2(1H)-Pyrimidinone, hydrazone (9CI) Chemical Properties

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

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

29339900

2(1H)-Pyrimidinone, hydrazone (9CI) Usage And Synthesis

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

2(1H)-Pyrimidinone, hydrazone (9CI)(7504-94-1)Related Product Information

• 2-Hydrazino-4-(trifluoromethyl)pyrimidine
• 2-Hydrazino-4,6-dimethylpyrimidine
• 2,4(1H,3H)-Pyrimidinedione, 6-methyl-, 2-hydrazone (9CI)
• Binodenoson
• 5-(4-CHLOROBENZYLOXYCARBONYL)-4-(TRIFLUOROMETHYL)PYRIMIDIN-2-YL HYDRAZINE
• CHEMBRDG-BB 4021967
• 5-(METHOXYCARBONYL)-4-(TRIFLUOROMETHYL)PYRIMIDINE-2-HYDRAZINE
• 2,4-DIHYDRAZINOPYRIMIDINE
• METHYL 2-[2-(2,3,3-TRICHLOROACRYLOYL)HYDRAZINO]-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 4-CHLOROBENZYL 2-[2-(2,3,3-TRICHLOROACRYLOYL)HYDRAZINO]-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 2,4-DIHYDRAZINO-5-NITRO-6-METHYLPYRIMIDINE
• 2,4-DIHYDRAZINO-5-NITROPYRIMIDINE
• 4-CHLOROBENZYL 2-[2-(2-CHLOROACETYL)HYDRAZINO]-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 2-(CINNAMYLIDENEHYDRAZINO)-4-HYDROXY-6-METHYLPYRIMIDINE
• 2-HYDRAZINO-4,6-DIPHENYL-PYRIMIDINE
• N'-(4-HYDROXY-6-METHYLPYRIMIDIN-2-YL)ACETOHYDRAZIDE
• 4-(DIMETHYLAMINO)BENZALDEHYDE (4,6-DIMETHYLPYRIMIDIN-2-YL)HYDRAZONE
• ETHYL 2-OXO-2-(2-[4-(TRIFLUOROMETHYL)PYRIMIDIN-2-YL]HYDRAZINO)ACETATE