2,4-Dichloro-6-methyl-5-nitropyrimidine Chemical Properties

Melting point:

52-54°C

Boiling point:

135-136 °C(Press: 22 Torr)

Density 

1.626±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-5.30±0.39(Predicted)

form 

Solid

color 

Pale Yellow to Light Beige

Stability:

Moisture Sensitive

InChI

InChI=1S/C5H3Cl2N3O2/c1-2-3(10(11)12)4(6)9-5(7)8-2/h1H3

InChIKey

NBCOZXBHPKSFSA-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(C)=C([N+]([O-])=O)C(Cl)=N1

CAS DataBase Reference

13162-26-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41-36/37/38

Safety Statements 

26-39-36/37/39

HS Code 

29335990

2,4-Dichloro-6-methyl-5-nitropyrimidine Usage And Synthesis

Chemical Properties

Yellow Crystalline Solid

Uses

A synthetic intermediate

Synthesis

General procedure for the synthesis of 2,4-dichloro-5-nitro-6-methylpyrimidine from 2,4-dihydroxy-6-methyl-5-nitropyrimidine: 2,4-dihydroxy-6-methyl-5-nitropyrimidine (1 eq.) was dissolved in 17.54 mL of phosphoryl chloride, and 2.92 mL of N,N-dimethylaniline (1 eq.) was slowly added dropwise at room temperature. Subsequently, 8.04 μL of DMF (0.00445 eq.) was slowly added under reflux conditions and the reaction lasted for 8 hours. Upon completion of the reaction, the trichlorophosphorus oxide was removed by distillation under reduced pressure. Ice water was added to the residue and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation to give a light yellow to brown oil. The oily substance was purified by column chromatographic separation to give a final yellow solid 2,4-dichloro-5-nitro-6-methylpyrimidine (1 g) in 65% yield.

References

[1] Patent: CN105906621, 2016, A. Location in patent: Paragraph 0031
[2] Bulletin de la Societe Chimique de France, 1951, p. 428
[3] Helvetica Chimica Acta, 1951, vol. 34, p. 835,837
[4] Journal of the Chemical Society, 1951, p. 1004,1015
[5] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84

2,4-Dichloro-6-methyl-5-nitropyrimidine(13162-26-0)Related Product Information

• 4,6-Dichloro-5-nitropyrimidine
• Methyl acetate
• Dichlorodimethylsilane
• 2,4-Dichloro-5-methylpyrimidine
• 2,4-Dichloro-5-nitropyrimidine
• 2-Chloro-5-chloromethylpyridine
• METSULFURON METHYL
• Methyl salicylate
• Dichloromethylphenylsilane
• 1,3-Dichloro-5,5-dimethylhydantoin
• 2,4-Dichloropyrimidine
• 1,1-Dichlorodimethyl ether
• Tribenuron methyl
• Dichloroacetic acid
• Pirimiphos-methyl
• Kresoxim-methyl
• Thiophanate-methyl
• Methyl