| Identification | More | [Name]
2-[(Diphenylmethyl)thio]acetic acid | [CAS]
63547-22-8 | [Synonyms]
2-[(DIPHENYLMETHYL)THIO]ACETIC ACID
2-PHENYL METHYLTHIO ACETIC ACID
AKOS BC-1797
BENZHYDRYLSULFANYL ACETIC ACID
(BENZHYDRYLTHIO)ACETIC ACID
2-(Diphenylmethyl)sulfide acetic acid
AKOS BC-179
Acetic acid, [(diphenylmethyl)thio]- | [Molecular Formula]
C15H14O2S | [MDL Number]
MFCD07787609 | [Molecular Weight]
258.34 | [MOL File]
63547-22-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Powder | [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) |
| Hazard Information | Back Directory | [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 |
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