 1680-1687.https://doi.org/10.1039/C7FO00089H 2. Shan Shi, Ziying Liu, Zhengyuan Xue, Xiaohui Chen, Yang Chu,A plasma metabonomics study on the therapeutic effects of the Si-miao-yong-an decoction in hyperlipidemic rats,Journal of Ethnopharmacology,Volume 256,2020,112780,ISSN 0378-8741,https://doi 3. [IF=4.36] Shan Shi et al."A plasma metabonomics study on the therapeutic effects of the Si-miao-yong-an decoction in hyperlipidemic rats."J Ethnopharmacol. 2020 Jun;256:112780 |
6-methyl-2-thioxo-1H-pyrimidin-4-one - Introduction
Decomposed at 326-331 ℃, the saturated aqueous solution is neutral or slightly acidic to litmus, has no smell, tastes bitter, and is easy to sublimate.
Last Update：2022-10-16 17:26:23
6-methyl-2-thioxo-1H-pyrimidin-4-one - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2B (Vol. Sup 7, 79) 2001 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | methylthiouracil, Chinese alias 6-methyl-2-thiouracil, is an important pharmaceutical Intermediate; not only has antibacterial activity, but also can be used to treat hyperthyroidism. It inhibits the production of thyroxine by inhibiting the peroxidase system in the thyroid gland, so as to achieve the effect of treating hyperthyroidism. Therefore, it is of great significance to optimize the synthesis process. The current synthesis method is mainly acetoacetic acid ethyl ester and thiourea in alkaline conditions catalyzed condensation, commonly used catalyst for sodium alkoxide. |
| preparation | with ethyl acetoacetate and thiourea as starting materials, the ring is synthesized by dehydration, dealcoholization and condensation of amine ketone, thus, 6-methyl-2-thiouracil was obtained. The specific steps are as follows: 250g (7.00 mol) thiourea, 12g(0.09 mol) potassium hydroxide and 80 mL ethanol are added to 0.21 mL three bottles in sequence, and the mixture is stirred for 0.5 h at 70 ℃, the solids were all dissolved. After cooling to room temperature, ethyl acetoacetate was slowly added dropwise and then heated to 70 ° C. For 2 hours. After cooling, water was added to dissolve. Then 36% hydrochloric acid to adjust pH = 4, stirred for 1 h, filtered, washed with 20 mL × 2 water, recrystallized with water, white crystals of 6-methyl -2-thiouracil, the yield was 96.64%, m.P.> 300 ℃ |
| biological activity | methylthiouraci (NSC-193526, NSC-9378) is an antithyroid drug. Methylthiouraci inhibited the production of TNF-α and IL-6 and the activation of NF-κB and ERK1/2. |
| Target | Value |
| Use | an intermediate of the cardiovascular drug Dipyridamole. |
| production method | is obtained by reacting ethyl acetoacetate with thiourea. Thiourea was dissolved in sodium hydroxide solution, ethyl acetoacetate was added dropwise, and the temperature was controlled below 37 °c. After 2h of reaction, water and activated carbon were added and decolorized at 70-80 ℃ for 0.5h. The filtrate was filtered and acidified to pH4-5 with hydrochloric acid, cooled to room temperature, filtered and washed. The filter cake was recrystallized with water to obtain the finished product. The yield was 66%. In production, ethyl acetoacetate and thiourea can also be mixed first, and then sodium oxide solution can be added dropwise. Anhydrous sodium carbonate can also be used instead of sodium hydroxide, and the yield is approximately the same. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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View History
6-methyl-2-thioxo-1H-pyrimidin-4-one
2-methylthieno[3,2-d]pyrimidin-4-ol
6-BroMo-5-fluoro-nicotinic acid Methyl ester
1-甲基-1H-吡唑-5-羧酸
3,5-Dichlorobenzoyl chloride
Lanthanum (III) chloride, anhydrous
4-[2-N,N-DIMETHYLETHOXY]PHENYLBROMIDE
1-(邻-甲苯基)哌嗪
4-methyl-2-pyridylzinc bromide solution
2-methylthieno[3,2-d]pyrimidin-4-ol
6-BroMo-5-fluoro-nicotinic acid Methyl ester
1-甲基-1H-吡唑-5-羧酸
3,5-Dichlorobenzoyl chloride
Lanthanum (III) chloride, anhydrous
4-[2-N,N-DIMETHYLETHOXY]PHENYLBROMIDE
1-(邻-甲苯基)哌嗪
4-methyl-2-pyridylzinc bromide solution