326-62-5

Basic information

• Product Name: 2-Fluorobenzyl cyanide
• Synonyms: O-FLUOROPHENYLACETONITRILE;2-fluoro-benzeneacetonitril;Acetonitrile, (o-fluorophenyl)-;o-Fluorobenzyl cyanide;2-FLUOROBENZYL CYANIDE;2-FLUOROPHENYLACETONITRILE;2-Fluorophdnylacetonitrile;2-Fluorophenylacetonitrile 2-Fluorobenzyl Cyanide o-Fluorobenzyl Cyanide
• CAS NO: 326-62-5
• Molecular Formula: C₈H₆FN
• Molecular Weight: 135.14
• EINECS: 206-313-0
• Product Categories: Fluorobenzene;Nitrile
• Mol File: 326-62-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 114-117 °C20 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: clear colorless to yellow-brownish liquid
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0822mmHg at 25°C
• Refractive Index: n20/D 1.5009(lit.)
• Storage Temp.: Flammables area
• BRN: 1862361
• CAS DataBase Reference: 2-Fluorobenzyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluorobenzyl cyanide(326-62-5)
• EPA Substance Registry System: 2-Fluorobenzyl cyanide(326-62-5)

Safety Data

• Hazard Codes: Xn,T,Xi,F
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 326-62-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorobenzyl cyanide is used as a synthetic intermediate for the production of (Z)-2-(2-fluorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile, which has potential applications in the development of pharmaceutical compounds.
Used in Chemical Synthesis:
2-Fluorobenzyl cyanide is used as a building block in the synthesis of various organic compounds, particularly those with fluorinated aromatic rings. Its unique chemical properties make it a valuable component in the creation of new molecules with specific characteristics and applications.

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

Upstream product

• 446-48-0 o-fluorobenzyl bromide 
• 143-33-9 sodium cyanide 
• 345-35-7 2-fluorobenzyl chloride 
• 140-29-4 phenylacetonitrile 
• 462-06-6 fluorobenzene 
• 107-14-2 chloroacetonitrile 
• 61317-65-5 1-(2,2-difluorovinyl)-2-fluorobenzene 
• 773837-37-9 sodium cyanide 
• 446-50-4 1-fluoro-2-(iodomethyl)benzene 
• 478163-07-4 2-fluorobenzyl methanesulfonate 
• 1159505-61-9 C₈H₇F₄NO₂S 
• 95-52-3 2-Fluorotoluene 
• 446-52-6 2-Fluorobenzaldehyde 
• 75-05-8 acetonitrile 

Downstream Products

• 572-98-5 2-(2-fluoro-phenyl)-4-phenyl-acetoacetonitrile 
• 154419-42-8 2-(2-fluorophenyl)-2-(6-chloro-3-pyridazinyl)acetonitrile 
• 76574-68-0 6-(2-Fluoro-phenyl)-2-methyl-pyrido[2,3-d]pyrimidin-7-ylamine 
• 100-17-4 para-methoxynitrobenzene 
• 30490-54-1 2-chloroacridine-10-carbonitrile 
• 77985-59-2 2-chloroacridine-10-carbonitrile N-oxide 
• 77778-85-9 (2-fluorophenyl)(4-nitrophenyl)methanone 
• 69584-88-9 4-(2-fluorophenyl)-1-methylpiperidine-4-carbonitrile 
• 122376-70-9 (2-Fluoro-phenyl)-pyridin-2-yl-acetonitrile 
• 726198-18-1 4-cyano-4-(2-fluorophenyl)-1-N-(tert-butyloxycarbonyl)piperidine 
• 859164-45-7 4-(2-fluorophenyl)tetrahydropyran-4-carbonitrile 
• 877125-75-2 4-(2-fluorophenyl)-1-methylpiperidine-4-carbonitrile hydrochloride 
• 80141-99-7 4-(2-fluorophenyl)-1-(4-methylphenylsulfonyl)-4-piperidine-carbonitrile 
• 255846-96-9 1-{[4-cyano-5-methyl-4-(2-fluorophenyl)hexyl]}-4-[2-(4-fluorophenoxy)ethyl]piperazine 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

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

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.).

