Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

900744

Sigma-Aldrich

TMS-N-ethynyl-N,4-dimethylbenzenesulfonamide

≥95%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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[1][2][3] under mild reaction conditions without racemization.[4] 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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

900744-250MG:
900744-5G:
900744-VAR:
900744-BULK:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service