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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
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

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.

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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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