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Merck
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重要文件

919950

Sigma-Aldrich

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

>98%

同義詞:

b-Tz, Minimal tetrazine

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About This Item

經驗公式(希爾表示法):
C16H14N4S
CAS號碼:
分子量::
294.37
MDL號碼:
分類程式碼代碼:
12352106
NACRES:
NA.22
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品質等級

化驗

>98%

形狀

powder

反應適用性

reaction type: click chemistry

SMILES 字串

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

InChI 密鑰

YATUIOCNNCZRCH-UHFFFAOYSA-N

應用

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

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°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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