S-TRITYL-3-MERCAPTOPROPIONIC ACID Chemical Properties

Melting point:

211-213°C

Boiling point:

503.8±38.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly, Heated), DMSO (Soluble), Methanol (Slightly)

pka

4.59±0.10(Predicted)

form 

Solid

color 

Off-White

Water Solubility 

Partly miscible in water.

Sensitive 

Air Sensitive

InChI

InChI=1S/C22H20O2S/c23-21(24)16-17-25-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2,(H,23,24)

InChIKey

AECGEIVNZGQBJT-UHFFFAOYSA-N

SMILES

C(O)(=O)CCSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

27144-18-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-23

S-TRITYL-3-MERCAPTOPROPIONIC ACID Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

Preparation and structural modification of 3-Tritylsulfanylpropionic Acid possesses antileukemic activity against leukemia.

Synthesis

General procedure for the synthesis of 3-(triphenylmethylthio)propionic acid from triphenylmethanol and 3-mercaptopropionic acid: 1. 100 g of 3-mercaptopropionic acid (942.15 mmol) was dissolved in 300 mL of glacial acetic acid at room temperature. 2. 245.27 g of triphenylmethanol (942.15 mmol) was dissolved in 736.79 mL of tetrahydrofuran (THF) at room temperature. 3. Slowly add the solution obtained from step 1 to the solution from step 2. 4. 16.62 g of concentrated sulfuric acid (98%, 169.587 mmol) is added slowly and dropwise at 28° C to 30° C. The reaction mixture is insulated. 5. The reaction mixture was stirred under insulating conditions for 4 hours. 6. Upon completion of the reaction, 360 g of solid crude product was obtained by filtration. 7. The crude product was dissolved in 720 mL of N,N-dimethylformamide (DMF). 8. 5 times the volume of water was added to the solution, filtered and dried to give 295.5 g of refined product in 90% yield. 9. The structure of the product was confirmed by infrared spectroscopy (IR) and nuclear magnetic resonance (NMR).

References

[1] Organic Letters, 2017, vol. 19, # 12, p. 3195 - 3198
[2] Patent: CN106380430, 2017, A. Location in patent: Paragraph 0017; 0018; 0019; 0020
[3] Chemical Communications, 2014, vol. 50, # 35, p. 4571 - 4574
[4] Australian Journal of Chemistry, 1990, vol. 43, # 3, p. 629 - 634
[5] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1448 - 1455

S-TRITYL-3-MERCAPTOPROPIONIC ACID(27144-18-9)Related Product Information

• N-Boc-S-Trityl-L-cysteine
• N-Fmoc-S-trityl-D-cysteine
• FMOC-CYS(MMT)-OH
• S-TRITYL-3-MERCAPTOPROPIONIC ACID
• FMOC-CYS(TRT)-OPFP
• FMOC-D-PEN(TRT)-OH
• FMOC-S-trityl-L-cysteine
• Fmoc-S-Trityl-L-penicillamine
• S-Trityl-L-cysteine
• 3-Mercaptopropionic acid
• TRT-CYS(TRT)-OH
• H-PEN(TRT)-OH
• TRT-CYS(TRT)-OH DEA
• BOC-PEN(TRT)-OH
• Fmoc-D-Cys(Trt)- OPfp
• BOC-D-PEN(TRT)-OH
• H-D-PEN(TRT)-OH
• AC-CYS(TRT)-OH