3598-13-8

Usage

Uses

Used in Agricultural Industry:
2-(4-Chlorophenoxy)acetonitrile is used as a herbicide for the control of broad-leaved and grassy weeds. It acts as a growth regulator, helping to manage unwanted plant growth in agricultural settings.
Used in Pharmaceutical and Agrochemical Synthesis:
2-(4-Chlorophenoxy)acetonitrile is utilized as a key intermediate in the synthesis of various pharmaceutical and agrochemical products, contributing to the development of new compounds with potential applications in medicine and agriculture.
Environmental Considerations:
Due to its toxicity to aquatic organisms and potential long-term environmental effects, 2-(4-Chlorophenoxy)acetonitrile should be handled and disposed of with care to minimize its impact on ecosystems. Proper management and precautions are necessary to ensure the safety of the environment and aquatic life.

InChI:InChI=1/C8H6ClNO/c9-7-1-3-8(4-2-7)11-6-5-10/h1-4H,6H2

Upstream product

• 107-14-2 chloroacetonitrile 
• 106-48-9 4-chloro-phenol 
• 122-88-3 4-Chlorophenoxyacetic acid 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 1679-18-1 4-Chlorophenylboronic acid 
• 590-17-0 cyanomethyl bromide 
• 75-05-8 acetonitrile 
• 61756-69-2 p-chlorophenoxyacetaldoxime 
• 35368-44-6 p-chlorophenoxythioacetamide 
• 43018-72-0 p-chlorophenoxyacetaldehyde 

Downstream Products

• 59104-19-7 2-(4-chloro-phenoxy)-acetamidine; hydrochloride 
• 3598-09-2 <4-Chlorphenoxy>-acetimidsaeureethylester 
• 15485-60-6 5-Dimethylamino-1-<4-chlorphenoxy>-pentanon-(2) 
• 43018-94-6 1-p-Chlorphenoxy-5-diethylamino-pentanon-⁽²⁾ 
• 28769-06-4 2-(4-chlorophenoxy)ethan-1-amine 
• 19450-49-8 2-(4-Chloro-phenoxy)-N-(octahydro-naphthalen-4a-yl)-acetamide 
• 91225-71-7 7-Benzyl-2-(4-chloro-phenoxymethyl)-5,6,7,8-tetrahydro-3H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-one 
• 120627-50-1 (1-Benzyl-5-nitro-1H-indol-4-yl)-acetonitrile 
• 111795-99-4 2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile 
• 128828-70-6 2-(4-Chloro-phenoxymethyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 120627-52-3 (1,2-Dimethyl-5-nitro-1H-indol-4-yl)-acetonitrile 
• 128849-55-8 2-(4-Chloro-phenoxymethyl)-5-methyl-4-oxo-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 91225-91-1 2-(4-Chloro-phenoxymethyl)-3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-one 
• 3598-08-1 Ethyl 2-(4-chlorophenoxy)acetimidate hydrochloride 

Relevant academic research and scientific papers

Synthesis of aryloxyacetonitriles based on arylboronic acids with 2-bromoacetonitrile

A new and efficient protocol for the synthesis of aryloxyacetonitriles based on arylboronic acids with 2-bromoacetonitrile has been developed using eco-friendly hydrogen peroxide as oxidant under metal-free conditions. This method is compatible with arylboronic acid attached sensitive substituent and obtains desired product in moderate to good yield.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

An efficient protocol for facile synthesis of new 5-substituted-1H-tetrazole derivatives using copper-doped silica cuprous sulfate (CDSCS) as heterogeneous nano-catalyst

A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93percent). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.

Perfluorobutyl iodide-assisted direct cyanomethylation of azoles and phenols with acetonitrile

A perfluorobutyl iodide-assisted transition-metal-free cyanomethylation of azoles and phenols with acetonitrile in the presence of NaH has been developed. The reaction proceeded smoothly under mild reaction conditions to give the cyanomethylated products in moderate to high yields. A mechanism involving the cyanomethyl radical through C-H bond cleavage in acetonitrile was proposed. This journal is

Combinatorial synthesis and in vitro evaluation of a biaryl hydroxyketone library as antivirulence agents against mrsa

Antibiotic resistance coupled with decreased development of new antibiotics necessitates the search for novel antibacterial agents. Antivirulence agents offer an alternative to conventional antibiotics. In this work, we report on a family of small-molecule antivirulence agents against methicillin-resistant Staphylococcus aureus (MRSA), the most widespread bacterial pathogen. Structure-activity relationship studies led to the development of a concise synthesis of a 148-member biarylhydroxyketone library. An acylation bond-forming process afforded resorcinols (1) and aryloxy acetonitriles (2) as synthons. A Lewis-acid-activated Friedel-Crafts' acylation step involving a nitrile functionality of 2 by ZnCl2, followed by nucleophilic attack by 1 was executed to obtain biaryl hydroxyketones in excellent yields. A large number of products crystallized. This strategy affords a range of biarylhydroxyketones in a single step. This is the first collective synthetic study documenting access to this class of compounds through a single synthetic operation. In vitro efficacy of compounds in this library was evaluated by a rabbit erythrocyte hemolysis assay. The most efficacious compound, 4f-12, inhibits hemolysis by 98.1 ± 0.1% compared to control in the absence of the compound.

Facile synthesis of nitriles via manganese oxide promoted oxidative dehydrosulfurization of primary thioamides

In the presence of manganese oxides, dehydrosulfurization of various kinds of primary thioamides including aromatic, heterocyclic, and aliphatic ones efficiently proceeded to give the corresponding nitriles in high yields. The observed catalysis was truly heterogeneous, and manganese oxides could be reused.

A new synthesis of 2-aryloxypropionic acids derivatives via selective mono-C-methylation of methyl aryloxyacetates and aryloxyacetonitriles with dimethyl carbonate

A one-pot procedure for the mono-C-methylation of methyl aryloxyacetates and aryloxyaceto nitriles by dimethyl carbonate (DMC) is reported. The reaction is carried out in an autoclave at high temperatures (180-200°C) and in the presence of a base (K2

Synthesis and Antitubercular Activity of 4-(5-Nitro-2-furyl/2-pyrazinyl/1-adamantyl)-2-(alkyl/aryl/arylamino)thiazoles

The reaction of haloketones, obtained from Arndt-Eistert reaction on the acid chlorides of 1-adamantane, 5-nitrofuroic acid and pyrazine-2-carboxylic acid, with different thioamides and thioureas affords the title thiazoles (I-III).Some of them exhibit interesting antitubercular activity at 6.25 to 0.38 μg/ml concentration against H37Rv strain of M. tubercolosis in vitro testing.The structure activity relationship (SAR) has also been discussed.

Composition and process for promoting the growth of crop plants

Compounds of the formula wherein Ar is (substituted) phenyl or naphthyl, X is oxygen, sulfur, SO or SO2, n is 1-3 and R is CN or C(NH2)NOR1, (wherein R1 is preferably hydrogen) are useful as safeners in crop protection.

Method of inhibiting sickling of sickle erythrocytes employing 2-((halophenoxy)methyl)-2-imidazolines

Method for inhibiting the sickling of sickle erythrocytes in blood by contacting the sickle erythrocytes with a compound of the formula: STR1 or a pharmaceutically-acceptable salt thereof, wherein Rm represents hydrogen or alkyl; and Rp/s