129027-65-2

Basic information

• Product Name: 1H-1,2,3-Triazole-4-carboxaldehyde, 1-(1,1-dimethylethyl)- (9CI)
• Synonyms: 1H-1,2,3-Triazole-4-carboxaldehyde, 1-(1,1-dimethylethyl)- (9CI)
• CAS NO: 129027-65-2
• Molecular Formula: C₇H₁₁N₃O
• Molecular Weight: 153.18174
• Product Categories: ALDEHYDE
• Mol File: 129027-65-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1H-1,2,3-Triazole-4-carboxaldehyde, 1-(1,1-dimethylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-Triazole-4-carboxaldehyde, 1-(1,1-dimethylethyl)- (9CI)(129027-65-2)
• EPA Substance Registry System: 1H-1,2,3-Triazole-4-carboxaldehyde, 1-(1,1-dimethylethyl)- (9CI)(129027-65-2)

Safety Data

• Hazardous Substances Data: 129027-65-2(Hazardous Substances Data)

Usage

triazole derivative

contains a 1,2,3-triazole ring

carboxaldehyde functional group

a carbonyl group (C=O) bonded to a hydrogen atom and a carbon atom

tert-butyl group

a (C(CH3)3) group, providing stability and steric hindrance

used in organic synthesis and medicinal chemistry

as a building block for the synthesis of various bioactive molecules and pharmaceuticals

utilized in the development of new materials

for the creation of new compounds with unique properties

used in chemical research

for the study of its reactivity and potential applications.

Upstream product

• 129027-61-8 [1-(1-tert-Butyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-phenyl-amine 
• 133902-59-7 [1-(1-tert-Butyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-phenyl-amine 
• 133902-47-3 tert-Butyl-[1-(1-phenyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-amine 
• 129027-57-2 tert-Butyl-[1-(1-phenyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-amine 
• 1257633-67-2 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole 

Downstream Products

• 1334179-85-9 BTTAA 

Relevant articles and documents

CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITIONS (CUAAC) LIGANDS AND METHODS FOR CARRYING OUT CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITION REACTIONS

A Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core. A method for carrying out a Cu(I)-Catalyzed Azide-Alkyne Cycloaddition reaction, comprising: combining in a solution an alkyne-tagged component, an azide-tagged component and a Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core; filtering the solution through a solid phase extraction filter to remove Cu(I)-ligand catalyst and/or excess ligand.

Highly-efficient and versatile fluorous-tagged Cu(i)-catalyzed azide-alkyne cycloaddition ligand for preparing bioconjugates

A novel ligand (FBTTBE) for Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) has been developed, which demonstrates not only superior catalytic efficiency but also the ease of removing toxic copper species. FBTTBE has also been successfully applied in the synthesis of radiometal-labeled peptide and antibody without observable transchelation with the non-radioactive Cu(i) catalyst.

LIGANDS AND METHODS FOR LABELING BIOMOLECULES IN VIVO

Disclosed are tris(triazolylmethyl)amine ligands, and kits and methods for labeling and/or imaging a biomolecule of interest in a subject or living system.

Biocompatible copper(I) catalysts for in vivo imaging of glycans

The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is the standard method for bioorthogonal conjugation. However, current Cu(I) catalyst formulations are toxic, hindering their use in living systems. Here we report that BTTES, a tris(triazolylmethyl)amine-based ligand for Cu(I), promotes the cycloaddition reaction rapidly in living systems without apparent toxicity. This catalyst allows, for the first time, noninvasive imaging of fucosylated glycans during zebrafish early embryogenesis. We microinjected embryos with alkyne-bearing GDP-fucose at the one-cell stage and detected the metabolically incorporated unnatural sugars using the biocompatible click chemistry. Labeled glycans could be imaged in the enveloping layer of zebrafish embryos between blastula and early larval stages. This new method paves the way for rapid, noninvasive imaging of biomolecules in living organisms.

Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-α production in human whole blood

Tpl2 (cot/MAP3K8) is an upstream kinase of MEK in the ERK pathway. It plays an important role in Tumor Necrosis Factor-α (TNF-α) production and signaling. We have discovered that 8-halo-4-(3-chloro-4-fluoro-phenylamino)-6-[(1H-[1,2,3]triazol-4-ylmethyl)-a

Replacement of Aryl by Alkyl in 1-Substituted 1H-1,2,3-Triazole-4-carbaldehydes

1-Phenyl-1,2,3-triazole-4-carbaldehyde is readily transformed into 1-alkyl-1,2,3-triazole-4-carbaldehydes by thermal isomerization of the corresponding imines, followed by acid hydrolysis.

Molecular Rearrangements of 4-Iminomethyl-1,2,3-Triazoles. Replacement of 1-Aryl Substituents in 1H-1,2,3-Triazole-4-carbaldehydes

The two structural isomers, 4 and 5, of 1-substituted-4-iminomethyl-1,2,3-triazoles are interconvertible when heated in dimethyl sulfoxide at 80 deg C.The equilibrium position depends on the electronic properties of the R-substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p-chlorophenyl and p-nitrophenyl.An interesting application is the synthesis of 1-alkyl-1,2,3-triazole-4-carbaldehydes from 1-phenyl-1,2,3-triazole-4-carbaldehyde by Scheme I.The hydrazones 4i, j and the oxime 4k do not rearrange due to an unfavorable Z-configuration around the C=N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11.The structures of the products have been fully characterized by 13C nmr spectroscopy and the mechanistic details of the rearrangement are discussed.