64248-63-1

Basic information

• Product Name: 3,5-Difluorobenzonitrile
• Synonyms: 5-CYANO-1,3-DIFLUOROBENZENE;3,5-DIFLUOROBENZONITRILE;LABOTEST-BB LT00847812;3,5-Difluorobenzonitril;Benzonitrile, 3,5-difluoro- (9CI);3,5-Difluorobenzonitrile,99%;3,5-DIFLUOROBENZEONITRILE;3,5-Difluorobenzonitrile98%
• CAS NO: 64248-63-1
• Molecular Formula: C₇H₃F₂N
• Molecular Weight: 139.1
• EINECS: 264-752-3
• Product Categories: NITRILE;Fluorobenzene Series;FINE Chemical & INTERMEDIATES;Aromatic Nitriles;Fluorobenzene;Fluorobenzonitrile Series;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Fluorine series;Pyrazines
• Mol File: 64248-63-1.mol

Chemical Properties

• Melting Point: 84-86 °C(lit.)
• Boiling Point: 160 °C
• Flash Point: 56 °C
• Appearance: white crystals
• Density: 1.2490 (estimate)
• Vapor Pressure: 1.58mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• BRN: 2082206
• CAS DataBase Reference: 3,5-Difluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Difluorobenzonitrile(64248-63-1)
• EPA Substance Registry System: 3,5-Difluorobenzonitrile(64248-63-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39-36/37
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 64248-63-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Difluorobenzonitrile is used as an intermediate in the synthesis of pharmaceutical compounds for its unique reactivity and properties. Its fluorinated aromatic ring and nitrile group make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 3,5-Difluorobenzonitrile serves as a key intermediate for the preparation of various organic compounds. Its ability to participate in a range of chemical reactions, such as nucleophilic substitution, addition, and cyclization, makes it a versatile component in the synthesis of complex organic molecules.
Used in Material Science:
3,5-Difluorobenzonitrile is utilized in the development of advanced materials, such as polymers and coatings, due to its unique chemical and physical properties. Its incorporation into these materials can lead to improved performance characteristics, such as enhanced stability, durability, and specific functional properties tailored for various applications.

InChI:InChI=1/C7H3F2N/c8-6-1-5(4-10)2-7(9)3-6/h1-3H

Upstream product

• 125330-16-7 (3,5-difluorophenyl)diazirine 
• 930-69-8 sodium thiophenolate 
• 4110-35-4 3,5-dinitrobenzonitrile 
• 773-82-0 Pentafluorobenzonitrile 
• 461-96-1 3,5-difluorobromobenzene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 367-25-9 2,4-difluorophenylamine 
• 101471-20-9 2-bromo-4,6-difluoroaniline hydrobromide 
• 132980-99-5 3,5-difluorobenzamide 
• 156545-07-2 3,5-difluorophenylboronic acid 
• 119072-55-8 tert-butylisonitrile 
• 2265-91-0 1,3-difluoro-5-iodobenzene 
• 7321-55-3 2,2-dimethylmalononitrile 
• 79538-20-8 3,5-difluorobenzyl alcohol 

Downstream Products

• 90390-27-5 3,5-difluorobenzylamine 
• 132980-99-5 3,5-difluorobenzamide 
• 156215-40-6 2-(3,5-difluorophenyl)benzo[d]thiazole 
• 135306-45-5 1-(3,5-difluorophenyl)-propan-1-one 
• 220954-16-5 3-fluoro-5-morpholinobenzonitrile 
• 181073-82-5 4-cyano-2,6-difluorobenzoic acid 
• 350-19-6 ethyl 3,5-difluorobenzoate 
• 210992-28-2 3-amino-5-fluoro-benzonitrile 
• 467442-15-5 3,5-difluoro-4-formylbenzonitrile 
• 467442-16-6 3,5-difluoro-4-(2-nitro-ethyl)-benzonitrile 

Relevant articles and documents

Diazaphospholene-Catalyzed Hydrodefluorination of Polyfluoroarenes with Phenylsilane via Concerted Nucleophilic Aromatic Substitution

The metal-free catalytic C-F bond activation of polyfluoroarenes was achieved with diazaphospholene as the catalyst and phenylsilane as the terminal reductant. Density functional theory calculations suggested a concerted nucleophilic aromatic substitution mechanism.

