1-(4-AMino-phenyl)-3-(4-tert-butyl-benzoyl)-thiourea

1-(4-AMino-phenyl)-3-(4-tert-butyl-benzoyl)-thiourea Property

storage temp. 

Store at -20°C

solubility 

insoluble in H2O; ≥14.45 mg/mL in DMSO; ≥2.88 mg/mL in EtOH with gentle warming

form 

solid

color 

White to off-white

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1-(4-AMino-phenyl)-3-(4-tert-butyl-benzoyl)-thiourea Chemical Properties,Usage,Production

Biological Activity

tenovin sar studies aimed at increasing water solubility

Synthesis

Under argon protection, 4-tert-butylbenzoyl chloride (10 mmol, 1.97 g) was dissolved in acetone (20 mL), sodium thiocyanate (10 mmol, 0.81 g) was added, and the reaction was stirred for 2 hours. Subsequently, the above reaction mixture was slowly added dropwise to a solution of 1,4-phenylenediamine (20 mmol, 2.16 g) in acetone (50 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 36 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue obtained was dissolved in dichloromethane, filtered to remove insoluble material and the filtrate was concentrated again. Purification was carried out by silica gel column chromatography, eluting using a solvent mixture of ethyl acetate-petroleum ether. The target fraction was collected, concentrated and ground with ether to afford analytically pure N-((4-aminophenyl)thiocarbamoyl)-4-(tert-butyl)benzamide in a yield of 2.45 g (75% yield). The product characterization data were as follows: melting point 189-191°C; 1H-NMR (CDCl3) δ 1.36 (s, 9H), 6.81 (m, 2H), 7.47 (m, 2H), 7.54 (m, 2H), 7.81 (m, 2H), 9.05 (s, 1H), 12.41 (s, 1H); MS (ES+) m/z 350 [M + Na]+; elemental analysis calculated value C18H21N3ONaS 350.1300, measured value 350.1303.

References

[1] Patent: WO2008/29096, 2008, A2. Location in patent: Page/Page column 22-23; 34-35
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 5, p. 1779 - 1793