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919950

Sigma-Aldrich

3-(([1,1′-Biphenyl]-4-ylmethyl)thio)-6-methyl-1,2,4,5-tetrazine

>98%

Synonym(s):

b-Tz, Minimal tetrazine

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About This Item

Empirical Formula (Hill Notation):
C16H14N4S
CAS Number:
2378619-75-9
Molecular Weight:
294.37
MDL number:
MFCD33021752
UNSPSC Code:
12352106
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

assay

>98%

form

powder

reaction suitability

reaction type: click chemistry

SMILES string

S(Cc2ccc(cc2)c3ccccc3)c1nnc(nn1)C

InChI key

YATUIOCNNCZRCH-UHFFFAOYSA-N

Related Categories

Application

3-(([1,1′-Biphenyl]-4-ylmethyl)thio)-6-methyl-1,2,4,5-tetrazine (b-Tz) is a minimal tetrazine derivative capable of undergoing [4+2] Diels-Alder cycloaddition reactions with strained alkenes, which makes it highly useful in bioorthogonal labeling and cell detection applications. Tetrazines are often incorporated into chemical probes or other small-molecule tools using linkers that may impact physicochemical properties or the performance of the resulting conjugate product. Here, Lambert et al demonstrated the linker-free incorporation of b-Tz via silver-mediated Liebeskind-Srogl cross-coupling with a variety of aryl and heteroaryl boronic acids. This ″minimal″ tetrazine approach will facilitate the introduction of tetrazine into diverse complex molecules and improved probes for live-cell imaging and in vivo chemistry.

Supporting products
PdCl2(dppf): 697230
Ag2O: 226831

Other Notes

Installation of Minimal Tetrazines through Silver-Mediated Liebeskind-Srogl Coupling with Arylboronic Acids

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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