503596-47-2

Basic information

• Product Name: N-sulfinyltriphenylmethylamine
• CAS NO: 503596-47-2
• Molecular Weight: 305.4
• Mol File: 503596-47-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 98°C
• Boiling Point: 411.1±45.0 °C(Predicted)
• Density: 1.11±0.1 g/cm3(Predicted)
• CAS DataBase Reference: N-sulfinyltriphenylmethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-sulfinyltriphenylmethylamine(503596-47-2)
• EPA Substance Registry System: N-sulfinyltriphenylmethylamine(503596-47-2)

Safety Data

• Hazardous Substances Data: 503596-47-2(Hazardous Substances Data)

Usage

Description

N-sulfinyltriphenylmethylamine, also known as N-Sulfinyltritylamine (TrNSO), is a stable reagent used in the one-pot synthesis of various sulfonimidamides. It is characterized by its ability to join organometallic reagents and amines, making it a valuable compound in the field of chemical synthesis.

Uses

Used in Medicinal Chemistry:
N-sulfinyltriphenylmethylamine is used as a synthetic reagent for the assembly of differentially substituted sulfonimidamides. Its application is significant in medicinal chemistry due to its ability to produce high yields of these compounds, which are increasingly important in the development of new drugs.
Used in Agrochemistry:
N-sulfinyltriphenylmethylamine is also used as a synthetic reagent in agrochemistry. It aids in the efficient synthesis of sulfonimidamides, which are valuable for the development of new agrochemicals, contributing to more effective and sustainable agricultural practices.

Upstream product

• 5824-40-8 Triphenylmethylamin 

Relevant articles and documents

One-Pot, Three-Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N-Sulfinyltritylamine, TrNSO

Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry, but their preparation requires lengthy synthetic sequences, which has likely limited their use. We describe a one-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines. This convenient and efficient process uses a stable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale, as a linchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into a variety of differentially substituted sulfonimidamides containing medicinally relevant moieties, including pyridines and indoles. Analogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated.

Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides

Herein we report a practical and efficient copper-catalyzed approach for the conversion of various arenediazonium salts to the corresponding N-protected sulfonimidoyl fluorides. This operationally simple protocol tolerates a wide range of functional groups and can be applied to the late-stage modification of complex bioactive molecules. Furthermore, pharmaceutically important primary sulfonamides and sulfonimidamides derived from these valuable N-protected sulfonimidoyl fluoride units were prepared in minimal synthetic steps.

Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates

Sulfonimidamides are obtained in moderate to very good yields from the key intermediates O-benzotriazolyl sulfonimidates, which are formed by reacting aryldiazonium tetrafluoroborates, N-tritylsulfinylamine, and N-hydroxybenzotriazole hydrate in a process mediated by a tertiary amine. The formation of the sulfonimidate proceeds in inexpensive and environmentally benign dimethyl carbonate as the solvent, it does not require anhydrous conditions, and the product yields generally exceed 70 %. The substrate scope is broad, and a wide range of sensitive organic functionalities is well tolerated. The reactions probably proceed via aryl radicals formed from diazonium cations with assistance from both the tertiary amine and the sulfinylamine.