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4-Fluorophenylacetonitrile, also known as 4-fluorophenylacetonitrile, is an organic compound that serves as a starting reagent in the synthesis of various chemical compounds, particularly 1-Alkyl-N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide derivatives. It is characterized by its clear light yellow liquid appearance and plays a crucial role in the pharmaceutical and chemical industries due to its versatile reactivity and potential applications.

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  • 459-22-3 Structure
  • Basic information

    1. Product Name: 4-Fluorophenylacetonitrile
    2. Synonyms: P-FLUOROBENZYL CYANIDE;P-FLUOROPHENYLACETONITRILE;PARA-FLUOROBENZYL CYANIDE;(p-fluorophenyl)-acetonitril;4-fluoro-benzeneacetonitril;4-Fluorobenzeneacetonitrile;4-Fluorophenylaceticacidnitrile;Acetonitrile, (p-fluorophenyl)-
    3. CAS NO:459-22-3
    4. Molecular Formula: C8H6FN
    5. Molecular Weight: 135.14
    6. EINECS: 207-286-8
    7. Product Categories: Aromatic Nitriles;Nitrile;Fluorobenzene
    8. Mol File: 459-22-3.mol
  • Chemical Properties

    1. Melting Point: 86°C
    2. Boiling Point: 119-120 °C18 mm Hg(lit.)
    3. Flash Point: 227 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 1.126 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0535mmHg at 25°C
    7. Refractive Index: n20/D 1.5002(lit.)
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. BRN: 1907764
    11. CAS DataBase Reference: 4-Fluorophenylacetonitrile(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-Fluorophenylacetonitrile(459-22-3)
    13. EPA Substance Registry System: 4-Fluorophenylacetonitrile(459-22-3)
  • Safety Data

    1. Hazard Codes: Xn,T,Xi
    2. Statements: 20/21/22-36/37/38-20/21/22/36/37/38-20/20/22
    3. Safety Statements: 26-36-24/25-26/36/37/39
    4. RIDADR: UN 3276 6.1/PG 3
    5. WGK Germany: 3
    6. RTECS: AM0210000
    7. TSCA: T
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 459-22-3(Hazardous Substances Data)

459-22-3 Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorophenylacetonitrile is used as a starting reagent for the synthesis of 1-Alkyl-N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide derivatives, which are important in the development of new pharmaceutical compounds. These derivatives have potential applications in the treatment of various medical conditions, making 4-Fluorophenylacetonitrile a valuable component in the drug discovery process.
Used in Chemical Synthesis:
In the chemical industry, 4-Fluorophenylacetonitrile is used as an intermediate in the synthesis of various organic compounds. Its unique chemical properties, such as its clear light yellow liquid appearance, make it a versatile building block for creating a wide range of products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
4-Fluorophenylacetonitrile is also utilized in research and development laboratories for the exploration of new chemical reactions and the development of innovative synthetic methods. Its reactivity and structural features make it an attractive candidate for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and catalyst design.

Biochem/physiol Actions

4-Fluorophenylacetonitrile undergoes biotransformation to 4-Fluorophenylacetic acid by marine fungi, Aspergillus sydowii Ce19.

Check Digit Verification of cas no

The CAS Registry Mumber 459-22-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 9 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 459-22:
(5*4)+(4*5)+(3*9)+(2*2)+(1*2)=73
73 % 10 = 3
So 459-22-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H6FN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

459-22-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A14290)  4-Fluorophenylacetonitrile, 98+%   

  • 459-22-3

  • 5g

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A14290)  4-Fluorophenylacetonitrile, 98+%   

  • 459-22-3

  • 25g

  • 519.0CNY

  • Detail
  • Alfa Aesar

  • (A14290)  4-Fluorophenylacetonitrile, 98+%   

  • 459-22-3

  • 100g

  • 1964.0CNY

  • Detail

459-22-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Fluorophenylacetonitrile

1.2 Other means of identification

Product number -
Other names Benzeneacetonitrile, 4-fluoro-

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:459-22-3 SDS

459-22-3Relevant articles and documents

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.

supporting information, p. 87 - 93 (2021/11/03)

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

Kim, Kunsoon,Lee, Seulchan,Hong, Soon Hyeok

supporting information, p. 5501 - 5505 (2021/07/26)

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei

supporting information, p. 7082 - 7086 (2021/02/26)

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Juhl, Martin,Petersen, Allan R.,Lee, Ji-Woong

, p. 228 - 232 (2020/11/30)

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Dong, Yanan,Li, Yuehui,Yang, Peiju,Zhao, Shizhen

, (2020/08/19)

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng

, p. 7621 - 7627 (2017/07/26)

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond

Wang, Sheng,Zhang, Xiaowei,Cao, Chengyao,Chen, Chao,Xi, Chanjuan

supporting information, p. 4515 - 4519 (2017/10/13)

A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.

supporting information, p. 50 - 53 (2015/07/28)

The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)

Ametoctradin is a Potent Qo Site Inhibitor of the Mitochondrial Respiration Complex III

Zhu, Xiaolei,Zhang, Mengmeng,Liu, Jingjing,Ge, Jingming,Yang, Guangfu

, p. 3377 - 3386 (2015/04/14)

Ametoctradin is a new Oomycete-specific fungicide under development by BASF. It is a potent inhibitor of the bc1 complex in mitochondrial respiration. However, its detailed action mechanism remains unknown. In the present work, the binding mode of ametoctradin was first uncovered by integrating molecular docking, MD simulations, and MM/PBSA calculations, which showed that ametoctradin should be a Qo site inhibitor of bc1 complex. Subsequently, a series of new 1,2,4-triazolo[1,5-a]pyrimidine derivatives were designed and synthesized to further understand the substituent effects on the 5- and 6-position of 1,2,4-triazolo[1,5-a]pyrimidine. The calculated binding free energies (ΔGcal) of newly synthesized analogues as Qo site inhibitors correlated very well (R2 = 0.96) with their experimental binding free energies (ΔGexp). Two compounds (4a and 4c) with higher inhibitory activity against porcine SQR than ametoctradin were successfully identified. The structural and mechanistic insights obtained from the present study will provide a valuable clue for future designing of a new promising bc1 inhibitor.

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

Lindsay-Scott, Peter J.,Clarke, Aimee,Richardson, Jeffery

, p. 476 - 479 (2015/03/05)

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

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