6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione Chemical Properties

Melting point:

109-113 °C

Boiling point:

224.6±50.0 °C(Predicted)

Density 

1.4926 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

-3.53±0.40(Predicted)

color 

Pale Yellow

Water Solubility 

soluble

BRN 

144393

InChI

InChI=1S/C6H7ClN2O2/c1-8-4(7)3-5(10)9(2)6(8)11/h3H,1-2H3

InChIKey

VATQPUHLFQHDBD-UHFFFAOYSA-N

SMILES

C1(=O)N(C)C(Cl)=CC(=O)N1C

CAS DataBase Reference

6972-27-6(CAS DataBase Reference)

NIST Chemistry Reference

6-Chloro-2,4-dihydroxy-1,3-dimethylpyrimidine(6972-27-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione Usage And Synthesis

Chemical Properties

white to light yellow flakes or powder

Uses

6-Chloro-1,3-dimethyluracil is a nucleobase constitute of nucleic acid. An intermediate for the synthesis of substituted uracils and derivatives.

Synthesis

1,3-Dimethylbarbituric acid (compound SM1) (7 kg, 44.9 mmol) was used as raw material and dissolved in 120 kg of phosphoryl chloride (POCl3). Water (2.2 kg, 122 mol) was slowly added dropwise to the above solution. After the dropwise addition, the reaction was slowly heated to reflux and maintained for 6 hours; the reaction process was monitored by high performance liquid chromatography (HPLC). Upon completion of the reaction, the reaction solution was slowly poured into a large volume of ice water (100 L) and subsequently extracted twice with dichloromethane (50 L) to combine the organic phases. The organic phase was washed with saturated brine (20 L), dried over anhydrous sodium sulfate, filtered and concentrated the organic phase, and finally the yellow solid product 6-chloro-1,3-dimethyluracil (compound SM2) (7.2 kg) was obtained by vacuum drying in 92.3% yield.

References

[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 6, p. 690 - 697
[2] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 6, p. 836 - 844
[3] Patent: CN103755705, 2017, B. Location in patent: Paragraph 0033; 0034; 0035
[4] Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 158,162
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 10, p. 869 - 871

6-Chloro-1,3-dimethyl-2,4-(1H,3H)-pyrimidinedione(6972-27-6)Related Product Information

• 3-[4-(2-methoxyphenyl)-1-piperazinyl]propanenitrile
• 1-(2-Methoxyphenyl)piperazine
• 6-[(3-chloropropyl)amino]-1,3-dimethyluracil
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• ZEBULARINE
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• N-METHYLBARBITURIC ACID
• 4-Fluoro-2-methylbenzonitrile
• 2-(Bromomethyl)-6-fluorobenzonitrile