| Identification | Back Directory | [Name]
6-CHLORO-5-NITROPYRIMIDIN-4-AMINE | [CAS]
4316-94-3 | [Synonyms]
NSC 401941
AKOS A0602-0633
AKOS BBS-00002074
IFLAB-BB F1386-0156
6-Chloro-5-nitro-4-pyrimidinamine
6-CHLORO-5-NITROPYRIMIDIN-4-AMINE
4-AMino-5-nitro-6-chloropyriMidine
4-Amino-6-chloro-5-nitropyrimidine
4-Chloro-5-nitro-6-pyrimidinylamine
4-PyriMidinaMine, 6-chloro-5-nitro-
(6-chloro-5-nitro-pyrimidin-4-yl)amine | [Molecular Formula]
C4H3ClN4O2 | [MDL Number]
MFCD00127772 | [MOL File]
4316-94-3.mol | [Molecular Weight]
174.55 |
| Chemical Properties | Back Directory | [Melting point ]
155-156 °C | [Boiling point ]
394.7±37.0 °C(Predicted) | [density ]
1.712±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
-1.07±0.10(Predicted) | [Appearance]
Off-white to light yellow Solid | [InChI]
InChI=1S/C4H3ClN4O2/c5-3-2(9(10)11)4(6)8-1-7-3/h1H,(H2,6,7,8) | [InChIKey]
BWLOHIMQWHFSQF-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=C([N+]([O-])=O)C(N)=N1 |
| Hazard Information | Back Directory | [Uses]
6-Chloro-5-nitropyrimidin-4-amine is a substituted pyrimidine with antifungal properties. | [Synthesis]
4,6-Dichloro-5-nitropyrimidine (9.7 g, 50 mmol) was used as starting material and dissolved in tetrahydrofuran (100 mL). To this solution ammonia (100 mL) and sodium bicarbonate (4.6 g, 55 mmol) were added sequentially. The reaction mixture was heated to 55°C and stirred at this temperature overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the organic solvent was subsequently evaporated under reduced pressure. The residue was filtered and purified by fast column chromatography (eluent ratio of dichloromethane: methanol = 100:1) to give the final target product 4-amino-6-chloro-5-nitropyrimidine (6-chloro-5-nitropyrimidin-4-amine, 8.1 g, 93% yield). | [References]
[1] Patent: CN106146504, 2016, A. Location in patent: Paragraph 0136; 0137; 0138; 0139; 0140
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1314,1315
[3] Journal of the Chemical Society, 1951, p. 96,99
[4] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 371,376,377
[5] Tetrahedron, 2002, vol. 58, # 38, p. 7607 - 7611 |
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SynAsst Chemical.
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021-60343070 |
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