Synthetic method of prasugrel intermediate o-fluorophenylacetic acid

The invention discloses a synthetic method of prasugrel intermediate o-fluorophenylacetic acid. The reaction process comprises the steps that (1) 2-fluorotoluene, N-halosuccinimide, an initiator and asolvent S1 are mixed uniformly, protective gas is introduced, the pressure is controlled to be 1.5-2 atmospheric pressure, the temperature is controlled to be 90-120 DEG C, stirring reaction is conducted for 1-2 h, and a mixture M1 is obtained; (2) a catalyst is mixed uniformly with a cyanide aqueous solution, the pressure is controlled to be 2-3 atmospheric pressure, the temperature is controlled to be 80-100 DEG C, the mixture M1 is added into a reaction system, then conditions are maintained to continue the reaction for 1-2 h, still standing and layering are conducted, organic phase is collected and concentrated to 1/2 of the original volume, and a mixture M2 is obtained; and (3) the mixture M2 is mixed uniformly with hydrochloric acid and glacial acetic acid, refluxing is conducted for 40-55 min, the mixture is poured into crushed ice after cooling, a solvent S2 is added for extraction, and after the organic phase is dried by a drying agent, a product is obtained by concentratingby a rotary evaporator. According to the synthetic method, safety and reliability are achieved, the production cost is low, three wastes are basically avoided, and the synthetic method is suitable forindustrial production.

A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile

A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.

AN IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL HYDROCHLORIDE AND ITS INTERMEDIATES

The present invention provides an improved process for the preparation of prasugrel and its pharmaceutical acceptable salt. Prasugrel chemically known as 2-acetoxy-5-(a- cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine or 5-[2- cyclopropyl-l-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2,-c]pyridine- 2yl acetate and having the structural formula (I) and its pharmaceutically acceptable salts. The present invention also provides an improved process for the preparation of cyclopropyl 2-fluorobenzyl ketone, 2-Fluoro-a-cyclopropyl carbonylbenzyl bromide, 5,6,7,7a Tetrahydro-4H- theino-[3,2-c]- pyridone-2 p-toluenesulfonate and its hydrochloride salt.

PALLADIUM-CATALYZED ORTHO-FLUORINATION

A new method of ortho-fluorination where an aryl C—H bond is directly replaced by an aryl C-F bond in a palladium-catalyzed reaction is provided. The method includes the ortho-fluorination of a triflamide protected benzylamine, a palladium catalyst, such as Pd(OTf)2, a fluorinating reagent such as N-fluoro-2,4,6-trimethylpyridinium triflate, and a ligand to promote the reaction such as N-methylpyrrolidinone (NMP).

Efficient synthesis of prasugrel, a novel P2Y12 receptor inhibitor

An efficient synthesis of prasugrel, a novel P2Y12 receptor inhibitor, is described. The cyclopropyl-phenylethanone intermediate was prepared by cyanide substitution, bromination, N-substitution, and the Grignard reaction. After acid hydrolyzation of the methyl ether and subsequent acetylation, the title product was obtained with a total yield of 21% after 10 linear steps from simple and commercially available raw materials.

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).

Versatile Pd(OTf)2·2H2O-catalyzed ortho-fluorination using NMP as a promoter

(Chemical Equation Presented) Pd(OTf)2·2H 2O-catalyzed ortho-fluorination of triflamide-protected benzylamines is reported. The use of N-fluoro-2,4,6-trimethylpyridinium triflate as the F+ source and NMP as a promoter is crucial for this reaction. The conversion of triflamide into a wide range of synthetically useful functional groups makes this fluorination protocol broadly applicable in medicinal chemistry and synthesis.

Synthesis of 7-cyano- and 7-acetamido-indoles via cyanocarbonation/hydrogenation of 7-formyl indole

A procedure for the synthesis of 7-cyano and 7-acetamido indoles via cyanocarbonation/hydrogenation of 7-formyl indole is presented. The process can be efficiently scaled up to provide multigram quantities of the desired compounds in good yield. A small survey of substrate scope indicates that the reaction may prove generally useful for the synthesis of aryl acetonitriles.