13073-27-3

Usage

Uses

Used in Pharmaceutical Industry:
3-chloro-2-hydroxybenzonitrile is utilized as an intermediate in the synthesis of various pharmaceuticals. Its chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-chloro-2-hydroxybenzonitrile is employed as an intermediate for the production of insecticides and herbicides. Its antimicrobial and antifungal properties make it a valuable asset in creating effective pest control solutions for agricultural applications.
Used in Dye Manufacturing:
3-chloro-2-hydroxybenzonitrile is used in the manufacturing of dyes, where its chemical properties contribute to the creation of a diverse range of colorants for various industries, including textiles and plastics.
Used in Flavoring and Fragrance Industry:
3-chloro-2-hydroxybenzonitrile also finds application in the production of flavoring agents and other fragrance compounds, where it helps in creating unique scents and tastes for various consumer products.
Safety Note:
It is important to handle 3-chloro-2-hydroxybenzonitrile with care due to its potential harmful effects if ingested, inhaled, or absorbed through the skin. Proper safety measures should be taken to minimize risks during its use and production.

Upstream product

• 65685-54-3 7-chloro-benzo[d]isoxazole 
• 50-00-0 formaldehyd 
• 95-57-8 2-monochlorophenol 
• 611-20-1 salicylonitrile 
• 1927-94-2 3-chlorosalicylaldehyde 

Downstream Products

• 64037-11-2 7-chlorobenzo[d]oxazol-2-amine 

Relevant academic research and scientific papers

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.

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.

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

A one-pot synthesis of substituted salicylnitriles

Phenols were converted to salicylaldehydes with paraformaldehyde, MgCl2-Et3N in THF, and subsequent treatment with aqueous ammonia gave the corresponding imines which were oxidized with IBX to the desired salicylnitriles. The sequence of reactions was conveniently carried out as a one-pot procedure under mild conditions.