THYMINE-1-ACETIC ACID Chemical Properties

Melting point:

272-278 °C (dec.) (lit.)

Density 

1.416

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

3.81±0.10(Predicted)

color 

White

InChI

InChI=1S/C7H8N2O4/c1-4-2-9(3-5(10)11)7(13)8-6(4)12/h2H,3H2,1H3,(H,10,11)(H,8,12,13)

InChIKey

TZDMCKHDYUDRMB-UHFFFAOYSA-N

SMILES

C1(=O)N(CC(O)=O)C=C(C)C(=O)N1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

THYMINE-1-ACETIC ACID Usage And Synthesis

Synthesis

5-Methyluracil (10.0 g, 79.3 mmol) was suspended in distilled water (150 mL). Aqueous potassium hydroxide solution (50 mL, 3.6 M) was slowly added to the suspension. The mixture was stirred at room temperature for 10 minutes until the solution gradually became clear. Subsequently, chloroacetic acid (15.0 g, 159 mmol) was added to the clarified solution. The reaction mixture was heated to reflux and kept for 90 minutes. Upon completion of the reaction, the solution was cooled to room temperature and acidified with concentrated hydrochloric acid to pH=3. The acidified solution was placed in a refrigerator at 4°C overnight to promote the formation of white crystalline precipitate. The white crystalline precipitate was collected by filtration and dried under vacuum using phosphorus pentoxide (P2O5), resulting in 4.5 g of thymine-1-acetic acid in 31% yield.

References

[1] Chemistry - A European Journal, 2000, vol. 6, # 1, p. 62 - 72
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 2, p. 291 - 298
[3] Bioconjugate Chemistry, 2016, vol. 27, # 10, p. 2301 - 2306
[4] European Journal of Organic Chemistry, 2013, # 22, p. 4804 - 4815
[5] Patent: CN108478807, 2018, A. Location in patent: Paragraph 0022; 0053; 0070; 0071

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