39769-09-0

Basic information

• Product Name: 4,4'-DIFLUOROBENZYLIDENEANILINE
• Synonyms: 4-FLUORO-N-(4-FLUOROBENZYLIDENE)ANILINE;4,4'-DIFLUOROBENZYLIDENEANILINE;N-(4-FLUOROBENZYLIDENE)-4-FLUOROANILINE;4,4''-DIFLUOROBENZYLIDENEANILIN;4,4''-DIFLUROBENZYLIDENEANILINE;N-(4-Fluorophenyl)-4-fluorobenzenemethanimine;p-Fluoro-N-(p-fluorobenzylidene)aniline;4,4'-Difluorobenzylideneaniline,98%
• CAS NO: 39769-09-0
• Molecular Formula: C₁₃H₉F₂N
• Molecular Weight: 217.21
• Mol File: 39769-09-0.mol

Chemical Properties

• Melting Point: 63-67 °C
• Boiling Point: 307.4±27.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• Solubility: soluble in Methanol
• PKA: 2.96±0.50(Predicted)
• CAS DataBase Reference: 4,4'-DIFLUOROBENZYLIDENEANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIFLUOROBENZYLIDENEANILINE(39769-09-0)
• EPA Substance Registry System: 4,4'-DIFLUOROBENZYLIDENEANILINE(39769-09-0)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-37/38-41-51/53
• Safety Statements: 26-36/39-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 39769-09-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 124573-82-6 (4-fluoro-phenyl)-(4-fluoro-phenylamino)-acetic acid 

Relevant articles and documents

Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes

The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.

Dialkyl diazomalonates in transition-metal-free, thermally promoted, diastereoselective wolff β-lactam synthesis

Metal-free, thermally promoted synthesis of 3-alkoxy-3-alkoxycarbonyl-2-azetidinones via the Wolff-Staudinger β-lactam synthesis using dialkyl diazomalonates is described. The reaction appears fairly general and delivers only one diastereomer.

Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts

CdSe/CdS core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious metal free transformation is easy to scale up and can be carried out by a one-pot protocol directly from aldehyde, amine, and thiophenol. Additional advantageous features of this protocol include a wide substrate scope, high yield of the amine products, extremely low catalyst loading (0.001 mol %), high turnover number (105), and the mild reaction conditions of using visible light or sun light at room temperature in neutral media.

Conversion of aldimines to secondary amines using iron-catalysed hydrosilylation

Iron-catalyzed hydrosilylation of imines to amines using a well-defined iron complex is reported. This method employs relatively mild conditions, by reaction of imine, (EtO)3SiH in a 1 : 2 ratio in the presence of 1 mol% precatalyst ([BIAN]Fe(η6-toluene), 3, BIAN = bis(2,6-diisopropylaniline)acenaphthene) at 70 °C. A broad scope of imines was readily converted into the corresponding secondary amines without the need for precatalyst activators.

Skeletal Diversity in Combinatorial Fashion: A New Format for the Castagnoli-Cushman Reaction

A new format for the Castagnoli-Cushman reaction of structurally diverse dicarboxylic acids, amines, and aldehydes in the presence of acetic anhydride as dehydrating agent is described. The reaction is distinctly amenable to parallel format: the combinato

TETRAHYDROISOQUINOLINONE DERIVATIVES AND THEIR USE IN THE INHIBITION OF THE HSP70 PROTEIN

The present invention relates to tetrahydroisoquinolinone derivatives of formula (I), pharmaceutical compositions comprising the same and the use of these derivatives in the inhibition of the Hsp70 protein. The compounds are useful in the treatment of cancer, autoimmune diseases, rheumatoid arthritis, inflammatory bowel disease and psoriasis. In formula (I) R1, R2 and R3 are optionally substituted phenyl, pyridinyl or pyrimidinyl; R4 is hydrogen or alkyl; R5 is halogen, hydroxy, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or -NR6 R7; R6 and R7 are hydrogen or alkyl; R8 is alkyl; and m is an integer of 0 to 3.

Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors

A series of novel human enterovirus 71 inhibitors, N-benzyl-N-phenylthiophene-2-carboxamide analogues, were synthesized and their antiviral activities were evaluated in vitro. Most derivatives of this structure against EV71 had a low micromolar range in the RD (rhabdomyosarcoma) cell lines. The most potent compound 5a, N-(4-bromobenzyl)-N-(4-fluorophenyl)thiophene-2-carboxamide, showed low micromolar activity against EV71 (EC50 = 1.42 μM) compared to the reference anti-EV71 drug enviroxime (EC50 = 0.15 μM). Preliminary SAR studies revealed that the thiophene-2-carboxamide core is crucial for maintaining antiviral activity, and N-substituent phenyl groups largely influenced the anti-EV71 efficacy of this new class of potent antiviral agents.

Synthesis, characterization and antimicrobial studies of some new quinoline incorporated benzimidazole derivatives

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Structural investigation of weak intermolecular interactions in fluorine substituted isomeric N-benzylideneanilines

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GREEN SYNTHESIS OF ARYL ALDIMINES USING ETHYL LACTATE

The present invention relates to a method for preparing aryl aldimines. In particular, the present invention relates to methods of preparing aryl aldimines that uses environmentally friendly solvent systems.