2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone

CAS Number 86404-63-9

Chemistry Building Blocks, Fluorinated Building Blocks, Monomers

2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone MSDS

2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone CAS 86404-63-9

A fluorinated triazole building block

A synthesis intermediate for APIs in drug discovery and bioimaging

Overview
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2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone (CAS number 86404-63-9) has a difluoroacetophenone that is attached to a triazole unit. 2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone is a molecular scaffold for triazole antifungal medications, for instance, fluconazole, voriconazole and efinaconazole. The ketone moiety in 2,4-difluoro-(1H-1,2,4-triazolyl)acetophenone allows various modifications via Grignard reaction and aldol reaction. Enantioselective additions are also sufficient with chiral prolines catalysed aldol reaction or chiral auxiliaries assisted Grignard reaction.

Fluconazole chemical structure — Chemical structure of fluconazole, an antifungal drug

With the addition of chromophores, 2,4-difluoro-(1H-1,2,4-triazolyl)acetophenone has been used to study the mechanism of antifungal activity in live Candida cells, with fluorescent microscopy.

Multiple functional groups

For facile synthesis

Fluorinated triazole building block

For drug discovery, medicinal chemistry, and biochemistry research

Worldwide shipping

Quick and reliable shipping

High purity

>98% High purity

General Information

CAS Number	86404-63-9
Chemical Formula	C₁₀H₇F₂N₃O
Full Name	2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone
Molecular Weight	223.18 g/mol
Synonyms	1-(2,4-Difluorobenzoylmethyl)-1H-1,2,4-triazole, 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, Voriconazole Related Compound C, Fluconazole Impurity E
Classification / Family	Fluorinated building block, Heterocyclic building block, APIs, Bioimaging

Chemical Structure

Product Details

Purity	98%
Melting Point	T_m = 103 – 107 °C
Appearance	Off-white powder

MSDS Documentation

2,4-Difluoro-(1H-1,2,4-triazolyl)acetophenone MSDS Sheet

Literature and Reviews

Conazole, J. Heeres et al., Molecules, 15, 4129-4188(2010); DOI: 10.3390/molecules15064129.
Enantiomerically pure tertiary alcohols by TADDOL-assisted additions to ketones—or how to make a Grignard reagent enatioselective, B. Weber et al., Angew. Chem., Int. Ed., 31(1), 84–86(1992); DOI: 10.1002/anie.199200841.
Pharmacological significance of triazole scaffold, R. Kharb et al., J. Enzyme Inhib. Med. Chem., 26(1), 1-21(2011); DOI: 10.3109/14756360903524304.
Real-time imaging of the azole-class of antifungal drugs in live Candida cells, R. Benhamou et al., ACS Chem. Biol., 12(7), 1769–1777(2017); DOI: 10.1021/acschembio.7b00339.

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