68524-29-8

Basic information

• Product Name: Acetyl chloride, [(diphenylmethyl)thio]-
• CAS NO: 68524-29-8
• Molecular Formula: C15H13ClOS
• Molecular Weight: 276.787
• Mol File: 68524-29-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Acetyl chloride, [(diphenylmethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetyl chloride, [(diphenylmethyl)thio]-(68524-29-8)
• EPA Substance Registry System: Acetyl chloride, [(diphenylmethyl)thio]-(68524-29-8)

Safety Data

• Hazardous Substances Data: 68524-29-8(Hazardous Substances Data)

Upstream product

• 776-74-9 Bromodiphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 
• 63547-22-8 (benzhydrylthio)acetic acid 

Downstream Products

• 1502873-99-5 C₂₀H₁₉NO₅S 
• 1502874-00-1 C₁₉H₁₇NO₅S 
• 68524-30-1 2-(diphenylmethylthio)acetamide 
• 112111-43-0 Modafinil 
• 75384-14-4 3-Benzhydrylthio-1-diazo-2-propanon 
• 75384-18-8 Acetic acid 1-benzhydrylsulfanyl-2-oxo-propyl ester 
• 75384-17-7 1-acetoxy-3-benzhydrylthio-2-propanone 

Relevant articles and documents

Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification

A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.

Simple synthesis of modafinil derivatives and their anti-inflammatory activity

Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS and COX-2 after LPS stimulation. It was found that for sulfide analogues introduction of aliphatic groups on the amide part (compounds 11a-d) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11e-k). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12a-d) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12e-k) in BV-2 microglia cells.

Synthesis and determination of the absolute configuration of the enantiomers of modafinil

The asymmetric synthesis of both enantiomers of modafinil, a unique CNS stimulant with a reduced abuse liability, is described. This approach effectively prepares modafinil on a multigram scale in several steps from benzhydrol. The described synthetic route has also been used to produce the more water soluble analogue, adrafinil. X-ray crystallographic analysis on (-)-(diphenylmethanesulfinyl)acetic acid has determined the absolute configuration to be R.