10036-43-8

Basic information

• Product Name: 3-FLUOROBENZYL CYANIDE
• Synonyms: 3-FLUOROBENZYL CYANIDE 97%;Jrd-0527;alpha-Fluorobenzeneacetonitrile;2-fluoro-2-phenylacetonitrile
• CAS NO: 10036-43-8
• Molecular Formula: C₈H₆FN
• Molecular Weight: 135.14
• EINECS: 207-918-2
• Mol File: 10036-43-8.mol

Chemical Properties

• Boiling Point: 226.8 °C at 760 mmHg
• Flash Point: 83.1 °C
• Appearance: /
• Density: 1.127 g/cm³
• Vapor Pressure: 0.0802mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: 3-FLUOROBENZYL CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FLUOROBENZYL CYANIDE(10036-43-8)
• EPA Substance Registry System: 3-FLUOROBENZYL CYANIDE(10036-43-8)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R36/37/38:
• Safety Statements: S26:; S37/39:
• Hazardous Substances Data: 10036-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorobenzyl cyanide is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Fluorobenzyl cyanide is utilized as an intermediate in the production of agrochemicals, aiding in the creation of compounds that can enhance crop protection and yield.
Used in Aromatic Compounds and Dyes Production:
3-Fluorobenzyl cyanide is used as a precursor in the manufacturing process of aromatic compounds and dyes, providing a foundation for the creation of a wide range of colorants and fragrances used in various industries.

InChI:InChI=1/C8H6FN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2

Upstream product

• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 140-29-4 phenylacetonitrile 
• 532-28-5 (RS)-mandelonitrile 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 22692-94-0 α-fluorophenylacetic acid chloride 
• 17841-30-4 methyl (±)-2-fluoro-2-phenylacetate 
• 37167-62-7 bromo-phenyl-acetic acid methyl ester 
• 100-52-7 benzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 103-64-0 bromostyrene 
• 14204-07-0 2-fluoro-2-phenylacetamide 

Downstream Products

• 64068-24-2 phenyl-2 fluoro-2 amino-1 ethane chlorhydrate 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 

Relevant articles and documents

Selective electrofluorination of phenylacetonitrile and α-(phenylthio)acetonitrile - The role of sulfur and other operating parameters

Cyclic voltammetric and constant current electrolysis were employed to study the electrochemical fluorination of PhCH2CN and PhSCH2CN in Et3N · 3HF/CH3CN using Pt electrodes. The presence of a sulfur atom near the methylene group in PhSCH2CN ensures the oxidative fluorination of this compound at much lower potential (around 1.75 V) when compared to PhCH2CN (2.0 V in solvent-free Et3N · 3HF). Operating parameters such as drying the solvent, pre-electrolysis, polarity reversal, temperature, current density, and concentration of HF as well as Et3N in CH3CN medium show significant influence on the overall yield of more easily oxidisable PhSCH2CN when compared to PhCH2CN. Maximum yields of 23% in the case of PhCHFCN and 61% in the case of PhSCHFCN were achieved.

Use of Task-Specific Ionic liquid for selective electrocatalytic fluorination

[Chemical equation presented] Highly selective indirect anodic fluorination of organic compounds was successfully carried out for the first time by using a task-specific ionic liquid of iodoarene as a mediator in ionic liquid hydrogen fluoride salts.

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

Fluorinated cannabinoid CB2 receptor ligands: Synthesis and in vitro binding characteristics of 2-oxoquinoline derivatives

