| Identification | More | [Name]
6-Chloro-3-methyluracil | [CAS]
4318-56-3 | [Synonyms]
3-METHYL-6-CHLOROURACIL
6-CHLORO-3-METHYLURACIL
6-chloro-3-methyl-2,4(1H,3H)-pyrimidinedione
6-chloro-3-methylpyrimidine-2,4(1H,3H)-dione
6-Chloro-3-dimethyl uracil
3-METHYL-6-CHLOROURACI
6-Chloro-3-Methyuracil
3-Methyl-6-chlorouracil, GC 97%
6-CHLORO-3-METHYLURACIL, 98+%
6-Chloro-3-methyluracil ,99% | [EINECS(EC#)]
610-113-2 | [Molecular Formula]
C5H5ClN2O2 | [MDL Number]
MFCD01074837 | [Molecular Weight]
160.56 | [MOL File]
4318-56-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
278-280°C (dec.) | [density ]
0,896 gr/cm | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
7.16±0.40(Predicted) | [color ]
White to Almost white | [Detection Methods]
HPLC,NMR | [BRN ]
511456 | [InChI]
InChI=1S/C5H5ClN2O2/c1-8-4(9)2-3(6)7-5(8)10/h2H,1H3,(H,7,10) | [InChIKey]
SGLXGFAZAARYJY-UHFFFAOYSA-N | [SMILES]
C1(=O)NC(Cl)=CC(=O)N1C | [CAS DataBase Reference]
4318-56-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1992 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29335900 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
6-Chloro-3-methyluracil have been used in the synthesis of antibacterial agents as inhibitors of Helicobacter pylori glutamate racemase. | [Definition]
ChEBI: 6-Chloro-3-methyluracil is a member of pyrimidines and an organohalogen compound. | [Synthesis]
General procedure for the synthesis of 3-methyl-6-chlorouracil from 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione: Water (2.7 mL) was added slowly and dropwise at 0 °C to a 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mmol) formed with phosphorus oxychloride (POCl3, 95 mL) in a in a suspension. Subsequently, the reaction mixture was warmed to 80 °C and maintained for 5 hours. Upon completion of the reaction, the resulting brown solution was cooled and the POCl3 was evaporated under reduced pressure.The residue was treated with methanol (MeOH) and the resulting solid was purified by recrystallization from ethanol to give 11.5 g of 3-methyl-6-chlorouracil (yield: 71.6%). The melting point of the product was 279-282 °C (decomposition), which is consistent with literature values (280-282 °C).1H NMR (400 MHz, DMSO-d6) δ 3.10 (s, 3H), 5.90 (s, 1H), 12.4 (br s, 1H). | [References]
[1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 3, p. 594 - 597
[2] Tetrahedron Asymmetry, 1997, vol. 8, # 14, p. 2319 - 2323
[3] Patent: WO2009/73210, 2009, A1. Location in patent: Page/Page column 76
[4] Patent: WO2006/133261, 2006, A2. Location in patent: Page/Page column 30
[5] Patent: WO2007/143705, 2007, A2. Location in patent: Page/Page column 23 |
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