919950
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:
Molecular Weight:
294.37
MDL number:
UNSPSC Code:
12352106
NACRES:
NA.22
Pricing and availability is not currently available.
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Quality Level
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
Supporting products
PdCl2(dppf): 697230
Ag2O: 226831
related product
Product No.
Description
Pricing
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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William D Lambert et al.
Journal of the American Chemical Society, 141(43), 17068-17074 (2019-10-12)
Described is a general method for the installation of a minimal 6-methyltetrazin-3-yl group via the first example of a Ag-mediated Liebeskind-Srogl cross-coupling. The attachment of bioorthogonal tetrazines on complex molecules typically relies on linkers that can negatively impact the physiochemical
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