Methylthiouracil

Base Information

• Chemical Name: Methylthiouracil
• CAS No.: 56-04-2
• Deprecated CAS: 1123-10-0,31909-18-9,91795-77-6,31909-18-9,91795-77-6
• Molecular Formula: C5H6N2OS
• Molecular Weight: 142.181
• Hs Code.: 29335995
• European Community (EC) Number: 200-252-3
• NSC Number: 757116,193526,9378
• UN Number: 3077
• UNII: QW24888U5F
• DSSTox Substance ID: DTXSID2020890
• Nikkaji Number: J4.566G
• Wikipedia: Methylthiouracil
• Wikidata: Q6824062
• NCI Thesaurus Code: C81590
• Metabolomics Workbench ID: 78640
• ChEMBL ID: CHEMBL1330588
• Mol file: 56-04-2.mol

Synonyms:4-Methyl-2-thiouracil;Alkiron;Metacil;Methylthiouracil;Thimecil

Chemical Property of Methylthiouracil

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.83E-05mmHg at 25°C
• Melting Point: ~330 °C (dec.)(lit.)
• Refractive Index: 1.638
• Boiling Point: 342.3 °C at 760 mmHg
• PKA: pKa 8.2 (Uncertain)
• Flash Point: 160.8 °C
• PSA: 80.74000
• Density: 1.36 g/cm³
• LogP: 0.74090
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Heated), Methanol (Slightly, Heated)
• Water Solubility.: INSOLUBLE
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.02008399
• Heavy Atom Count: 9
• Complexity: 197
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

6-?Methyl-?2-?thiouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-40
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)NC(=S)N1
• Uses: antithyroid agent 6-?Methyl-?2-?thiouracil is a derivative of methylthiouracil (M330710), a competitive inhibitor of Nitric Oxide Synthase (NOS). Potential anti-inflammatory agent.

Technology Process of Methylthiouracil

There total 26 articles about Methylthiouracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.7%

ethyl acetoacetate (141-97-9) + thiourea (17356-08-0) → 6-methyl-2-thiouracil (56-04-2)

Guidance literature:

With potassium hydroxide; In ethanol; at 85 ℃; for 3h;

DOI:10.1016/j.bmcl.2014.04.037

Reference yield: 94.6%

ethyl acetoacetate (141-97-9) + thiourea (17356-08-0) → 6-methyl-2-thiouracil (56-04-2,91795-77-6)

Guidance literature:

With potassium hydroxide; In ethanol; at 125 ℃; for 0.416667h; under 15514.9 Torr; Microwave irradiation; Inert atmosphere;

DOI:10.1021/op900287j

Reference yield: 70.0%

5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione (72324-39-1) + thiourea (17356-08-0) → 6-methyl-2-thiouracil (56-04-2,91795-77-6)

Guidance literature:

5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione; With alcohol; Microwave irradiation;

thiourea; for 0.05h; Microwave irradiation;

upstream raw materials:

4-methyleneoxetan-2-one

thiourea

sodium methylate

ethyl acetoacetate

Downstream raw materials:

C-5-Piperidinomethylene-6-methyl-2-thiouracil

2-(4-chloro-phenylsulfanyl)-6-methyl-3H-pyrimidin-4-one

6-Methyluracil

2-para-nitro-benzylthio-6-methyluracil

Refernces

• 1、 Wang, Shi-Chun,Gao, Ji-Gang,Zhang, Shuai,Liu, Si,Jiang, Lin. "Synthesis of novel pyrimidine derivatives with (pyridin-3-ylmethyl)thio and phenylamino moieties and evaluation of their antifungal activity". . p. 245 - 248. Retrieved 2018.
• 2、 -. "NOVEL ANTIPARASITIC COMPOUNDS AND METHODS". Page/Page column 92. . Retrieved 2021/04/23.
• 3、 Hao, Shulin,Cai, Zengfei,Cao, Yangyang,Du, Xiaohua. "Design, synthesis, and acaricidal activity of phenyl methoxyacrylates containing 2-alkenylthiopyrimidine". . . Retrieved 2020/09/16.