67815-54-7

Basic information

• Product Name: 3,4,5-Trifluoropyridine
• Synonyms: 3,4,5-Trifluoropyridine;3,3,3-Trifluoropropylmercaptan
• CAS NO: 67815-54-7
• Molecular Formula: C₅H₂F₃N
• Molecular Weight: 133.0712896
• Mol File: 67815-54-7.mol

Chemical Properties

• Melting Point: 188-190 °C
• Boiling Point: 89.4 °C at 760 mmHg
• Flash Point: 7.9 °C
• Appearance: /
• Density: 1.396 g/cm³
• Vapor Pressure: 66.2mmHg at 25°C
• Refractive Index: 1.424
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.75±0.28(Predicted)
• CAS DataBase Reference: 3,4,5-Trifluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trifluoropyridine(67815-54-7)
• EPA Substance Registry System: 3,4,5-Trifluoropyridine(67815-54-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 67815-54-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4,5-Trifluoropyridine is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs with improved efficacy and selectivity. Its presence in drug molecules can enhance their lipophilicity, metabolic stability, and binding affinity to target proteins, leading to better pharmacokinetic and pharmacodynamic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3,4,5-Trifluoropyridine is utilized as a building block for the synthesis of novel agrochemicals, including insecticides, herbicides, and fungicides. The introduction of fluorine atoms into these compounds can enhance their biological activity, selectivity, and environmental persistence, resulting in more effective and sustainable crop protection solutions.
Used in Organic Synthesis:
3,4,5-Trifluoropyridine is employed as a versatile reagent in organic synthesis, enabling the preparation of a diverse range of fluorinated heterocycles and other organic molecules. Its high reactivity allows for various functional group transformations and coupling reactions, expanding the scope of synthetic chemistry and facilitating the discovery of new molecular structures with potential applications in various fields.
Used as a Solvent in Chemical Reactions:
Due to its unique solvation properties, 3,4,5-Trifluoropyridine is used as a solvent in certain chemical reactions, particularly those involving fluorinated compounds or requiring specific solubility characteristics. Its ability to dissolve a wide range of substances and its compatibility with various reaction conditions make it a valuable tool in the optimization of synthetic processes.
However, it is important to note that 3,4,5-Trifluoropyridine's high reactivity and potential toxicity necessitate proper handling and storage to ensure safe use in laboratory and industrial settings.

InChI:InChI=1/C5H2F3N/c6-3-1-9-2-4(7)5(3)8/h1-2H

Upstream product

• 700-16-3 Pentafluoropyridine 
• 71902-33-5 3,5-difluoropyridine 
• 76469-41-5 2,3,5‐trifluoropyridine 
• 2875-18-5 2,3,5,6-tetrafluoropyridine 
• 851179-05-0 3,5,6-trifluoro-2-hydrazinopyridine 
• 851179-06-1 3,5-difluoro-2-hydrazinylpyridine 
• 851178-97-7 4-chloro-3,5-difluoro pyridine 

Downstream Products

• 1430745-37-1 (1R,3s,5S)-tert-butyl 3-((1r,4R)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 1430747-32-2 (1R,3s,5S)-tert-butyl 3-((1s,4S)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate 
• 1621525-20-9 3,5-difluoro-4-(3-iodo-1H-pyrazol-1-yl)pyridine 
• 1415818-18-6 5-(4-((1r,4r)-4-(3,5-difluoropyridin-4-yloxy)cyclohexyloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole 

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).

Removal of fluorine from and introduction of fluorine into polyhalopyridines: An exercise in nucleophilic hetarenic substitution

Starting from six industrially available fluorinated pyridines, an expedient access to all three tetrafluoropyridines (2-4), all six trifluoropyridines (5-10), and the five non-commercial difluoropyridines (11-14 and 16) was developed. The methods employed for the selective removal of fluorine from polyfluoropyridines were the reduction by metals or complex hydrides and the site-selective replacement by hydrazine followed by dehydrogenation-dediazotation or dehydrochlorination-dediazotation. To introduce an extra fluorine atom, a suitable precursor was metalated and chlorinated before being subjected to a chlorine/ fluorine displacement process.