4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE Chemical Properties

Melting point:

103-105°C

Boiling point:

367.3±37.0 °C(Predicted)

Density 

1.58±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Ethyl Acetate

form 

Solid

pka

-7.56±0.39(Predicted)

color 

Light Yellow

InChI

InChI=1S/C6H3Cl2N3S/c1-12-6-10-4(7)3(2-9)5(8)11-6/h1H3

InChIKey

GLOOTGZVAHKTJS-UHFFFAOYSA-N

SMILES

C1(SC)=NC(Cl)=C(C#N)C(Cl)=N1

Safety Information

Hazard Codes 

T,C

Risk Statements 

25-34

Safety Statements 

26-36/37/39-45

RIDADR 

2923

WGK Germany 

3

PackingGroup 

Ⅲ

HS Code 

2933599590

4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile (cas# 33097-13-1) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 2-methylthio-4,6-dichloropyrimidine-5-oxime from 2-methylthio-4,6-dichloro-5-cyanopyrimidine: To 4,6-dichloro-2-(methylthio)-5-pyrimidine carboxaldehyde oxime (2.38 g, 10 mmol) was slowly added dichlorosulfoxide (SOCl2, 21.8 mL, 0.30 mol) at room temperature. Subsequently, the reaction mixture was heated to 75 °C with continuous stirring for about 3 hours. After completion of the reaction, the reaction solution was concentrated under vacuum. The residual dichlorosulfoxide was removed by addition of toluene (5 mL) and evaporated under vacuum. The resulting solid was washed with ethanol/water (10 mL, 1:1 v/v) to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbonitrile (2.04 g, 93% yield). The product was analyzed by LC-MS showing m/z 220 ([M+H]+) with a retention time of 1.99 min; 1H-NMR (CDCl3) δ 2.64 (3H, s).

References

[1] Patent: WO2006/104917, 2006, A2. Location in patent: Page/Page column 81-82
[2] Tetrahedron Letters, 2009, vol. 50, # 3, p. 370 - 372
[3] Patent: WO2006/104889, 2006, A2. Location in patent: Page/Page column 114
[4] Patent: WO2007/147109, 2007, A2. Location in patent: Page/Page column 101-102
[5] Patent: WO2007/84560, 2007, A2. Location in patent: Page/Page column 111

4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE(33097-13-1)Related Product Information

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• 4,6-DIBROMOPYRIMIDINE
• 4,6-DIBROMOQUINOLINE
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• 4,6-DICHLORO-2-METHYLQUINAZOLINE
• 4,6-DICHLORO-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• 4,6-DICHLOROQUINOLINE
• 4,6-DICHLOROPYRIDO[3,4-D]PYRIMIDINE
• ETHYL 4,6-DICHLORO-3-QUINOLINECARBOXYLATE
• 4,6-Dichloro-2-(methylthio)pyrimidine
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE
• 2-METHYLSULFANYL-PYRIMIDINE-5-CARBONITRILE
• 4,6-Dichloro-5-methylpyrimidine
• 4-Chloro-2-(methylthio)pyrimidine-5-carbonitrile ,97%
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• 4-CHLORO-5-METHYL-2-METHYLSULFANYL-PYRIMIDINE
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• 4,6-dichloropyrimidine-5-carbonitrile