406205-74-1

Basic information

• Product Name: BAY 59-3074
• Synonyms: BAY 59-3074;3-[2-Cyano-3-(trifluoromethyl)phenoxy]phenyl4,4,4-trifluoro-1-butanesulfonicacidester
• CAS NO: 406205-74-1
• Molecular Formula: C18H13F6NO4S
• Molecular Weight: 453.358
• Product Categories: Pharmaceutical intermediate
• Mol File: 406205-74-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 490.569°C at 760 mmHg
• Flash Point: 250.488°C
• Appearance: /
• Density: 1.496g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: Store at +4°C
• CAS DataBase Reference: BAY 59-3074(CAS DataBase Reference)
• NIST Chemistry Reference: BAY 59-3074(406205-74-1)
• EPA Substance Registry System: BAY 59-3074(406205-74-1)

Safety Data

• Hazardous Substances Data: 406205-74-1(Hazardous Substances Data)

Usage

Uses

Bay 59-3074, is a novel cannabinoid CB1/CB2 receptor partial agonist with antihyperalgesic and antiallodynic effects.

Biological Activity

Novel CB 1 /CB 2 receptor partial agonist (K i values are 48.3 and 45.5 nM at human CB 1 and CB 2 receptors respectively). Orally active CB 1 agonist in vivo . Displays anti-hyperalgesic and antiallodynic properties in rat models of chronic neuropathic and inflammatory pain.

InChI:InChI=1/C18H13F6NO4S/c19-17(20,21)8-3-9-30(26,27)29-13-5-1-4-12(10-13)28-16-7-2-6-15(14(16)11-25)18(22,23)24/h1-2,4-7,10H,3,8-9H2

Relevant articles and documents

A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation

The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp3)-CF3 reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl)Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the fluoride-rebound mechanism, was translated into a protocol for the synthesis of 18F-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography.