13589-72-5

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-HYDROXYBENZONITRILE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of drugs with specific therapeutic properties, making it a valuable building block in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 5-CHLORO-2-HYDROXYBENZONITRILE is utilized as a precursor in the production of pesticides. Its chemical properties enable the creation of effective pest control agents, contributing to agricultural productivity and crop protection.
Used as a Precursor for Complex Organic Molecules:
5-CHLORO-2-HYDROXYBENZONITRILE is also employed as an important precursor for the synthesis of complex organic molecules. Its reactivity and functional groups make it suitable for further chemical reactions, leading to the formation of advanced organic compounds with diverse applications.
It is crucial to handle and store 5-CHLORO-2-HYDROXYBENZONITRILE with caution, as it may pose hazards if not used or managed properly, ensuring safety in both research and industrial settings.

InChI:InChI=1/C7H4ClNO/c8-6-1-2-7(10)5(3-6)4-9/h1-3,10H

Upstream product

• 556-64-9 methyl thiocyanate 
• 106-48-9 4-chloro-phenol 
• 87974-49-0 (E)-5-chloro-2-hydroxybenzaldehyde oxime 
• 39900-62-4 5-chlorobenzo[d]isoxazole 
• 87974-49-0 5-chloro-2-hydroxy-benzaldehyde oxime 
• 611-20-1 salicylonitrile 
• 635-93-8 5-chlorosalicyclaldehyde 
• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 695-96-5 2-bromo-4-chlorophenol 
• 144-55-8 sodium hydrogencarbonate 
• 71643-66-8 4-chloro-2-iodo phenol 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 17200-29-2 5-chloro-benzoxazole 
• 198902-28-2 2-(acetyloxy)-5-chlorobenzonitrile 

Downstream Products

• 611-20-1 salicylonitrile 
• 3958-77-8 cyanobenzo-1,4-quinone 
• 4640-29-3 2,5-dihydroxyphenylcyanide 
• 40530-18-5 5-bromo-2-hydroxybenzonitrile 
• 331729-12-5 2-cyano-4-chlorophenoxyacetic acid tert-butyl ester 
• 403825-98-9 5-(4-chloro-2-cyanophenoxy)pentanoic acid 
• 913722-86-8 5-chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrile 
• 913722-91-5 (2S)-3-(3-[(2R)-3-(4-chloro-2-cyanophenoxy)-2-hydroxypropoxy]phenyl)-2-isopropoxypropionic acid ethyl 
• 331729-65-8 2-(benzyloxy)-5-chlorobenzonitrile 
• 781604-57-7 (2-(benzyloxy)-5-chlorophenyl)methanamine 

Relevant academic research and scientific papers

Modulation of imprinting efficiency in nanogels with catalytic activity in the Kemp elimination

The interactions between the template and the functional monomer are a key to the formation of cavities in the imprinted nanogels with high molecular recognition properties. Nanogels with enzyme-like activity for the Kemp elimination have been synthesized

On the magnitude and specificity of medium effects in enzyme-like catalysts for proton transfer

Medium effects are normally studied by comparing the rates of reactions in different solvents. However, medium effects at the active site of enzymes differ dramatically from bulk solvents, both in their diversity (the presence of more than one type of "so

Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands

We describe a general and efficient protocol for the synthesis of organophosphine compounds from phenols and phosphines (R2PH) via a metal-free C-O bond cleavage and C-P bond formation process. This approach exhibits broad substrate scope and excellent functional group tolerance. The synthetic utilities of this protocol were demonstrated by the synthesis of chiral ligands via the various transformations of cyano groups and their applications in asymmetric catalysis.

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

Preparation method of piperidine compound

The invention discloses a preparation method of a piperidine compound 4-((2-(aminomethyl)-4-bromophenoxy) methyl) piperidine-1-tert-butyl formate. 5-chloro-2-hydroxybenzaldehyde is used as a starting material and subjected to oximation, elimination, ether

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes

A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the

HCV PROTEASE INHIBITORS

The present invention discloses a compound of general formula (I); A is O, S, CH, NH or NR', when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C-Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or -Y1-Rm; A1 is NH or CH2; R1' is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalky etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.