17078-34-1

Basic information

• Product Name: 4-(hydroxymethyl)-2,3,5,6-tetrafluoroaniline
• Synonyms: 4-(hydroxymethyl)-2,3,5,6-tetrafluoroaniline
• CAS NO: 17078-34-1
• Molecular Weight: 195.116
• Mol File: 17078-34-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-(hydroxymethyl)-2,3,5,6-tetrafluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(hydroxymethyl)-2,3,5,6-tetrafluoroaniline(17078-34-1)
• EPA Substance Registry System: 4-(hydroxymethyl)-2,3,5,6-tetrafluoroaniline(17078-34-1)

Safety Data

• Hazardous Substances Data: 17078-34-1(Hazardous Substances Data)

Upstream product

• 126695-59-8 4-(hydroxymethyl)-2,3,5,6-tetrafluorophenyl azide 
• 120384-18-1 4-azido-2,3,5,6-tetrafluorobenzaldehyde 
• 653-37-2 perfluorobenzaldehyde 
• 944-43-4 4-amino-2,3,5,6-tetrafluorobenzoic acid 
• 440-60-8 (2,3,4,5,6-pentafluorophenyl)methanol 

Downstream Products

• 126695-59-8 4-(hydroxymethyl)-2,3,5,6-tetrafluorophenyl azide 
• 119060-58-1 4-amino-2,3,5,6-tetrafluorobenzyl aldehyde 

Relevant articles and documents

Tetrafluoroaryl azide as an N-Terminal capping group for click-To-dissolve diphenylalanine hydrogels

The synthesis of a bioorthogonal-responsive low molecular weight diphenylalanine (PhePhe)-based hydrogel that is capped with a 4-Azido-2,3,5,6-Tetrafluorobenzyl carbamate self-immolative linker is reported. The hydrogelator (AzF4-PhePhe) generates a stable hydrogel at 0.1 wt%, and rapidly reacts with the bioorthogonal reagent trans-cyclooctene (TCO), inducing a gel-To-solution transition. The critical gel concentration is five-fold lower than our previously synthesized non-fluorinated hydrogelator (Az-PhePhe), and the minimum concentration of TCO required for visible gel-To-solution transition in 24 hours is 1 mM. Doxorubicin can be encapsulated in the hydrogel and TCO-Triggered dissolution results in 76% and 89% release after 10 and 24 hours, respectively. Compared with our non-substituted aryl azide capping group used for Az-PhePhe, the tetrafluorinated aryl azide group improves the stability of the hydrogel in unbuffered water at a lower critical gel concentration, while improving sensitivity towards the bioorthogonal reagent TCO.

Switching on prodrugs using radiotherapy

Chemotherapy is a powerful tool in the armoury against cancer, but it is fraught with problems due to its global systemic toxicity. Here we report the proof of concept of a chemistry-based strategy, whereby gamma/X-ray irradiation mediates the activation of a cancer prodrug, thereby enabling simultaneous chemo-radiotherapy with radiotherapy locally activating a prodrug. In an initial demonstration, we show the activation of a fluorescent probe using this approach. Expanding on this, we show how sulfonyl azide- and phenyl azide-caged prodrugs of pazopanib and doxorubicin can be liberated using clinically relevant doses of ionizing radiation. This strategy is different to conventional chemo-radiotherapy radiation, where chemo-sensitization of the cancer takes place so that subsequent radiotherapy is more effective. This approach could enable site-directed chemotherapy, rather than systemic chemotherapy, with ‘real time’ drug decaging at the tumour site. As such, it opens up a new era in targeted and directed chemotherapy. [Figure not available: see fulltext.].

Mechanistic Evaluation of Bioorthogonal Decaging with trans-Cyclooctene: The Effect of Fluorine Substituents on Aryl Azide Reactivity and Decaging from the 1,2,3-Triazoline

Bioorthogonal prodrug activation/decaging strategies need to be selective, rapid and release the drug from the masking group upon activation. The rates of the 1,3-dipolar cycloaddition between a trans-cyclooctene (TCO) and a series of fluorine-substituted