2-[(Diphenylmethyl)thio]acetic acid Chemical Properties

Melting point:

127-1290C

Boiling point:

408.6±33.0 °C(Predicted)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

3.68±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C15H14O2S/c16-14(17)11-18-15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,16,17)

InChIKey

HTHFEDOFDBZPRX-UHFFFAOYSA-N

SMILES

C(O)(=O)CSC(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

63547-22-8(CAS DataBase Reference)

Safety Information

HS Code 

2930.90.2900

2-[(Diphenylmethyl)thio]acetic acid Usage And Synthesis

Chemical Properties

White Crystalline Powder

Uses

Intermediate in the preparation of Modafinil

Synthesis

General procedure for the synthesis of 2-[(diphenylmethyl)mercapto]acetic acid from diphenylmethanol and mercaptoacetic acid: mercaptoacetic acid (10.5 g, 7.92 mL, density = 1.325 g/mL, 0.114 mol) was added slowly and dropwise to a solution of trifluoroacetic acid (100 mL) in diphenylmethanol. During the dropwise addition, precipitate formation was observed within 30 minutes. The reaction mixture was stirred continuously for 3 hours at room temperature. Upon completion of the reaction, the precipitate was collected by filtration and washed sequentially with water (3 x 50 mL) and hexane. The crude product was purified by recrystallization from EtOAc/hexane mixed solvent to give colorless crystals of 2-[(diphenylmethyl)thio]acetic acid. Yield: 17.93 g (64% yield). Melting point: 121°C.

References

[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2984 - 2997
[2] Tetrahedron Asymmetry, 2004, vol. 15, # 6, p. 1053 - 1058
[3] Tetrahedron Asymmetry, 2005, vol. 16, # 21, p. 3507 - 3511
[4] Patent: US7553646, 2009, B2
[5] Molecules, 2012, vol. 17, # 9, p. 10446 - 10458

2-[(Diphenylmethyl)thio]acetic acid(63547-22-8)Related Product Information

• Mercaptoacetic acid
• Calcium thioglycolate
• POTASSIUM THIOGLYCOLATE
• Ammonium thioglycolate
• Sodium thioglycolate
• Methyl thioglycolate
• Thiosalicylic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 2-Ethylhexyl mercaptoacetate
• Phenylacetic acid
• Acetic anhydride
• (METHYLTHIO)ACETIC ACID
• Modafinil Carboxylate-d5 Methyl Ester
• 2-Benzhydrylsulphinylacetic acid
• ACETIC ACID, [(DIPHENYLMETHYL)SULFINYL]-, ETHYL ESTER
• Modafinil Carboxylate-d5
• Modafinil Carboxylate Methyl Ester
• (Diphenylmethyl)Thio Acetic Acid Ethyl Ester