| Identification | More | [Name]
6-Chlorouracil | [CAS]
4270-27-3 | [Synonyms]
4-CHLORO-2,6-DIHYDROXYPYRIMIDINE
4-CHLOROURACIL
6-CHLORO-2,4(1H,3H)-PYRIMIDINEDIONE
6-CHLORO-2,4-DIHYDROXYPYRIMIDINE
6-CHLOROURACIL
AURORA KA-4918
SPECS AB-323/25048125
TIMTEC-BB SBB004104
2,4(1H,3H)-Pyrimidinedione, 6-chloro-
2,4-Pyrimidinediol,6-chloro-
6-Chloro-2,4-dihydroxypyrimidine~4-Chlorouracil
2,4(1H,3H)-Pyrimidinedione, 6-chloro-(9CI)
6-Chlorouracil,98+%
4-Chloro-2,6-dihydroxypyrimidine, 6-Chloro-2,4-dihydroxypyrimidine, 6-Chlorouracil | [EINECS(EC#)]
224-258-0 | [Molecular Formula]
C4H3ClN2O2 | [MDL Number]
MFCD00014595 | [Molecular Weight]
146.53 | [MOL File]
4270-27-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
290-295°C | [Boiling point ]
300°C | [density ]
1.61±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in Ammonium Hydroxide | [form ]
Solid | [pka]
6.24±0.10(Predicted) | [color ]
White | [Water Solubility ]
4.885g/L(25 ºC) | [BRN ]
120492 | [InChI]
InChI=1S/C4H3ClN2O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H2,6,7,8,9) | [InChIKey]
PKUFNWPSFCOSLU-UHFFFAOYSA-N | [SMILES]
C1(=O)NC(Cl)=CC(=O)N1 | [CAS DataBase Reference]
4270-27-3(CAS DataBase Reference) | [NIST Chemistry Reference]
6-Chlorouracil(4270-27-3) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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 | [HazardClass ]
IRRITANT | [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
6-Chlorouracil acts as an inhibitor of yeast alcohol dehydrogenase (ADH-H). 6-Chlorouracil is a potential inhibitor of DNA repair glycosylases. | [Uses]
Chlorouracil (4-Chlorouracil; 6-Chlorouracil) is a halogenated uracil that is useful in studies of the effects of halogenation on nucleic acid base-pair stability and alkali metal ion affinity. Reaction of 6-chlorouracil with 4-(dimethylamino)pyridine, 4-methylpyridine, and pyridin-4-yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross-conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray single crystal analyses may be used to characterize these systems and to compare the salts with the betaines. | [Synthesis]
General procedure for the synthesis of 6-chloropyrimidine-2,4(1H,3H)-dione from 2,4,6-trichloropyrimidine: 2,4,6-trichloropyrimidine (10.21 g, 0.56 mol) was dissolved in an aqueous solution (100 mL) containing NaOH (8.9 g, 0.22 mol), which was stirred under refluxing conditions for 1 hour. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 2-3 with concentrated hydrochloric acid. the mixture was placed in a refrigerator overnight to promote crystallization. Subsequently, the precipitate was collected by filtration, washed with cold water and dried under vacuum in the presence of phosphorus pentoxide. 6.43 g (0.54 mol, 97% yield) of 6-chlorouracil was finally obtained as a white crystalline solid. The spectral data of the product were in agreement with those reported in the literature [28] and [40]. Melting point > 280°C. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.00 (broad peak, 1H, NH), 11.09 (broad peak, 1H, NH), 5.66 (single peak, 1H, CH). IR (KBr, ν cm-1): 3095 (N-H stretching vibration), 1729,1709,1652 (C=O stretching vibration), 1616 (C=C stretching vibration), 1380 (C-N stretching vibration), 841 (N-H out-of-plane bending vibration), 790 (C-Cl stretching vibration). | [References]
[1] European Journal of Organic Chemistry, 2008, # 32, p. 5401 - 5406
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6352 - 6370
[3] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 159 - 174
[4] Organic Letters, 2018, vol. 20, # 2, p. 473 - 476
[5] Heterocycles, 1990, vol. 31, # 9, p. 1641 - 1646 |
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