Cannabinoid receptor 2 (CB2) plays an important role in human physiology and the pathophysiology of different diseases, including neuroinflammation, neurodegeneration, and cancer. Several classes of CB2 receptor ligands, including 2-oxoquinoline derivatives, have been previously reported. We report the synthesis and results of in vitro receptor binding of a focused library of new fluorinated 2-oxoquinoline CB2 ligands. Twelve compounds, 13-16 18, 19, 21-24, 27, and 28 were synthesized in good yields in multiple steps. Human U87 glioma cells expressing either hCB1 (control) or hCB2 were generated via lentiviral transduction. In vitro competitive binding assay was performed using [3H]CP-55,940 in U87hCB1 and U87hCB2 cells. Inhibition constant (Ki) values of compounds 13-16, 18, 19, 21-24, 27, and 28 for CB2 were >10,000, 2.8, 5.0, 2.4, 22, 0.8, 1.4, >10,000, 486, 58, 620, and 2400 nM, respectively, and those for CB1 were >10,000 nM. Preliminary in vitro results suggest that six of these compounds may be useful for therapy of neuropathic pain, neuroinflammatory diseases and immune disorders. In addition, compound 19, with its subnanomolar Ki value, could be radiolabeled with 18F and explored for PET imaging of CB2 expression.

Synthesis of β-fluorophenethyl halopyridyl thiourea compounds as non-nucleoside inhibitors of HIV-1 reverse transcriptase

Synthesis of β-fluorophenethylamines was accomplished in three steps with an overall yield of 50%. Condensation of β-fluorophenethylamine hydrochloride with thiocarbonylimidazole derivative derived from halopyridyl amines in dimethylformamide furnished the desired thiourea compounds as crystalline solids. Several of the β-fluorophenethyl thiourea compounds inhibited HIV-1 reverse transcriptase (RT) at nanomolar to low micromolar concentrations.

1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: A new selective fluorinating agent

The title compound has been prepared in 96-98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction of secondary and tertiary alcohols rapidly takes place at 0-10°C, producing corresponding alkyl fluorides as major product along with some olefins.

Effect of solvents on the selective electrofluorination of aromatic compounds containing active methylene groups

Voltammetry and constant current electrolysis was used to study the oxidative fluorination of PhSCH2COOMe, PhSCH2CONH2, PhSCH2COOPh and PhCH2CN in solvent-free and Et3N*3HF and Et3N*3HF dissolved in CH3CN, THF, DME and sulfolane. Sulfolane, DME and THF containig Et3N*3HF show much lower oxidation limits when compared to CH3CN/Et3N*3HF. These compounds udergo simultaneous oxidation along with background oxidation processes. Solvent-free Et3N*3HF has a much wider anodic potential range for the oxidation of organic compounds. Selective electrofluorination of PhSCH2COOPh does not show significant solvent effects. THF and DME were found to be more efficient for the selective fluorination of PhSCH2CONH2 and PhCH2CN compared to CH3CN. - Keywords: Selective electrofluorination; Active methylene compounds; Solvent effects

Selective electrolytic fluorinations in 70% HF/30% pyridine

The selective fluorination of compounds containing benzylic hydrogen atoms was accomplished by electrolysis in a mixture of 70% HF and 30% pyridine (Olah's reagent) using a square wave alternating current (1.76-2.75 V, 0.02-0.05 Hz) and Pt electrodes. This method can be used in the laboratory to prepare conveniently gram-size quantities of monofluorinated products. An ion radical mechanism has been proposed.

ELECTRFLUORATION EN POSITION BENZYLIQUE DANS LE SULFOLANE

The use of sulfolane as a solvent instead of acetonitrile in the electrofluorination of benzylic derivatives 1, (R=H, Cl) gives greater yields of benzylic fluorides 2, since the formation of acetamide byproducts 4 is prevented.However, the parallel fluorination of the aromatic nucleus is not avoided under these conditions.

MONO ET DIFLUORATION ELECTROCHIMIQUES DE GROUPES BENZYLIQUES

Anodic oxidation of benzylic compounds 1 using CH3CN as a solvent and Et3N,3HF as a fluorinating reagent allowed to introduce a fluorine atom in α position of electron withdrawing group via carbocation 1+ (ECBECN mechanism).Whatever the E group, monofluorides 2 are obtained in good yields from paramethoxy derivatives 1 (R=p-OCH3).In this case, by raising the potential of working electrode after the monofluorination step, gem difluorides 3 can be directly prepared from 1.When the substituent of the phenyl ring is different of a methoxy group, a mixture of fluoride 2 and acetamide 4 is generally obtained and the ratio of these two compounds is related to cation stability.