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790451

Sigma-Aldrich

TCO-amine HCl salt

Synonym(s):

trans-Cyclooctene-amine hydrochloride salt, TCO-NH2, HCl salt

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About This Item

Empirical Formula (Hill Notation):
C12H22N2O2 · HCl
Molecular Weight:
262.78
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

amine

storage temp.

−20°C

SMILES string

O=C(NCCCN)OC1CCC/C=C/CC1.[H]Cl

InChI

1S/C12H22N2O2.ClH/c13-9-6-10-14-12(15)16-11-7-4-2-1-3-5-8-11;/h1-2,11H,3-10,13H2,(H,14,15);1H/b2-1+;

InChI key

GIYQQURLGCGUKK-TYYBGVCCSA-N

Application

Amine functionalized trans-cyclooctene derivative for incorporation of the cyclooctene moiety into carboxyl containing compounds or biomolecules via standard coupling techniques (DCC; EDC etc...). Trans-cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1; 2; 4; 5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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