20143-41-3

Basic information

• Product Name: (2-chlorophenoxy)acetyl chloride
• Synonyms: (2-chlorophenoxy)acetyl chloride;acetyl chloride, (2-chlorophenoxy)-;2-(2-chlorophenoxy)acetyl chloride;2-(2-chlorophenoxy)ethanoyl chloride
• CAS NO: 20143-41-3
• Molecular Formula: C₈H₆Cl₂O₂
• Molecular Weight: 205.03804
• Mol File: 20143-41-3.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2-chlorophenoxy)acetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2-chlorophenoxy)acetyl chloride(20143-41-3)
• EPA Substance Registry System: (2-chlorophenoxy)acetyl chloride(20143-41-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20143-41-3(Hazardous Substances Data)

Usage

Description

(2-chlorophenoxy)acetyl chloride, also known as 2-Chloroacetoxybenzoyl chloride, is a chemical compound with the formula C8H6Cl2O3. It is a colorless liquid that is commonly used as a chemical intermediate in the production of agrochemicals, pharmaceuticals, and other organic compounds. The presence of both the acetyl and chlorophenoxy functional groups makes it a versatile building block for the synthesis of a wide range of chemical structures.

Uses

Used in Agrochemical Industry:
(2-chlorophenoxy)acetyl chloride is used as a chemical intermediate for the production of herbicides and plant growth regulators. Its versatile functional groups allow for the synthesis of various agrochemical compounds that can effectively control or promote plant growth.
Used in Pharmaceutical Industry:
(2-chlorophenoxy)acetyl chloride is used as a building block in the synthesis of pharmaceuticals such as anti-inflammatories and anti-cancer drugs. Its unique structure enables the development of new and effective medications for various health conditions.
However, it is important to handle this chemical with caution, as it is corrosive and harmful if ingested or inhaled, and can cause severe skin and eye irritation. Proper safety measures should be taken during its production, storage, and use to minimize potential risks.

Upstream product

• 614-61-9 (2-chlorophenoxy)acetic acid 
• 95-57-8 2-monochlorophenol 
• 35535-81-0 sodium 2-chlorophenoxide 
• 36304-23-1 tert-butyl 2-(2-chlorophenoxy)acetate 
• 6956-85-0 Methyl (2-chlorophenoxy)acetate 

Downstream Products

• 115917-05-0 (2-chloro-phenoxy)-acetic acid-(3-oxo-androst-4-en-17β-yl ester) 
• 62095-50-5 (2-chloro-phenoxy)-acetic acid phenyl ester 
• 497087-21-5 N-[(2-chloro-phenoxy)-acetyl]-sulfanilic acid amide 
• 855602-42-5 (2-chloro-phenoxy)-ketene 
• 72192-83-7 3-(2-chloro-phenoxy)-4-(4-methoxy-phenyl)-1-(4-p-tolyl-thiazol-2-yl)-azetidin-2-one 
• 72192-70-2 3-(2-chloro-phenoxy)-4-(2-hydroxy-phenyl)-1-(4-phenyl-thiazol-2-yl)-azetidin-2-one 
• 72192-80-4 3-(2-chloro-phenoxy)-4-(2-hydroxy-phenyl)-1-(4-p-tolyl-thiazol-2-yl)-azetidin-2-one 
• 72192-93-9 3-(2-chloro-phenoxy)-1-(5-methyl-4-phenyl-thiazol-2-yl)-4-(4-nitro-phenyl)-azetidin-2-one 
• 64994-69-0 5-[(2-chloro-phenoxy)-acetyl]-2-(4-methoxy-phenyl)-5H-oxazolo[4,5-b]phenoxazine 
• 72192-37-1 2-(2-chloro-phenoxy)-N-(4-phenyl-thiazol-2-yl)-acetamide 
• 72192-61-1 2-(2-chloro-phenoxy)-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 72192-43-9 2-(2-chloro-phenoxy)-N-(4-p-tolyl-thiazol-2-yl)-acetamide 
• 72192-73-5 3-(2-chloro-phenoxy)-4-(4-methoxy-phenyl)-1-(4-phenyl-thiazol-2-yl)-azetidin-2-one 
• 75057-59-9 6,7-dibromo-2-(2-chloro-phenoxymethyl)-benzo[d][1,3]oxazin-4-one 

Relevant articles and documents

Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Identification of potent and selective small molecule inhibitors of the cation channel TRPM4

Background and Purpose: TRPM4 is a calcium-activated non-selective cation channel expressed in many tissues and implicated in several diseases, and has not yet been validated as a therapeutic target due to the lack of potent and selective inhibitors. We sought to discover a novel series of small-molecule inhibitors by combining in silico methods and cell-based screening assay, with sub-micromolar potency and improved selectivity from previously reported TRPM4 inhibitors. Experimental Approach: Here, we developed a high throughput screening compatible assay to record TRPM4-mediated Na+ influx in cells using a Na+-sensitive dye and used this assay to screen a small set of compounds selected by ligand-based virtual screening using previously known weakly active and non-selective TRPM4 inhibitors as seed molecules. Conventional electrophysiological methods were used to validate the potency and selectivity of the hit compounds in HEK293 cells overexpressing TRPM4 and in endogenously expressing prostate cancer cell line LNCaP. Chemical chaperone property of compound 5 was studied using Western blots and electrophysiology experiments. Key Results: A series of halogenated anthranilic amides were identified with TRPM4 inhibitory properties with sub-micromolar potency and adequate selectivity. We also showed for the first time that a naturally occurring variant of TRPM4, which displays loss-of-expression and function, is rescued by the most promising compound 5 identified in this study. Conclusions and Implications: The discovery of compound 5, a potent and selective inhibitor of TRPM4 with an additional chemical chaperone feature, revealed new opportunities for studying the role of TRPM4 in human diseases and developing clinical drug candidates.