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900744

Sigma-Aldrich

TMS-N-ethynyl-N,4-dimethylbenzenesulfonamide

≥95%

Synonym(s):

N,4-Dimethyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide, TMS-N-methylynetoluenesulfonamide, TMS-MTYsA

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About This Item

Empirical Formula (Hill Notation):
C13H19NO2SSi
Molecular Weight:
281.45
UNSPSC Code:
12352200

Assay

≥95%

form

solid

mp

55 °C

functional group

sulfonamide

storage temp.

2-8°C

SMILES string

CC1=CC=C(S(=O)(N(C)C#C[Si](C)(C)C)=O)C=C1

Application

TMS-N-ethynyl-N,4-dimethylbenzenesulfonamide (TMS-MTYsA) is an air- and moisture-stable ynamide demonstrated to be an efficient and high-yielding coupling reagent for selective amide and peptide bond formation under mild reaction conditions without racemization. The product is supplied as the TMS-protected ynamide, which can be easily deprotected in situ without isolating the product.

Other Notes

Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation.
Saito N, et al.
Organic & Biomolecular Chemistry, 14(42), 10080-10089 (2016)
Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis.
Hu L, et al.
Journal of the American Chemical Society, 138(40), 13135-13138 (2016)
Gold-Catalyzed Intermolecular Nitrene Transfer from 2 H-Azirines to Ynamides: A Direct Approach to Polysubstituted Pyrroles.
Zhu L, et al.
Organic Letters, 17(1), 30-33 (2014)
Regio-and Stereoselective Synthesis of 2-Amino-1, 3-diene Derivatives by Ruthenium-Catalyzed Coupling of Ynamides and Ethylene.
Saito N, et al.
Organic Letters, 13(10), 2718-2721 (2011)

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