21797-74-0

Basic information

• Product Name: 2,8-dimethylphenoxathiine 10,10-dioxide
• CAS NO: 21797-74-0
• Molecular Formula: C₁₄H₁₂O₃S
• Molecular Weight: 260.3083
• Mol File: 21797-74-0.mol

Chemical Properties

• Boiling Point: 451.6°C at 760 mmHg
• Flash Point: 226.9°C
• Density: 1.326g/cm³
• Vapor Pressure: 6.4E-08mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: 2,8-dimethylphenoxathiine 10,10-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,8-dimethylphenoxathiine 10,10-dioxide(21797-74-0)
• EPA Substance Registry System: 2,8-dimethylphenoxathiine 10,10-dioxide(21797-74-0)

Safety Data

• Hazardous Substances Data: 21797-74-0(Hazardous Substances Data)

Upstream product

• 21797-73-9 2,8-dimethyl-phenoxathiine 
• 106-44-5 p-cresol 
• 106-38-7 para-bromotoluene 
• 1579-40-4 1,1'-oxybis(4-methyl-benzene) 

Relevant articles and documents

Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines

There are more than 400-reported bisbenzylisoquinoline alkaloids, many with interesting biological activity, but the reported syntheses are long and low yielding. As a result, there have been no systematic attempts at exploitation of the potential therapeutic applications. The concept of a sulfur 'stitch', restricting the conformational freedom of intermediates in the synthesis, will potentially allow analogues of the natural products to be prepared using relatively efficient routes. The synthesis of intermediate sulfur heterocycles is reported, based on 2,8-dimethylphenoxathiin, leading via 2,8-bis(bromomethyl) phenoxathiin-10,10-dioxide to a synthesis of 3,4,8,9-tetrahydro-13-oxa-6-thia-2, 10-diazapentacene, a key potential intermediate on the route to a variety of macrocyclic bisbenzylisoquinolines.

2,8-dimethylphenoxathiin 10-oxide

An important precursor to biologically active compounds, 2,8-dimethylphenoxathiin 10-oxide (C14H12-O2S), is found to adopt a folded geometry. The dihedral angles between the aromatic rings are 11.8 (2) and 15.4(2)° for the two independent molecules, with the S atoms lying out of the ring planes.

Parallel β-sheet conformation in macrocycles

Amino acids (Val, Phe) are combined with two rigid spacers phenoxathiin-4,6-dicarboxylic acid (5) and 2,8-dimethyl-4,6-bis(aminomethyl)phenoxathiin-10,10-dioxide (6) to synthesize the cyclic structures 1 (5-Val/Val-6) and 2 (5-Phe/Phe-6). The diacid and d