6-Aminothiouracil Chemical Properties

Melting point:

>300?C (dec.)

Boiling point:

246.5°C

Density 

1.397 (estimate)

refractive index 

1.7490 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

crystalline solid

pka

7.92±0.20(Predicted)

color 

Off-white

Water Solubility 

256.3mg/L(25 ºC)

InChI

InChI=1S/C4H5N3OS/c5-2-1-3(8)7-4(9)6-2/h1H,(H4,5,6,7,8,9)

InChIKey

YFYYRKDBDBILSD-UHFFFAOYSA-N

SMILES

C1(=S)NC(N)=CC(=O)N1

CAS DataBase Reference

1004-40-6(CAS DataBase Reference)

NIST Chemistry Reference

Uracil, 6-amino-2-thio-(1004-40-6)

EPA Substance Registry System

6-Amino-2-thiouracil (1004-40-6)

Safety Information

Hazard Codes 

Xi

RTECS 

UW0495000

HS Code 

2933599590

Toxicity

LD50 ipr-mus: 370 mg/kg ARZNAD 31,1713,81

6-Aminothiouracil Usage And Synthesis

Chemical Properties

White Solid

Uses

LAbelled derivative of 6-Amino-2-thiouracil as novel, potent, and selective A3 adenosine receptor antagonists.

Safety Profile

Poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx and SOx.

Synthesis

General procedure for the synthesis of 6-amino-2-thiouracil from the compound (CAS: 17356-08-0) and ethyl cyanoacetate: 101.5 g (1.88 mol) of sodium methanol was accurately weighed in a reaction flask containing 3 L of 670 g ethanol at room temperature. Subsequently, 67.3 g (0.88 mol) of thiourea was added and stirred until complete dissolution. The reaction mixture was heated to 55 °C and then 100 g (0.884 mol) of ethyl cyanoacetate was slowly added. The heating was continued to reflux and the reflux reaction was maintained for 4.5 h. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction solution was cooled to 15 °C. The reaction mixture was filtered and the filter cake was washed once with 170 g ethanol. The washed filter cake was transferred to a 3 L reaction flask and appropriate amount of water was added, followed by 1.3 kg of water and stirred until complete dissolution. The pH of the solution was adjusted to 4 by slowly adding acetic acid at 20 °C, at which point a large amount of solid precipitated. The solid product was collected by filtration using a suction filter. The filter cake was dried at 45 °C overnight to give a final product of 115.4 g of 6-amino-2-thiouracil in 91.7% yield.

References

[1] Patent: CN106008633, 2016, A. Location in patent: Paragraph 0065; 0066; 0067; 0068
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 662 - 668
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4612 - 4621
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 18, p. 3389 - 3395
[5] Australian Journal of Chemistry, 2007, vol. 60, # 2, p. 120 - 123

6-Aminothiouracil(1004-40-6)Related Product Information

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• 6-Mercaptopurine
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• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• 1-PHENYL-2-THIOUREA
• POTASSIUM THIOGLYCOLATE
• 4-Hydroxy-6-aminopyrimidine
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane