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2,4-Difluorobenzonitrile, with the molecular formula C7H3F2N, is a white solid chemical compound that is insoluble in water but readily soluble in organic solvents. It is a versatile intermediate and building block in the synthesis of various agrochemicals, pharmaceuticals, and fine chemicals, playing a significant role in the chemical and pharmaceutical industries.

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  • 103496-86-2 Structure
  • Basic information

    1. Product Name: 2,4-DIFLUOROBENZONITRILE
    2. Synonyms: 2,4-Difluorobenzonitrileanion radical
    3. CAS NO:103496-86-2
    4. Molecular Formula: C7H3F2N
    5. Molecular Weight: 139.1
    6. EINECS: 223-523-8
    7. Product Categories: N/A
    8. Mol File: 103496-86-2.mol
  • Chemical Properties

    1. Melting Point: 45-50℃
    2. Boiling Point: 181.6°Cat760mmHg
    3. Flash Point: 63.6°C
    4. Appearance: /
    5. Density: 1.26g/cm3
    6. Vapor Pressure: 0.845mmHg at 25°C
    7. Refractive Index: 1.486
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 2,4-DIFLUOROBENZONITRILE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2,4-DIFLUOROBENZONITRILE(103496-86-2)
    12. EPA Substance Registry System: 2,4-DIFLUOROBENZONITRILE(103496-86-2)
  • Safety Data

    1. Hazard Codes:  Xn:Harmful;
    2. Statements: R20/21/22:; R36/37/38:;
    3. Safety Statements: S26:; S36/37/39:;
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 103496-86-2(Hazardous Substances Data)

103496-86-2 Usage

Uses

Used in Agrochemical Industry:
2,4-Difluorobenzonitrile is used as an intermediate in the production of various agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used in Pharmaceutical Industry:
2,4-DIFLUOROBENZONITRILE serves as a key intermediate in the synthesis of pharmaceuticals, aiding in the creation of novel drugs with improved therapeutic properties.
Used in Organic Synthesis:
2,4-Difluorobenzonitrile is utilized as a building block in organic synthesis for the manufacture of a wide range of fine chemicals, enhancing the diversity and complexity of chemical products.
It is crucial to handle 2,4-difluorobenzonitrile with care and implement proper safety measures during its use to ensure the well-being of individuals and the environment.

Check Digit Verification of cas no

The CAS Registry Mumber 103496-86-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,4,9 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 103496-86:
(8*1)+(7*0)+(6*3)+(5*4)+(4*9)+(3*6)+(2*8)+(1*6)=122
122 % 10 = 2
So 103496-86-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H3F2N/c8-6-2-1-5(4-10)7(9)3-6/h1-3H

103496-86-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4-DIFLUOROBENZONITRILE

1.2 Other means of identification

Product number -
Other names 2,4-Difluorobenzenecarbonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103496-86-2 SDS

103496-86-2Relevant articles and documents

Selective fluorodenitration of chloronitroaromatics

Beaumont, Andrew J.,Clark, James H.,Boechat, Nubia A.

, p. 25 - 30 (1993)

Nucleophilic fluorination of chloronitrobenzenes shows a strong bias for fluorodenitration rather than halogen exchange.

Fluorodenitrations using Tetramethylammonium Fluoride

Boechat, Nubia,Clark, James H.

, p. 921 - 922 (1993)

Tetramethylammonium fluoride activated by azeotropic drying in situ is an efficient reagent for the fluorodenitration of nitroaromatics.

Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides

Littke, Adam,Soumeillant, Maxime,Kaltenbach III, Robert F.,Cherney, Robert J.,Tarby, Christine M.,Kiau, Susanne

, p. 1711 - 1714 (2007)

New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides.

Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis

De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio

, (2021/11/10)

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

Catalytic Hydrodefluorination via Oxidative Addition, Ligand Metathesis, and Reductive Elimination at Bi(I)/Bi(III) Centers

Cornella, Josep,Katzenburg, Felix,Leutzsch, Markus,N?thling, Nils,Pang, Yue

supporting information, p. 12487 - 12493 (2021/08/30)

Herein, we report a hydrodefluorination reaction of polyfluoroarenes catalyzed by bismuthinidenes, Phebox-Bi(I) and OMe-Phebox-Bi(I). Mechanistic studies on the elementary steps support a Bi(I)/Bi(III) redox cycle that comprises C(sp2)-F oxidative addition, F/H ligand metathesis, and C(sp2)-H reductive elimination. Isolation and characterization of a cationic Phebox-Bi(III)(4-tetrafluoropyridyl) triflate manifests the feasible oxidative addition of Phebox-Bi(I) into the C(sp2)-F bond. Spectroscopic evidence was provided for the formation of a transient Phebox-Bi(III)(4-tetrafluoropyridyl) hydride during catalysis, which decomposes at low temperature to afford the corresponding C(sp2)-H bond while regenerating the propagating Phebox-Bi(I). This protocol represents a distinct catalytic example where a main-group center performs three elementary organometallic steps in a low-valent redox manifold.

Metal-free HNO3/TEMPO-catalyzed conversion of benzyl alcohols to aromatic nitriles with oxygen molecule as the terminal oxidant

Zhao, Bo,Ren, Yun-Lai,Ren, Fangping,Tian, Xinzhe,Zhao, Shuang

supporting information, p. 627 - 632 (2019/05/01)

A non-metal catalytic method for the aerobic conversion of primary alcohols to aromatic nitriles via a single-step operation was developed. A series of primary benzyl alcohols underwent this transformation to give the targeted products in moderate to high yields under the catalysis of TEMPO/ HNO3.

A process for preparing 2, 4 - difluoro phenyl nitrile (by machine translation)

-

, (2019/01/08)

The invention discloses a 2, 4 - difluoro phenyl nitrile preparation process, steps are as follows: (1) to 2, 4 - difluoro-benzoic acid and thionyl chloride as the raw material, produced by the reaction of 2, 4 - difluoro-benzoyl chloride; (2) the 2, 4 - difluoro-benzoyl chloride with ammonia water reaction, generating 2, 4 - difluoro-benzamide; (3) the 2, 4 - difluoro-benzamide with trifluoroacetic anhydride reaction, namely the preparation of the 2, 4 - difluoro phenyl nitrile. The invention relates to 2, 4 - difluoro phenyl nitrile synthetic reaction raw materials and synthetic route optimized design, the present invention adopted in the reaction raw material is cheap, it is safe to use; mild reaction conditions, does not need high temperature reaction, low requirements on the equipment, the yield of the product is high, high purity, easy to realize industrial production. (by machine translation)

A 4, 6 - double-halogenated isophthalonitrile preparation method (by machine translation)

-

, (2017/07/21)

The present invention relates to the technical field of the synthesis of pharmaceutical intermediates, in particular to a 4, 6 - double-halogenated isophthalonitrile preparation method, through the use of cheap and easily obtained 2, 4 - double-halo benzoic acid as the raw material, the reaction of the halide, the amidation reaction, dehydration reaction, the nitration reaction, reduction reaction, the diazotization reaction, the substitution reaction for the synthesis of 4, 6 - double-halogenated isophthalonitrile; the total yield can be 21.5%. The process route is easily obtained and cheap materials, few by-products, the purification treatment is the process is simple, easy to realize industrial production. (by machine translation)

Design and Synthesis of Novel 4-Phenoxyquinolines Bearing 3-Hydrosulfonylacrylamido or 1H-Imidazole-4-carboxamido Scaffolds as c-Met Kinase Inhibitors

Wang, Jiao,Xie, Lijun,Wang, Yu,Wang, Xiaoqiang,Xi, Shuancheng,Zeng, Tianfang,Gong, Ping,Zhai, Xin

, (2017/02/15)

A series of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing (E)-3-hydrosulfonylacrylamido or 1H-imidazole-4-carboxamido moieties were designed, synthesized and evaluated for their cytotoxicity against A549, MKN-45, and HT-29 cancer cell lines in vitro. All the target compounds showed moderate to significant cytotoxic activity against the tested cells with IC50 values ranging from 0.13 to 2.65 μM. Five of them were further examined for their inhibitory activity against c-Met kinase, which identified compound 30 as a promising agent (c-Met IC50 = 1.52 nM) with IC50 values of 0.24, 0.45, and 0.13 μM against HT-29, MKN-45, and A549 cells, respectively.

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

Kim, Kicheol,Hong, Soon Hyeok

supporting information, p. 2345 - 2351 (2017/07/22)

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.).

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