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(4-(1,2,4,5-Tetrazin-3-yl)phenyl)methanamine hydrochloride

95%

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Synonym(s):
Benzylamino tetrazine hydrochloride, H-Tz-Bz-NH3Cl hydrochloride
Empirical Formula (Hill Notation):
C9H9N5 · xHCl
CAS Number:
Molecular Weight:
187.20 (free base basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

95%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

206-225 °C (decomposition)

functional group

amine

storage temp.

−20°C

SMILES string

NCC1=CC=C(C2=NN=CN=N2)C=C1.[H]Cl

InChI

1S/C9H9N5.ClH/c10-5-7-1-3-8(4-2-7)9-13-11-6-12-14-9;/h1-4,6H,5,10H2;1H

InChI key

FAAUXGMWUKVOPI-UHFFFAOYSA-N

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This Item
900913M0505ALD00554
vibrant-m

900913

Tetrazine-PEG5-NHS ester

vibrant-m

M0505

Methylamine hydrochloride

vibrant-m

ALD00554

5-phenyl-1,2,3-triazine

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

-

reaction suitability

-

form

solid

form

powder or crystals

form

powder or crystals

form

flakes

mp

206-225 °C (decomposition)

mp

-

mp

231-233 °C (lit.)

mp

141-146 °C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

functional group

amine

functional group

NHS ester

functional group

-

functional group

-

General description

4-(1,2,4,5-Tetrazin-3-yl)phenyl)methanamine is a 1,2,4,5-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.

Application

Amine functionalized tetrazine for inverse electron demand Diels-Alder cycloaddition reactions. The tetrazine will react with strained alkenes such as transcyclooctene, norbornene and cyclopropene to yield a stable covalent linkage. Tetrazines have proven useful in bioorthogonal reactions for many biological imaging and bioconjugation applications.

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pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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

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