345-17-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5-fluoronitrobenzene is used as a key intermediate in the synthesis of N,N-dimethyl-2-(2-amino-4-fluorophenylthio)benzylamine, a compound with potential pharmaceutical applications. Its unique structure allows for the development of new drugs with improved therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2-chloro-5-fluoronitrobenzene is used as a starting material for the preparation of N-methyl-2-(2-amino-4-fluorophenylthio)benzylamine. 2-CHLORO-5-FLUORONITROBENZENE can be further modified and functionalized to create a variety of organic molecules with diverse applications in various industries.

InChI:InChI=1/C6H3ClFNO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H

Upstream product

• 352-33-0 1-Chloro-4-fluorobenzene 
• 371-40-4 4-fluoroaniline 
• 394-01-4 4-fluoro-2-nitrobenzoic acid 
• 351-83-7 4'-fluoroacetanilide 
• 448-39-5 N-(4-fluoro-2-nitrophenyl)acetamide 
• 364-78-3 2-nitro-4-fluoroaniline 

Downstream Products

• 28340-62-7 4-(dimethylamino)-2-nitrobenzonitrile 
• 131105-89-0 2-amino-4-fluorobenzene-1-thiol 
• 452-83-5 2-chloro-5-fluoroaniline 
• 606937-74-0 2-[(4-fluoro-2-nitrophenyl)thio]-N,N-dimethylbenzamide 
• 1065678-31-0 5-Fluoro-3H-1,3-benzothiazol-2-one 
• 1424386-52-6 1-(2-amino-3-chloro-6-fluorophenyl)naphthalen-2-ol 
• 1629-93-2 5-fluoro-2-phenyl-1,3-benzothiazole 
• 872726-44-8 NSC 721648 
• 107618-21-3 4-(2-amino-4-fluoro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 
• 107618-33-7 4-(5-fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester 
• 58859-77-1 5-fluoro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one 
• 1301190-11-3 1,1-dimethylethyl (3S)-3-{[(4-fluoro-2-nitrophenyl)amino]methyl}-1-pyrrolidinecarboxylate 
• 107618-14-4 4-(4-fluoro-2-nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 
• 130131-24-7 5-Fluoro-2-(2-imino-thiazolidin-3-yl)-phenylamine; compound with ethanesulfonic acid 

Relevant academic research and scientific papers

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions

Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.

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.

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).