2265-94-3

Basic information

• Product Name: 3,5-Difluoronitrobenzene
• Synonyms: 3,5-Difluoronitrobenzene 99%;1,3-DIFLUORO-5-NITROBENZENE;3,5-DIFLUORONITROBENZENE;Benzene, 1,3-difluoro-5-nitro- (7CI,8CI,9CI);1-Nitro-3,5-difluorobenzene;3,5-Difluoro-1-nitrobenzene;5-Nitro-1,3-phenylene difluoride;3,5-Difluoronitrobenzene ,98%
• CAS NO: 2265-94-3
• Molecular Formula: C₆H₃F₂NO₂
• Molecular Weight: 159.09
• EINECS: 218-867-0
• Product Categories: HALIDE;Halides;Aromatic Halides (substituted);Miscellaneous;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2265-94-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 17 °C(lit.)
• Boiling Point: 176-177 °C(lit.)
• Flash Point: 165 °F
• Appearance: yellow or yellow-green liquid
• Density: 1.407 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.499(lit.)
• Storage Temp.: 2-8°C
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• CAS DataBase Reference: 3,5-Difluoronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Difluoronitrobenzene(2265-94-3)
• EPA Substance Registry System: 3,5-Difluoronitrobenzene(2265-94-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3265
• WGK Germany: 3
• RTECS: CZ5712000
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 2265-94-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

3,5-Difluoronitrobenzene has been used to improve thermal stability of immobilized porcine pancrease lipase.

General Description

Molecular structure of 3,5-difluoronitrobenzene was studied by gas-phase electron diffraction, MP2 ab initio and by B3LYP density functional calculations.

InChI:InChI=1/C6H3F2NO2/c7-4-1-5(8)3-6(2-4)9(10)11/h1-3H

Upstream product

• 99-35-4 1,3,5-trinitrobenzene 
• 98-95-3 nitrobenzene 
• 118-96-7 2,4,6-Trinitrotoluene 
• 880-78-4 pentafluoronitrobenzen 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 364-30-7 2-amino-3,5-difluoronitrobenzene 

Downstream Products

• 220954-15-4 N-4-(3-fluoro-5-nitrophenyl)morpholine 
• 803700-29-0 3-(3-fluoro-5-nitrophenoxy)pyridine 
• 803700-30-3 3-(3-fluoro-5-nitro-phenylsulfanyl)-pyridine 
• 528884-04-0 N-(3-amino-5-methylamino-phenyl)-N-methyl-acetamide 
• 528884-34-6 (3-amino-5-methylamino-phenyl)-methyl-carbamic acid tert-butyl ester 
• 790668-22-3 4-(3-fluoro-5-nitrophenylsulfonyl)-1-methylpiperidine 
• 790667-60-6 4-(3-fluoro-5-nitrophenoxy)-1-methylpiperidine 
• 857267-08-4 1-(3-fluoro-5-nitrophenyl)-4-methylpiperazine 
• 551956-00-4 3-fluoro-5-(1-methyl-3-trifluoromethyl-pyrazol-5-yloxy)-nitrobenzene 
• 7087-60-7 1-fluoro-3-methoxy-5-nitrobenzene 
• 1013655-23-6 1,1'-(5-nitro-1,3-phenylene)bis(1H-imidazole) 
• 1013655-25-8 C₁₀H₇N₇O₂ 
• 732245-92-0 1-[(R)-3-(3,5-difluoro-phenoxy)-piperidin-1-yl]-ethanone 
• 732245-91-9 1-[(R)-3-(3-fluoro-5-nitro-phenoxy)-piperidin-1-yl]-ethanone 

Relevant articles and documents

Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4

Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH4. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E/Z isomerization.

Synthesis of Aromatic Fluoro Compounds by Nucleophilic Exchange of Nitro Groups by Fluoride

The synthesis of aromatic fluoro compounds from the respective nitro compounds by nucleophilic substitution of nitrite by fluoride is described.Reasonable yields in case of nonactivated nitro compounds are only obtained if the nitrite formed in the reaction is eliminated by acylation. 1-Fluoro-3-nitrobenzene (2) was obtained from 1,3-dinitrobenzene (1), and 1-fluoro-3,5-dinitrobenzene (9) as well as 1,3-difluoro-5-nitrobenzene (10) from 1,3,5-trinitrobenzene (8) in yields up to 92percent by reaction of nitro compounds with potassium fluoride in sulfolane at 180-200 deg C in the presence of phthaloyl dichloride (6); 1,2-difluoro-4-nitrobenzene (12) was formed in 58percent yield from 2,4-dinitro-1-fluorobenzene (11) in the presence of pyromellitoyl tetrachloride (13).

SUBSTITUTION AND ADDITION REACTIONS OF NF4BF4 WITH AROMATIC COMPOUNDS

Benzene, toluene, and nitrobenzene interact rapidly with NF4BF4 in anhydrous HF to give, almost exclusively, fluorine substituted aromatic derivatives.Up to four hydrogens can be replaced in a rapid reaction, before a much slower addition reaction takes over.The direction of the substitution in C6H6, C6H5CH3 and C6H5NO2 and the lack of side chain fluorination in C6H5CH3 support an electrophilic substitution mechanism.These rapid substitution reactions are followed by much slower fluorine addition reactions to give the corresponding cyclo-hexadienes and -hexenes.These addition reactions were also studied separately using tetra-, penta-, and hexa- fluorobenzene as the starting materials.In these addition reactions, almost no hydrogen substitution occurred.The addition of the first pair of fluorines always gave 1,4-cyclohexadienes in which the CF2 group was adjacent to hydrogen on the ring.The addition of the second pair of fluorines resulted in the formation of cyclohexenes.These reactions occured in high yield and offer a controlled, high yield path to dienes.All products were characterized spectroscopically and by comparison to literature data.