3512-16-1

Basic information

• Product Name: 2,3,4,5-Tetrafluoropyridine
• Synonyms: 2,3,4,5-Tetrafluoropyridine
• CAS NO: 3512-16-1
• Molecular Formula: C₅HF₄N
• Molecular Weight: 151.0617528
• Mol File: 3512-16-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 98.7°Cat760mmHg
• Flash Point: 13.5°C
• Appearance: /
• Density: 1.518g/cm³
• Vapor Pressure: 45.4mmHg at 25°C
• Refractive Index: 1.403
• CAS DataBase Reference: 2,3,4,5-Tetrafluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-Tetrafluoropyridine(3512-16-1)
• EPA Substance Registry System: 2,3,4,5-Tetrafluoropyridine(3512-16-1)

Safety Data

• Hazardous Substances Data: 3512-16-1(Hazardous Substances Data)

Usage

General Description

2,3,4,5-Tetrafluoropyridine is a type of organic compound which is often utilized in the field of chemistry, particularly in research and development. The key feature of this compound is the presence of fluorine atoms, granting it unique properties. It is included in the group of halopyridines, which are heterocyclic aromatic compounds where one or more hydrogen atoms in pyridine are replaced by a halogen atom. 2,3,4,5-Tetrafluoropyridine is represented by the molecular formula C5F4N, denoting the presence of carbon, fluorine, and nitrogen atoms. This chemical is also characterized by a molar mass of approximately 158.06 grams per mole.

InChI:InChI=1/C5HF4N/c6-2-1-10-5(9)4(8)3(2)7/h1H

Upstream product

• 700-16-3 Pentafluoropyridine 
• 56154-85-9 1-fluoromethyl-octafluoropyrrolidine 
• 110-86-1 pyridine 

Relevant articles and documents

Mechanistic study of Ru-NHC-catalyzed hydrodefluorination of fluoropyridines: The influence of the NHC on the regioselectivity of C-F activation and chemoselectivity of C-F versus C-H bond cleavage

We describe a combined experimental and computational study into the scope, regioselectivity, and mechanism of the catalytic hydrodefluorination (HDF) of fluoropyridines, C5F5-xHxN (x = 0-2), at two Ru(NHC)(PPh3)2(CO)H2 catalysts (NHC = IPr, 1, and IMes, 2). The regioselectivity and extent of HDF is significantly dependent on the nature of the NHC: with 1 HDF of C5F5N is favored at the ortho-position and gives 2,3,4,5-C5F4HN as the major product. This reacts on to 3,4,5-C5F3H2N and 2,3,5-C5F3H2N, and the latter can also undergo further HDF to 3,5-C5F2H3N and 2,5-C5F2H3N. para-HDF of C5F5N is also seen and gives 2,3,5,6-C5F4HN as a minor product, which is then inert to further reaction. In contrast, with 2, para-HDF of C5F5N is preferred, and moreover, the 2,3,5,6-C5F4HN regioisomer undergoes C-H bond activation to form the catalytically inactive 16e Ru-fluoropyridyl complex Ru(IMes)(PPh3)(CO)(4-C5F4N)H, 3. Density functional theory calculations rationalize the different regioselectivity of HDF of C5F5N at 1 and 2 in terms of a change in the pathway that is operating with these two catalysts. With 1, a stepwise mechanism is favored in which a N → Ru σ-interaction stabilizes the key C-F bond cleavage along the ortho-HDF pathway. With 2, a concerted pathway favoring para-HDF is more accessible. The calculations show the barriers increase for the subsequent HDF of the lower fluorinated substrates, and they also correctly identify the most reactive C-F bonds. A mechanism for the formation of 3 is also defined, but the competition between C-H bond activation and HDF of 2,3,5,6-C5F4HN at 2 (which favors C-H activation experimentally) is not reproduced. In general, the calculations appear to overestimate the HDF reactivity of 2,3,5,6-C5F4HN at both catalysts 1 and 2. (Chemical Equation Presented).

HIGHLY FLUORINATED HETEROCYCLES PART XV . THE METAL CATALYSED DEFLUORINATIVE REARRANGEMENT OF POLYFLUORINATED PYRROLIDINES TO POLYFLUOROPYRIDINES

Pyrolysis of a number of polyfluoro-1-alkyl pyrrolidines over iron gauze at 500-525o affords a small conversion to polyfluoropyridines.