1616955-03-3

Basic information

• Product Name: (Z)-tert-butyl (2-(5-chloro-2-formylstyryl)phenyl)carbamate
• Synonyms: (Z)-tert-butyl (2-(5-chloro-2-formylstyryl)phenyl)carbamate
• CAS NO: 1616955-03-3
• Molecular Weight: 357.837
• Mol File: 1616955-03-3.mol

Chemical Properties

• CAS DataBase Reference: (Z)-tert-butyl (2-(5-chloro-2-formylstyryl)phenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-tert-butyl (2-(5-chloro-2-formylstyryl)phenyl)carbamate(1616955-03-3)
• EPA Substance Registry System: (Z)-tert-butyl (2-(5-chloro-2-formylstyryl)phenyl)carbamate(1616955-03-3)

Safety Data

• Hazardous Substances Data: 1616955-03-3(Hazardous Substances Data)

Upstream product

• 1616954-93-8 tert-butyl (2-((5-chloro-2-(hydroxymethyl)phenyl)ethynyl)phenyl)carbamate 
• 13421-13-1 4-chloro-2-iodobenzoic acid 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 244104-55-0 (4-chloro-2-iodophenyl)methanol 
• 1616954-98-3 (Z)-tert-butyl (2-(5-chloro-2-(hydroxymethyl)styryl)phenyl)carbamate 

Relevant articles and documents

Synthesis of DIBAC analogues with excellent SPAAC rate constants

In search for increased reactivity in strain-promoted azide alkyne cycloadditions (SPAAC), the synthesis of new and more reactive cyclooctynes is of pivotal importance. To identify cyclooctynes with enhanced reactivity, without loss of stability, the synthesis and kinetic analysis of new dibenzoazacyclooctyne (DIBAC) analogues were conducted. Starting from iodobenzyl alcohol analogues and ortho-ethynylaniline various substituted dihydrodibenzo[b,f]azocines were produced. Subsequent bromination and elimination proved to be difficult depending on the aromatic substitution pattern, yielding chloro-, bromo-, and methoxy-substituted DIBACs in moderate yield. In the elimination reaction towards nitro- and Br,Cl-DIBAC, the corresponding cyclooctene was obtained instead of the cyclooctyne. Additionally, a dimethoxy-substituted DIBAC analogue was prepared following an alternative route involving light-induced deprotection of a cyclopropenone derivative. In total, four DIBAC analogues were successfully prepared showing excellent rate constants in the SPAAC reaction ranging from 0.45 to 0.9 M-1 s -1, which makes them comparable to the fastest cyclooctynes currently known. This journal is the Partner Organisations 2014.

SUBSTITUTED AZADIBENZOCYCLOOCTYNE COMPOUNDS AND THEIR USE IN METAL-FREE CLICK REACTIONS

The invention relates to a substituted azadibenzocyclooctyne compound according to Formula (5): The invention also relates to a conjugate wherein a substituted azadibenzocyclooctyne according to the invention is conjugated to a label, and to the use of these conjugates for bioorthogonal labeling, imaging or modification of a target molecule, e.g. surface modification. The invention further relates to a method for the modification of a target molecule, wherein a conjugate according to the invention is reacted with a compound comprising a 1,3-dipole or a 1,3-(hetero)diene.