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761591

Sigma-Aldrich

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

95%

Synonym(s):

Benzylamino tetrazine hydrochloride, H-Tz-Bz-NH3Cl hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C9H9N5 · xHCl
CAS Number:
1345866-68-3
Molecular Weight:
187.20 (free base basis)
MDL number:
MFCD23097050
UNSPSC Code:
12352116
PubChem Substance ID:
329766561
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

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
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000366284
0000366285
0000366284
0000366285
0000326014

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A Bone-Seeking trans-Cyclooctene for Pretargeting and Bioorthogonal Chemistry: A Proof of Concept Study Using 99mTc-and 177Lu-Labeled Tetrazines.
Yazdani A, et al.
Journal of Medicinal Chemistry, 59(20), 9381-9389 (2016)
Synthesis and evaluation of a series of 1, 2, 4, 5-tetrazines for bioorthogonal conjugation
Karver MR, et al.
Bioconjugate Chemistry, 22(11), 2263-2270 (2011)
Thermally Induced Silane Dehydrocoupling on Silicon Nanostructures.
Kim D, et al.
Angewandte Chemie (International Edition in English), 55(22), 6423-6427 (2016)
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
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
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