80517-21-1

Basic information

• Product Name: 4-FLUORO-2-NITROBENZONITRILE
• Synonyms: 4-FLUORO-2-NITROBENZONITRILE;BUTTPARK 100\07-73;2-Cyano-5-fluoronitrobenzene
• CAS NO: 80517-21-1
• Molecular Formula: C₇H₃FN₂O₂
• Molecular Weight: 166.11
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Fluorine series
• Mol File: 80517-21-1.mol

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 311.6 °C at 760 mmHg
• Flash Point: 142.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.41 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-FLUORO-2-NITROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUORO-2-NITROBENZONITRILE(80517-21-1)
• EPA Substance Registry System: 4-FLUORO-2-NITROBENZONITRILE(80517-21-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• Hazardous Substances Data: 80517-21-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Upstream product

• 364-78-3 2-nitro-4-fluoroaniline 
• 151-50-8 potassium cyanide 
• 34662-32-3 4-chloro-2-nitrobenzonitrile 
• 448-39-5 N-(4-fluoro-2-nitrophenyl)acetamide 
• 13472-08-7 azobis(2-cyanobutane) 
• 394-01-4 4-fluoro-2-nitrobenzoic acid 
• 109-77-3 malononitrile 
• 364-77-2 4-fluoro-1-iodo-2-nitrobenzene 
• 544-92-3 copper(I) cyanide 
• 68-12-2 N,N-dimethyl-formamide 
• 364-74-9 1,4-difluoro-2-nitrobenzene 
• 446-09-3 2-bromo-5-fluoronitrobenzene 

Downstream Products

• 38469-83-9 4-methoxy-2-nitro-benzonitrile 
• 1189352-72-4 2-(2-nitro-4-pyrrolidin-1-ylphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol 
• 1189352-74-6 2-(2-amino-4-pyrrolidin-1-ylphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol 
• 1189352-73-5 2-(7-methoxy-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-5-pyrrolidin-1-ylaniline 
• 1189353-72-7 2-nitro-4-pyrrolidin-1-ylbenzenecarbothioamide 
• 1189353-74-9 2-amino-4-pyrrolidin-1-ylbenzenecarbothioamide 
• 1189353-73-8 2-amino-4-pyrrolidin-1-ylbenzonitrile 
• 1260539-10-3 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile 
• 1260539-09-0 2-Amino-4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide 
• 1189353-71-6 2-nitro-4-pyrrolidin-1-ylbenzonitrile 
• 507239-68-1 4-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-ylmethoxy)-2-nitro-benzonitrile 
• 446-32-2 4-fluoroanthranilic acid 
• 394-01-4 4-fluoro-2-nitrobenzoic acid 
• 80517-65-3 2-Chloro-5-(4-fluoro-2-isocyanato-benzyl)-thiophene 

Relevant articles and documents

Conversions of aryl carboxylic acids into aryl nitriles using multiple types of Cu-mediated decarboxylative cyanation under aerobic conditions

Here, we used malononitrile or AMBN as a cyanating agent to develop efficient and practical protocols for Cu-mediated decarboxylative cyanations, under aerobic conditions, of aryl carboxylic acids bearing nitro and methoxyl substituents at the ortho position as well as of heteroaromatic carboxylic acids. These protocols involved economical methods to synthesize value-added aryl nitriles from simple and inexpensive raw materials. Further diversification of the 2-nitrobenzonitrile product was performed to highlight the practicality of the protocols. This journal is

Method for synthesizing aryl cyanide by taking aryl carboxylic acid as raw material

The invention discloses a method for synthesizing aryl cyanide by taking aryl carboxylic acid as a raw material, which is characterized in that aryl cyanide is synthesized by taking aryl carboxylic acid as a raw material, taking a combination of NH4X and N, N-dimethylformamide as a cyanide source and taking silver sulfate and copper acetate as catalysts under the action of acid and oxygen. Compared with a conventional aryl cyanide synthesis method, the method disclosed by the invention has the advantages that reaction raw materials (aryl carboxylic acid, NH4X and N, N-dimethylformamide) are cheap and easy to obtain, and the dosage of a metal catalyst is small; meanwhile, oxygen is used as an oxidizing agent, so that the method has the obvious advantages of small environmental pollution, good tolerance to various functional groups on an aromatic ring, high yield and the like; the method disclosed by the invention can be widely applied to synthesis of medicines, functional materials, natural products and other fields in the industry and academic circles.

