Methylthiouracil CAS 56-04-2
Introduction：Basic information about Methylthiouracil CAS 56-04-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Methylthiouracil Basic information
| Product Name: | Methylthiouracil |
| Synonyms: | LABOTEST-BB LT00848091;AURORA KA-4696;METHIOCIL;METHYLTHIOURACIL;4-OXO-2-MERCAPTO-6-METHYLPYRIMIDINE;4-HYDROXY-2-MERCAPTO-6-METHYLPYRIMIDINE;4-HYDROXY-6-METHYL-2-THIOPYRIMIDINE;4-METHYL-2-THIOURACIL |
| CAS: | 56-04-2 |
| MF: | C5H6N2OS |
| MW: | 142.18 |
| EINECS: | 200-252-3 |
| Product Categories: | alcohol|sulfide;PYRIMIDINE;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines;1;56-04-2 |
| Mol File: | 56-04-2.mol |
Methylthiouracil Chemical Properties
| Melting point | ~330 °C (dec.)(lit.) |
| density | 1.291 (estimate) |
| refractive index | 1.6430 (estimate) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | DMSO (Heated), Methanol (Slightly, Heated) |
| pka | pKa 8.2 (Uncertain) |
| form | Liquid |
| color | Clear colorless to yellow |
| Water Solubility | INSOLUBLE |
| Merck | 14,6128 |
| BRN | 115648 |
| Stability: | Incompatible with strong oxidizing agents, iodine, metals. |
| InChI | 1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9) |
| InChIKey | HWGBHCRJGXAGEU-UHFFFAOYSA-N |
| SMILES | CC1=CC(=O)NC(=S)N1 |
| CAS DataBase Reference | 56-04-2(CAS DataBase Reference) |
| IARC | 2B (Vol. Sup 7, 79) 2001 |
| NIST Chemistry Reference | 6-Methyl-2-thiouracil(56-04-2) |
| EPA Substance Registry System | Methylthiouracil (56-04-2) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-40 |
| Safety Statements | 36/37-45 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | YR0875000 |
| Hazard Note | Irritant/Possible Carcinogen |
| TSCA | TSCA listed |
| HazardClass | 9 |
| HS Code | 29335995 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Skin Sens. 1 |
| Hazardous Substances Data | 56-04-2(Hazardous Substances Data) |
| Toxicity | MLD in rabbits (mg/kg): 2486 orally (Simon) |
| Chemical Properties | white powder |
| Uses | antithyroid agent |
| Uses | 6-?Methyl-?2-?thiouracil is a derivative of methylthiouracil (M330710), a competitive inhibitor of Nitric Oxide Synthase (NOS). Potential anti-inflammatory agent. |
| Definition | ChEBI: Methylthiouracil is a pyrimidone. |
| General Description | White crystalline powder with an odor of onions and a bitter taste. A saturated aqueous solution is neutral or slightly acidic. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Methylthiouracil reacts with strong oxidizing agents. Forms complexes with metals and is oxidized by iodine and other sulfhydryl oxidizing agents . |
| Fire Hazard | Flash point data for Methylthiouracil are not available. Methylthiouracil is probably combustible. |
| Safety Profile | Confirmed carcinogenwith experimental carcinogenic,neoplastigenic, tumorigenic, and teratogenicdata. Poison by intraperitoneal route.Moderately toxic by ingestion. Humanteratogenic and reproductive effects by anunspecified route: developmentalabnormalities of the endocrine system andeffects on newborn including neonatalmeasures or effects. Experimentalreproductive effects. Used to treathyperthyroidism. When heated todecomposition it emits very toxic fumes ofNOx and SOx. |
| Synthesis | 141-97-9 17356-08-0 56-04-2 Sodium metal (30 mmol) was added to methanol (10 mL) and after complete dissolution, thiourea (10 mmol) and ethyl acetoacetate (10 mmol) were added sequentially. The reaction mixture was heated to reflux for 7 hours. After completion of the reaction, methanol was removed by distillation under reduced pressure and the residue was dissolved in an appropriate amount of water and the pH was adjusted to neutral with acetic acid. The precipitate was collected by filtration to give the pale yellow crystalline product methylthiouracil (1.26 g, 90% yield). The product was characterized as follows: melting point 275-277°C; 1H NMR (δ, ppm): 2.09 (s, 3H, 6-CH3), 5.52 (s, 1H, CH-pyrimidine), 11.98 [b.s, 2H, (NH)2]; 13C NMR (δ, ppm): 17.88, 103.38, 151.91, 160.32, 175.83. 175.83. Elemental analysis results (C5H6N2OS) calculated values: C, 42.24; H, 4.25; N, 19.70; S, 22.55; measured values: C, 42.24; H, 4.25; N, 19.70; S, 22.55. |
| Purification Methods | Crystallise the thiouracil from a large volume of H2O. Purify it further by dissolving in base, adding charcoal, filtering and acidifying with AcOH. Suspend the wet solid (ca 100g) in boiling H2O (1L), stir and add AcOH (20mL), stir and refrigerate. Collect the product, wash it with cold H2O (4 x 200mL), drain it for several hours then place it in an oven at 70o to constant weight. [IR: Short & Thompson J Chem Soc 168 1952, Foster & Snyder Org Synth Coll Vol IV 638 1063, Beilstein 24 III/IV 1289.] |
| References | [1] Organic Process Research and Development, 2010, vol. 14, # 1, p. 205 - 214 [2] Journal of Chemistry, 2017, vol. 2017, [3] RSC Advances, 2017, vol. 7, # 28, p. 17427 - 17441 [4] Synthetic Communications, 2002, vol. 32, # 6, p. 851 - 855 [5] Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 6, p. 893 - 899 |
Methylthiouracil Preparation Products And Raw materials
| Raw materials | Sodium carbonate-->Sodium oxide-->Ethyl acetoacetate-->Carbamimidothioic acid-->Methanol-->Sodium formate |
| Preparation Products | 4-Hydroxy-6-methylpyrimidine-->6-Methyluracil-->6-Methyl-2-(methylthio)pyrimidin-4-ol-->Acetonitrile, 2-[[4-[(4-methoxyphenyl)amino]-6-methyl-2-pyrimidinyl]thio]--->4(1H)-Pyrimidinone, 6-methyl-2-[(phenylmethyl)thio]- |
