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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:
MFCD31692192
UNSPSC Code:
12352116
PubChem Substance ID:
329768216
NACRES:
NA.22

form

solid

Quality Level

100

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

Related Categories

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
GHS07

Signal Word

Warning

Hazard Statements

H302

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

790451-VAR:
790451-50MG:
790451-BULK:
790451-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD1145
MKCP8648
MKBR0293V

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Mark R Karver et al.
Bioconjugate chemistry, 22(11), 2263-2270 (2011-09-29)
1,2,4,5-Tetrazines have been established as effective dienes for inverse electron demand [4 + 2] Diels-Alder cycloaddition reactions with strained alkenes for over 50 years. Recently, this reaction pair combination has been applied to bioorthogonal labeling and cell detection applications; however
Neal K Devaraj et al.
Bioconjugate chemistry, 19(12), 2297-2299 (2008-12-05)
Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast
Melissa L Blackman et al.
Journal of the American Chemical Society, 130(41), 13518-13519 (2008-09-19)
Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water

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