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
• Article Data: 2

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

General Description

3,4,5-Trifluoropyridine is a chemical compound with the molecular formula C5H2F3N. It is a colorless liquid with a strong odor, and it is primarily used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 3,4,5-Trifluoropyridine is a fluorinated derivative of pyridine, and its unique properties make it a valuable building block in the production of a variety of fluorinated compounds. It is also used as a solvent in chemical reactions and as a reagent in organic synthesis. Due to its high reactivity and potential for toxicity, proper handling and storage of 3,4,5-Trifluoropyridine is necessary 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

• 1621525-20-9 3,5-difluoro-4-(3-iodo-1H-pyrazol-1-yl)pyridine 
• 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 
• 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).