2-[(azidosulfonyl)oxy]-1,1,1-trichloroethane

EN300-46591695

Product class

Building Blocks

CAS number

1186018-19-8

MW

254.48

Purity

95%

Stock Availability

UA

Lead time

from 7 days delivery time

Reagent for photochemical amination of thioethers and sulfoxides

Tces3 (shortly for trichloroethoxysulfonyl azide) is a reagent for amination in the photochemical (UVA) continuous flow process of thioethers and sulfoxides[1], [2]. Sulfilimines and sulfoximines are highly valuable building blocks due to their importance in biologically active agents and this reagent offers a simple solution with high yields. The reaction proceeds at room temperature with a residence time below 2 hours using UVA light[1], [2]. A chiral reagent is also compatible with these reaction conditions to produce easily separable diastereomeric sulfilimines. The Tces protecting group could be easily cleaved from sulfoximine using zinc in acetic acid to afford free sulfoximine[1].

Synonyms: 2,2,2-Trichloroethoxysulfonyl azide

1. Iron-Catalyzed Amination of Sulfides and Sulfoxides with Azides in Photochemical Continuous Flow Synthesis. Lebel H.; Piras H.; Borduy M. ACS Catal 2016, 6 (2), 1109–1112. DOI: 10.1021/acscatal.5b02495 2. 2,2,2-Trichloroethoxysulfonyl Azide. Lebel H. Encyclopedia of Reagents for Organic Synthesis 2017, 1–2. DOI: 10.1002/047084289X.rn02034

Name:

2-[(azidosulfonyl)oxy]-1,1,1-trichloroethane

SMILES:

[N-]=[N+]=NS(=O)(=O)OCC(Cl)(Cl)Cl

CAS number:

1186018-19-8

Product class:

Building Blocks

ACD number:

MFCD35252516

Dangerous good:

Yes

Class:

Azides

Formula:

C₂H₂Cl₃N₃O₃S

Subclass:

Acylated Azides

MW:

254.48