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

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

Uses

Used in Chemical Research and Development:
2,3,4,5-Tetrafluoropyridine is used as a key intermediate in the synthesis of various complex organic molecules and pharmaceutical compounds. Its unique properties, such as the presence of fluorine atoms, make it a valuable building block for the development of new chemical entities.
Used in Fluorine Chemistry:
2,3,4,5-Tetrafluoropyridine is used as a fluorinating agent in the preparation of other fluorinated compounds. The presence of fluorine atoms in its structure allows for the transfer of these atoms to other molecules, facilitating the synthesis of fluorinated products with potential applications in various industries.
Used in Pharmaceutical Industry:
2,3,4,5-Tetrafluoropyridine is used as a starting material for the synthesis of fluorinated drugs and drug candidates. The incorporation of fluorine atoms into drug molecules can improve their pharmacokinetic properties, such as solubility, stability, and bioavailability, leading to more effective therapeutic agents.
Used in Material Science:
2,3,4,5-Tetrafluoropyridine is used in the development of new materials with unique properties, such as fluorinated polymers and coatings. The presence of fluorine atoms in these materials can enhance their chemical stability, thermal resistance, and non-stick properties, making them suitable for various applications, including aerospace, automotive, and electronics industries.

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).

FLUORINATIONS WITH COMPLEX METAL FLUORIDES. PART 6. FLUORINATION OF PYRIDINE AND RELATED COMPOUNDS WITH CAESIUM TETRAFLUOROCOBALTATE(III)

Pyridine has been fluorinated over caesium tetrafluorocobaltate(III) (CsCo(III)F4) at 300-400 deg C to give a mixture of undecafluoro-N-methyl-pyrrolidine, bis(trifluoromethyl)amine, pentafluoropyridine and several polyfluoropyridines; the product composition depend to some extent on the geometry of the reactor.The fluorinations of pentafluoropyridine, piperidine and undecafluoropiperidine were also investigated.

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.