| Identification | Back Directory | [Name]
2(1H)-Pyrimidinone, hydrazone (9CI) | [CAS]
7504-94-1 | [Synonyms]
2-Pyrimidinylhydrazine
2-HydrazinylpyriMidine
1-(2-Pyrimidinyl)hydrazine
1-(Pyrimidine-2-yl)hydrazine
2(1H)-Pyrimidinone hydrazone
2-Hydrazono-2,3-dihydropyrimidine
2(1H)-Pyrimidinone, hydrazone (9CI)
2-hydrazinopyrimidine(SALTDATA: FREE) | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C4H6N4 | [MDL Number]
MFCD01249337 | [MOL File]
7504-94-1.mol | [Molecular Weight]
110.117 |
| Chemical Properties | Back Directory | [Melting point ]
86-88 °C(Solv: benzene (71-43-2)) | [Boiling point ]
246.3±23.0 °C(Predicted) | [density ]
1.39±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
solid | [pka]
6.17±0.20(Predicted) | [color ]
Off-white | [InChI]
InChI=1S/C4H6N4/c5-8-4-6-2-1-3-7-4/h1-3H,5H2,(H,6,7,8) | [InChIKey]
QDGHXQFTWKRQTG-UHFFFAOYSA-N | [SMILES]
C1(NN)=NC=CC=N1 | [CAS DataBase Reference]
7504-94-1 |
| Hazard Information | Back Directory | [Uses]
2-Hydrazinopyrimidine and other pyrimidinylhydrazones have been used to study the fungicidal activity of heteroaromatic aldehyde and ketone pyrimidinylhydrazones. | [Synthesis]
The general procedure for the synthesis of 2-hydrazinopyrimidine from 2-chloropyrimidine was as follows: first, 2-chloropyrimidine (1.145 g, 20 mmol) was dissolved in ethanol (30 mL). Subsequently, an excess of 85% hydrazine hydrate (6 mL) was slowly added to the above solution under continuous stirring. The reaction mixture gradually changed to a bright yellow solution and white needle-like crystals were precipitated after 2 hours. The crystals were collected by filtration and recrystallized in ethanol to afford the target product 2-hydrazinopyrimidine in 80% yield. Next, 3-methylsalicylaldehyde (1.36 g, 10 mmol) was added to an ethanolic solution (30 mL) of 2-hydrazinopyrimidine (1.10 g, 10 mmol) and the formation of a pale yellow precipitate was immediately observed. After refluxing the reaction mixture for 3 h, the precipitate was filtered and collected and washed with ethanol to give a final light yellow H2mphp powder in 95% yield. | [References]
[1] Patent: WO2018/64119, 2018, A1. Location in patent: Paragraph 1484
[2] Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5644 - 5649
[3] Patent: US2003/187014, 2003, A1
[4] Journal of Coordination Chemistry, 2016, vol. 69, # 7, p. 1218 - 1225
[5] Journal of Physical Organic Chemistry, 2015, vol. 28, # 2, p. 108 - 115 |
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