13589-72-5

Basic information

• Product Name: 5-CHLORO-2-HYDROXYBENZONITRILE
• Synonyms: 5-CHLORO-2-HYDROXYBENZONITRILE;AKOS B029245;5-Chloro-2-hydroxybenzonitrile, tech;4-Chloro-2-cyanophenol;4-Chloro-2-cyanophenol, 5-Chlorosalicylonitrile;Benzonitrile, 5-chloro-2-hydroxy-;2-Hydroxy-5-chlorobenzonitrile;5-Chlorosalicylonitrile
• CAS NO: 13589-72-5
• Molecular Formula: C₇H₄ClNO
• Molecular Weight: 153.57
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 13589-72-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 152-154°C
• Boiling Point: 269.4 °C at 760 mmHg
• Flash Point: 116.7 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0.00438mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.72±0.18(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-HYDROXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-HYDROXYBENZONITRILE(13589-72-5)
• EPA Substance Registry System: 5-CHLORO-2-HYDROXYBENZONITRILE(13589-72-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• Hazardous Substances Data: 13589-72-5(Hazardous Substances Data)

Usage

Description

5-CHLORO-2-HYDROXYBENZONITRILE, with the molecular formula C7H4ClNO, is a nitrile derivative characterized by the presence of a chloro and hydroxyl group attached to a benzene ring. This chemical compound serves as a versatile intermediate in the synthesis of a variety of organic compounds, particularly in the pharmaceutical and agrochemical sectors.

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

• 106-48-9 4-chloro-phenol 
• 545-06-2 trichloroacetonitrile 
• 198902-28-2 2-(acetyloxy)-5-chlorobenzonitrile 
• 71643-66-8 4-chloro-2-iodo phenol 
• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 695-96-5 2-bromo-4-chlorophenol 
• 144-55-8 sodium hydrogencarbonate 
• 87974-49-0 5-chloro-2-hydroxy-benzaldehyde oxime 
• 611-20-1 salicylonitrile 
• 635-93-8 5-chlorosalicyclaldehyde 
• 87974-49-0 (E)-5-chloro-2-hydroxybenzaldehyde oxime 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 17200-29-2 5-chloro-benzoxazole 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 38541-71-8 Thiophosphoric acid O-(4-chloro-2-cyano-phenyl) ester O'-ethyl ester S-propyl ester 
• 106-48-9 4-chloro-phenol 
• 7120-43-6 5-chlorosalicylamide 
• 331728-87-1 2-aminomethyl-4-chlorophenoxyacetic acid tert-butyl ester 
• 331728-61-1 (2R,3R,4S,5S)(2-{[9-(4-azido-3-hydroxy-5-methylcarbamoyl-tetrahydrofuran-2-yl)-9H-purin-6-ylamino]-methyl}-4-chlorophenoxy)acetic acid 
• 331728-62-2 (2R,3R,4S,5S)(2-{[9-(4-azido-3-hydroxy-5-methylcarbamoyl-tetrahydrofuran-2-yl)-9H-purin-6-ylamino]-methyl}-4-chlorophenoxy)acetic acid tert-butyl ester 
• 331728-58-6 (2S,3S,4R,5R)3-azido-5-{6-[5-chloro-2-(2-oxo-2-piperazin-1-yl-ethoxy)-benzylamino]-purin-9-yl}-4-hydroxy-tetrahydro-furan-2-carboxylic acid methylamide 
• 118872-77-8 5-chloro-2-hydroxy-benzamidrazone 
• 478374-01-5 {4'-Methoxy-3'-[3-(4-chloro-2-cyanophenoxy)-1-propynyl]biphenyl-3-yl}acetic acid 
• 478374-14-0 {3'-[2-Hydroxy-3-(4-chloro-2-cyanophenoxy)propoxy]-4'-methoxybiphenyl-3-yl}acetic acid 
• 478374-28-6 {4'-[3-(4-Chloro-2-cyanophenoxy)-1-propynyl]biphenyl-3-yl}acetic acid 
• 478374-47-9 {4'-[2-Hydroxy-3-(4-chloro-2-cyanophenoxy)propoxy]biphenyl-3-yl}acetic acid 
• 403825-98-9 5-(4-chloro-2-cyanophenoxy)pentanoic acid 
• 913722-86-8 5-chloro-2-[[(2S)-2-hydroxy-3-(trityloxy)propyl]oxy]benzonitrile 

Relevant articles and documents

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

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.

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.

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.