1380500-93-5

Basic information

• Product Name: tert-butyl N-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]carbamate
• Synonyms: tert-butyl N-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]carbamate
• CAS NO: 1380500-93-5
• Molecular Weight: 287.321
• Mol File: 1380500-93-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: tert-butyl N-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl N-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]carbamate(1380500-93-5)
• EPA Substance Registry System: tert-butyl N-[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]carbamate(1380500-93-5)

Safety Data

• Hazardous Substances Data: 1380500-93-5(Hazardous Substances Data)

Upstream product

• 66389-80-8 tert-butyl N-[(4-cyanophenyl)methyl]carbamate 
• 3473-63-0 formamidine acetic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15996-76-6 4-cyanobenzylamine hydrochloride 
• 75-09-2 dichloromethane 
• 33233-67-9 4-(tert-Butoxycarbonylaminomethyl)benzoic acid 

Downstream Products

• 1345866-68-3 r (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride 
• 1092689-33-2 (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanamine hydrochloride 
• 1388851-19-1 (E)-4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 

Relevant articles and documents

REAGENTS AND METHODS FOR TETRAZINE SYNTHESIS

Disclosed herein are mono- and di-substituted tetrazines and methods of their preparation and converting an oxetanyl ester to a thio-substituted tetrazine, which is then converted to a mono-substituted tetrazine, a di-substituted tetrazine, or a vinylether disubstituted tetrazine.

Divergent Synthesis of Monosubstituted and Unsymmetrical 3,6-Disubstituted Tetrazines from Carboxylic Ester Precursors

Since tetrazines are important tools to the field of bioorthogonal chemistry, there is a need for new approaches to synthesize unsymmetrical and 3-monosubstituted tetrazines. Described here is a general, one-pot method for converting (3-methyloxetan-3-yl)methyl carboxylic esters into 3-thiomethyltetrazines. These versatile intermediates were applied to the synthesis of unsymmetrical tetrazines through Pd-catalyzed cross-coupling and in the first catalytic thioether reduction to access monosubstituted tetrazines. This method enables the development of new tetrazine compounds possessing a favorable combination of kinetics, small size, and hydrophilicity. It was applied to a broad range of aliphatic and aromatic ester precursors and to the synthesis of heterocycles including BODIPY fluorophores and biotin. In addition, a series of tetrazine probes for monoacylglycerol lipase (MAGL) were synthesized and the most reactive one was applied to the labeling of endogenous MAGL in live cells.

Metal-Free Synthetic Approach to 3-Monosubstituted Unsymmetrical 1,2,4,5-Tetrazines Useful for Bioorthogonal Reactions

A facile, efficient and metal-free synthetic approach to 3-monosubstituted unsymmetrical 1,2,4,5-tetrazines is presented. Dichloromethane (DCM) is for the first time recognized as a novel reagent in the synthetic chemistry of tetrazines. Using this novel approach 11 3-aryl/alkyl 1,2,4,5-tetrazines were prepared in excellent yields (up to 75 %). The mechanism of this new reaction, including the role of DCM in the tetrazine ring formation, has been investigated by 13C labeling of DCM, and is also presented and discussed as well as the photophysical and electrochemical properties.