6-PHENYL-2-THIOURACIL Chemical Properties

Melting point:

263-264.5 °C(Solv: water (7732-18-5))

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Aqueous Base (Slightly), DMSO (Slightly)

form 

Solid

pka

7.29±0.20(Predicted)

color 

White to Off-White

biological source

synthetic (organic)

CAS DataBase Reference

36822-11-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

6-PHENYL-2-THIOURACIL Usage And Synthesis

Chemical Properties

White powder

Uses

6-Phenyl-2-thiouracil is a thyreostatic (thyroid hormone) agent that may be used as a reference material in thyreostatic drug separation and detection technologies such as capillary electrophoresis, HPLC, or gas chromatography.

Definition

ChEBI: 6-Phenyl-2-thiouracil is a member of pyrimidines.

Synthesis

To a solution of ethyl benzoylacetate (2 g, 10.41 mmol) in ethanol (15 mL) was added sodium ethoxide (7 mL, 18.7 mmol) and compound (CAS:17356-08-0) (1.18 g, 15.61 mmol). The reaction mixture was stirred under reflux conditions overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in water, the pH was adjusted to 3 with acid and extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by fast column chromatography using dichloromethane/methanol (2.5%) as eluent to afford 2-mercapto-6-phenyl-4-hydroxypyrimidine (500 mg, 2.44 mmol) as a white solid in 24% yield.

References

[1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999, vol. 54, # 6, p. 788 - 798
[2] Synthetic Communications, 2002, vol. 32, # 6, p. 851 - 855
[3] Patent: WO2016/30534, 2016, A1. Location in patent: Page/Page column 109
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 745 - 759
[5] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 203

6-PHENYL-2-THIOURACIL(36822-11-4)Related Product Information

• 6-PHENYL-2-THIOURACIL
• 4-Phenylpyrimidine
• Uracil
• 2-Thiouracil
• 3-(4-OXO-6-PHENYL-1,4-DIHYDRO-PYRIMIDIN-2-YLSULFANYL)-PROPIONIC ACID
• 2-[(2-CHLOROBENZYL)SULFANYL]-4-HYDROXY-6-PHENYL-5-PYRIMIDINECARBONITRILE
• (4-OXO-6-PHENYL-1,4-DIHYDRO-PYRIMIDIN-2-YL-SULFANYL)-ACETIC ACID
• BUTTPARK 14\02-43
• N-(2,6-DIMETHYLPHENYL)-2-[(4-OXO-6-PHENYL-1,4-DIHYDROPYRIMIDIN-2-YL)THIO]ACETAMIDE
• BUTTPARK 14\02-47
• 4-HYDROXY-6-PHENYL-2-([3-(TRIFLUOROMETHYL)BENZYL]SULFANYL)-5-PYRIMIDINECARBONITRILE
• 2-[(2-PHENOXYETHYL)THIO]-6-PHENYLPYRIMIDIN-4(1H)-ONE
• BUTTPARK 13\01-50
• BUTTPARK 14\02-41
• BUTTPARK 17\09-58
• 4-HYDROXY-2-(METHYLSULFANYL)-6-PHENYL-5-PYRIMIDINECARBONITRILE
• 4-HYDROXY-2-(METHYLTHIO)-6-PHENYLPYRIMIDINE
• BUTTPARK 14\02-45