A preparation method for 4-methoxy-2-nitrobenzoic acid

An industrial preparation method for 4-methoxy-2-nitrobenzoic acid is disclosed. In the method, p-difluorobenzene is adopted as an initial raw material and subjected to nitration, ammonolysis, diazotization bromination, cyaniding, methoxylation and hydrolysis which are six steps to synthesize the 4-methoxy-2-nitrobenzoic acid. The 4-methoxy-2-nitrobenzoic acid obtained by the method is white powdered solid with purity being 98.5%, the raw material conversion ratio in each step is 100%, and the total yield of the whole process is 35.8%.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

Tetramethylammonium chloride as a selective and robust phase transfer catalyst in a solid-liquid halex reaction: The role of water

Tetramethylammonium chloride (TMAC) is an effective phase transfer catalyst for the selective chloride/fluoride exchange reaction of activated aryl chlorides with potassium fluoride provided that the amount of water in the system is limited and controlled.

FLUORINATED TRICYCLIC NEUROLEPTICS WITH PROLONGED ACTION: DERIVATIVES AND ANALOGUES OF 2-(4-(7-FLUORO-2-ISOPROPYL-10,11-DIHYDRODIBENZOTHIEPIN-11-YL)PIPERAZINE-1-YL)ETHANOL

The preparation of 4-fluoro-2-nitrobenzonitrile (V), an intermediate in the synthesis of the title compound I, from 4-fluoro-2-nitroaniline via 5-fluoro-2-iodonitrobenzene (VII) was elaborated.Syntheses of 1,1,1,3,3,3-hexadeutero-2-propyl (XX) and 1,3,4-trideutero (XXVIII) analogues of compound I from hexadeuteroacetone, and pentadeuterobromobenzene, respectively, were carried out.Compound I was esterified with acetic anhydride, decanoic acid and 3,4,5-trimethoxybenzoyl chloride to give the esters II-IV.Acylation of compound XXX with acetyl chloride, 4-fluorophenoxyacetyl chloride and (4-fluorophenylthio)acetyl chloride and the following reduction of the amides with lithium aluminium hydride gave compounds XXXII, XXXIX, and XL.Substitution reactions of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzothiepin with the corresponding N-monosubstituted piperazines resulted in compounds XXXIII-XXXV, XXXVII, XXXVIII, XLI and XLII.Alkylation of XXX with 2-(2-chloroethyl)-1,3-dioxolane afforded compound XXXVI.Pharmacological testing of the new compounds, derivatives and analogues of the neuroleptic agent isofloxythepin (I), for discoordinating and cataleptic activities, showed especially for compounds II, XXXIV and XXXVI very intensive and long-lasting effects.The decanoate III has properties of a depot neuroleptic agent.

FLUORINATED TRICYCLIC NEUROLEPTICS WITH PROLONGED ACTION: 7-FLUORO-11--2-ISOPROPYL-10,11-DIHYDRODIBENZOTHIEPIN

Substitution reaction of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzothiepin with 1-(2-hydroxyethyl)piperazine gave the title compound I which proved a very potent and long acting oral neuroleptic agent ("isofloxythepin").Its resolution by means of dibenzoyl-(+)- and (-)-tartaric acid led to (-)- and (+)-enantiomer out of which the former represents the neuroleptically active component.In the synthetic sequence leading to I, preparation of two key intermediates was re-elaborated using new partial sequences: 4-fluoro-2-iodobenzoic acid (XIII) from 4-fluoro-2-nitroaniline (V) via the nitrile VI and the acids VIII and XII, and acetic acid (XVIII) from XIII via XIV and the compounds XV-XVII.The sulfoxides and N-oxides XIX-XXII were prepared as potential metabolites of isofloxithepin (I).