1735-44-0

Basic information

• Product Name: 2,3,5,6-TETRAFLUORO-4-HYDRAZINOPYRIDINE
• Synonyms: 2,3,5,6-TETRAFLUORO-4-HYDRAZINOPYRIDINE;4-HYDRAZINO-2,3,5,6-TETRAFLUOROPYRIDINE
• CAS NO: 1735-44-0
• Molecular Formula: C₅H₃F₄N₃
• Molecular Weight: 181.09
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 1735-44-0.mol

Chemical Properties

• Melting Point: 56-57
• Boiling Point: 150.5 °C at 760 mmHg
• Flash Point: 44.8 °C
• Appearance: /
• Density: 1.706g/cm³
• Vapor Pressure: 3.84mmHg at 25°C
• Refractive Index: 1.53
• PKA: 3.10±0.40(Predicted)
• CAS DataBase Reference: 2,3,5,6-TETRAFLUORO-4-HYDRAZINOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAFLUORO-4-HYDRAZINOPYRIDINE(1735-44-0)
• EPA Substance Registry System: 2,3,5,6-TETRAFLUORO-4-HYDRAZINOPYRIDINE(1735-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1735-44-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3,5,6-Tetrafluoro-4-hydrazinopyridine is used as an intermediate in the synthesis of pharmaceuticals for its ability to inhibit ornithine decarboxylase, an enzyme involved in the production of polyamines, which are essential for cell growth and proliferation. This makes it a potential candidate in the development of drugs targeting conditions related to abnormal cell growth.
Used in Agricultural Chemical Synthesis:
In the agricultural industry, 2,3,5,6-tetrafluoro-4-hydrazinopyridine is used as a building block in the synthesis of various agricultural chemicals, contributing to the development of new compounds with potential applications in crop protection and enhancement of crop yield.
Used in Organic Compound Synthesis:
2,3,5,6-Tetrafluoro-4-hydrazinopyridine is utilized as a key component in the synthesis of a range of organic compounds, leveraging its unique structural features to create novel molecules with specific properties for various applications in research and industry.

InChI:InChI=1/C5H3F4N3/c6-1-3(12-10)2(7)5(9)11-4(1)8/h10H2,(H,11,12)

Upstream product

• 700-16-3 Pentafluoropyridine 
• 5350-57-2 benzophenone hydrazone 

Downstream Products

• 852333-80-3 N-(3-methyl-benzylidene)-N'-(2,3,5,6-tetrafluoro-pyridin-4-yl)-hydrazine 
• 39066-48-3 4,5-diphenyl-1-(tetrafluoro-4'-pyridyl)-1,2,3-triazol 
• 37756-65-3 (2,4-dinitro-phenyl)-(tetrafluoro-pyridin-4-yl)-amine 
• 39066-45-0 triphenyl-(4-imino-tetrafluoropyridyl)-phosphorane 
• 37756-87-9 (tetrafluoro-pyridin-4-yl)-(2,4,6-trinitro-phenyl)-amine 
• 3511-87-3 4-<4-(dimethylamino)phenylazo>-2,3,5,6-tetrafluoropyridine 
• 39066-50-7 5-phenyl-1-(tetrafluoro-4'-pyridyl)-1,2,3-Triazol 
• 39066-49-4 2,3,5,6-tetrafluoro-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine 
• 39077-43-5 2,3,5,6-tetrafluoro-N-phenylpyridin-4-amine 
• 1682-20-8 2,3,5,6-tetrafluoropyridin-4-amine 
• 39077-45-7 N-cyclohexyl-2,3,5,6-tetrafluoropyridin-4-amine 
• 39066-42-7 4-azido-2,3,5,6-tetrafluoropyridine 
• 16297-19-1 2,3,5,6-tetrafluoropyridin-4-yliodine 

Relevant articles and documents

PYRIDINE COMPOUNDS

This invention features compounds of formula (I): pharmaceutical compositions of the compounds, and methods of using the compounds for the treatment of, inter alia, IL-12-related diseases and disorders.

Reaction of pentafluoropyridine with lithium hydrazonides; competing monosubstitution at the 2- and 4-positions

Treatment of pentafluoropyridine (1) in diethyl ether with approximately 1 M equiv. of the hydrazonides Ph2C=NNHLi (3a) and Ph2C=NNLiPh (3b) under mild conditions gives good yields (62% and 83%) of 4- and 2-(Ph2C=NH)C5F4N (5a and 6a) and 4- and 2-(Ph2C=NPh)C5F4N (5b and 6b), respectively, containing unusually large amounts of 2-substituted products (5a/6a = 50:50; 5b/6b = 65:35). The increased ease of displacement of a 2-F substituent from 1 ( → 6a and 6b) in these cases is ascribed to chelation of the lithium cation in the transition state involved in the rate-determining step leading to formation of an ortho-quinonoidal σ-complex. Catalytic hydrogenation of a 1:1 mixture of hydrazones 5a and 6a affords the corresponding hydrazines, 4- and 2-H2NNHC5F4N (7 and 8) in good yield (78%); acidic hydrolysis (hot HC1 aq.) of the 5a/6a mixture yields tetrafluoro-4-hydrazinopyridine (9) and, depending on the conditions, tetrafluoro-2-hydrazinopyridine (10) or 2-aminotetrafluoropyridine (11).