| Identification | More | [Name]
6-(Chloromethyl)uracil | [CAS]
18592-13-7 | [Synonyms]
5-CHLORO-6-METHYLURACIL
6-(CHLOROMETHYL)PYRIMIDINE-2,4(1H,3H)-DIONE
6-(CHLOROMETHYL)URACIL
TIMTEC-BB SBB003961
3h)-pyrimidinedione,6-(chloromethyl)-4(1h
6-methyl-5-chlorouracil
5-CHLORO-6-METHYL-DIHYDRO-PYRIMIDINE-2,4-DIONE
6-(Chloromethyl)uracil 98%
4-(chloromethyl)uracil
6-Chloromethyl-1H-pyrimidine-2,4-dione | [EINECS(EC#)]
242-431-9 | [Molecular Formula]
C5H5ClN2O2 | [MDL Number]
MFCD00466419 | [Molecular Weight]
160.56 | [MOL File]
18592-13-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
257 °C (dec.)(lit.)
| [density ]
1.393±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
almost transparency in N,N-DMF | [form ]
powder to crystal | [pka]
7.91±0.10(Predicted) | [color ]
White to Light yellow | [InChI]
InChI=1S/C5H5ClN2O2/c6-2-3-1-4(9)8-5(10)7-3/h1H,2H2,(H2,7,8,9,10) | [InChIKey]
VCFXBAPEXBTNEA-UHFFFAOYSA-N | [SMILES]
C1(=O)NC(CCl)=CC(=O)N1 | [CAS DataBase Reference]
18592-13-7(CAS DataBase Reference) | [EPA Substance Registry System]
18592-13-7(EPA Substance) |
| 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 . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
6-(Chloromethyl)uracil is an alkali-resistant protein adsorbent, suitable for medical procedures. it is also used in the synthesis of chlorophenyl hydroxypiperidine analogs having anti-amylatic activity. | [Synthesis]
In a 250 mL three-necked flask, 6-(hydroxymethyl)uracil (11.5 g, 0.081 mol) was added, followed by 115 mL of dichloromethane, thionyl chloride (17.6 mL, 0.24 mol) and a catalytic amount of N,N-dimethylformamide in sequence. The reaction mixture was heated to reflux temperature and stirred continuously for 2 hours. After completion of the reaction, it was cooled to room temperature, the solid product was collected by filtration, washed with dichloromethane and dried to give 6-(chloromethyl)uracil (11.8 g, 90.8% yield). | [References]
[1] European Journal of Medicinal Chemistry, 2013, vol. 70, p. 400 - 410
[2] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 367 - 373
[3] Patent: CN106831607, 2017, A. Location in patent: Paragraph 0049
[4] Patent: CN106892902, 2017, A. Location in patent: Paragraph 0099; 0100; 0101; 0102 |
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