Method for efficiently synthesizing fluorine-containing compound

The invention discloses a method for efficiently synthesizing a fluorine-containing compound, and relates to the field of fluorine-containing compound synthesis. The method is a method for generating a corresponding fluorine atom substituted fluorine-containing compound by reacting aromatic chloride or activated chloride serving as a raw material with potassium fluoride under the action of a novel catalyst. The method disclosed by the invention has the advantages of good product selectivity, high efficiency, mild reaction conditions, simplicity and convenience in operation, convenience in application and the like.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature

The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp2 cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to SN2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).

Solvent-Free Aerobic Oxidation of Alcohols to Nitriles Catalyzed by Copper Iodide in Combination with a Quaternary Ammonium Modified TEMPO

A catalytic system consisting of N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecyl ammonium bromide (TEMPO-Q), CuI and 2,2′-bipyridine was established. This catalytic system (CuI/bpy/TEMPO-Q) showed high activity and good to excellent selectivity in the oxidative conversion of various alcohols to the corresponding nitriles with molecular oxygen as terminal oxidant and aqueous ammonia as nitrogen source under solvent-free conditions. Besides, the catalytic system also offers the advantages of simplified workup procedure. This protocol thus represents a greener pathway for the synthesis of nitriles from alcohols. Graphical Abstract: TEMPO-Q, a compound with both a TEMPO and a quaternary ammonium moieties, in combination with copper iodide and 2,2′-bipyridine as a catalytic system performed well in the oxidation of alcohols to nitriles with molecular oxygen as terminal oxidant in aqueous ammonia under solvent-free conditions. The catalytic system not only offers the advantages of simplified workup procedure, but also has high activity and selectivity due to the phase transfer catalysis of TEMPO-Q[Figure not available: see fulltext.]

Synthesis of aryl nitriles by palladium-assisted cyanation of aryl iodides using tert-butyl isocyanide as cyano source

Abstract A palladium-catalyzed synthesis of aryl nitriles by the cyanation of aryl iodides with tert-butyl isocyanide as cyano source has been developed. This novel and efficient method avoids the use of toxic cyanides. The reaction is easy-to-handle and shows good functional group compatibility.

Transnitrilation from Dimethylmalononitrile to Aryl Grignard and Lithium Reagents: A Practical Method for Aryl Nitrile Synthesis

An electrophilic cyanation of aryl Grignard or lithium reagents, generated in situ from the corresponding aryl bromides or iodides, by a transnitrilation with dimethylmalononitrile (DMMN) was developed. DMMN is a commercially available, bench-stable solid. The transnitrilation with DMMN avoids the use of toxic reagents and transition metals and occurs under mild reaction conditions, even for extremely sterically hindered substrates. The transnitrilation of aryllithium species generated by directed ortho-lithiation enabled a net C-H cyanation. The intermediacy of a Thorpe-type imine adduct in the reaction was supported by isolation of the corresponding ketone from the quenched reaction. Computational studies supported the energetic favorability of retro-Thorpe fragmentation of the imine adduct. (Chemical Equation Presented).

Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles

Various aryl bromides were efficiently converted into the corresponding aromatic nitriles in good yields by the treatment with Mg turnings and subsequently DMF, followed by treatment with molecular iodine and aq NH 3. The same treatment of aryl bromides, which are weakly reactive to Mg turnings, with iPrMgCl·LiCl and subsequently DMF, followed by the treatment with molecular iodine and aq NH3 also afforded the corresponding aromatic nitriles in good yields. On the other hand, when N-formylpiperidine was used instead of DMF, p-substituted β-bromostyrenes were converted into the corresponding p-substituted cinnamonitriles, i.e., α,β-unsaturated nitriles, in good to moderate yields by the same procedure. The reactions were carried out by means of a simple experimental procedure and did not require any toxic metal cyanides or expensive rare metals. Therefore, the present reactions are practical and environmentally benign one-pot methods for the preparation of aromatic nitriles, cinnamonitriles, and aliphatic nitriles from aryl bromides, β-bromostyrenes, and alkyl bromides, respectively, through the formation of Grignard reagents and their DMF or N-formylpiperidine adducts.

The first example for cyanation of arylboronic acids with nontoxic and inexpensive K4[Fe(CN)6]

Nontoxic and inexpensive K4[Fe(CN)6] is first introduced as a cyanating agent to cyanation of arylboronic acids. The present method is simple, practical, and allowed a wide range of substrates including functionalized phenylboronic acids, 1-naphthylboronic acid as well as heterocyclic boronic acids to be smoothly converted into the corresponding products in moderate to high yields.

Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere

Figure presented A copper-catalyzed reaction of α-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from α-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O2 was found to be incorporated into the β-carbon fragment as a carboxylic acid.