3586-15-0

Basic information

• Product Name: 3-PHENOXYBENZOYL CHLORIDE
• Synonyms: 3-PHENOXYBENZOYL CHLORIDE;3-Phenoxybenzoyl chloride 97%;3-Phenoxybenzoylchloride97%
• CAS NO: 3586-15-0
• Molecular Formula: C₁₃H₉ClO₂
• Molecular Weight: 232.66
• Mol File: 3586-15-0.mol

Chemical Properties

• Boiling Point: 174 °C
• Flash Point: 122.4 °C
• Appearance: /
• Density: 1.247g/cm³
• Vapor Pressure: 0.000171mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 3-PHENOXYBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENOXYBENZOYL CHLORIDE(3586-15-0)
• EPA Substance Registry System: 3-PHENOXYBENZOYL CHLORIDE(3586-15-0)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 3586-15-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenoxybenzoyl chloride is used as an intermediate for the manufacturing of active pharmaceutical ingredients. It contributes to the development of new drugs by providing a versatile chemical structure that can be modified to achieve desired therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Phenoxybenzoyl chloride serves as a key intermediate in the synthesis of pesticides. Its reactivity and structural properties allow for the creation of effective compounds that protect crops from pests and diseases.
Used in Organic Synthesis:
3-Phenoxybenzoyl chloride is utilized as a reagent in organic synthesis, enabling chemists to construct complex organic molecules through various chemical reactions. Its presence in the reaction mixture facilitates the formation of desired products, expanding the scope of organic chemistry.
Used in Dye Production:
3-Phenoxybenzoyl chloride is employed in the production of dyes, where its chemical properties contribute to the creation of vibrant and stable colorants used in various industries, such as textiles, plastics, and printing inks.
Used in Perfumery:
In the perfume industry, 3-Phenoxybenzoyl chloride is used in the synthesis of fragrances. Its ability to form stable and aromatic compounds makes it a valuable component in the creation of long-lasting and complex scents.
Used in Fine Chemicals Production:
3-Phenoxybenzoyl chloride also finds application in the production of fine chemicals, which are high-purity chemicals used in various specialized applications, such as research, analytical chemistry, and the synthesis of high-value compounds.
Overall, 3-Phenoxybenzoyl chloride is an indispensable chemical in the field of organic chemistry, with a diverse range of industrial and research applications that extend across multiple industries.

InChI:InChI=1/C13H9ClO2/c14-13(15)10-5-4-8-12(9-10)16-11-6-2-1-3-7-11/h1-9H

Upstream product

• 50789-43-0 methyl 3-phenoxybenzoate 
• 108-39-4 3-methyl-phenol 
• 108-90-7 chlorobenzene 
• 60677-14-7 ethyl 3-phenoxybenzoate 
• 7781-98-8 ethyl-3-hydroxybenzoate 
• 3739-38-6 3-phenoxybenzoic acid 
• 79-37-8 oxalyl dichloride 
• 108-95-2 phenol 
• 3586-12-7 3-phenoxyaniline 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 50789-45-2 3-phenoxybenzonitrile 
• 3586-14-9 3-phenoxytoluene 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 

Downstream Products

• 65261-20-3 N-(2-Methoxy-ethyl)-3-phenoxy-benzamide 
• 65261-18-9 N-(2-Methyl-allyl)-3-phenoxy-benzamide 
• 57991-36-3 3-phenoxybenzoic acid-glycine conjugate 
• 1173295-09-4 ethyl 3-phenoxybenzoylcyanoacetate 
• 1094491-62-9 C₄₈H₆₂N₄O₂₂ 
• 1044872-95-8 N-(3-phenoxybenzoyl)-5,8-dichloro-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044872-94-7 N-(3-phenoxybenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 73258-84-1 3-phenoxybenzamide 
• 75-00-3 chloroethane 
• 177711-40-9 3-(3-phenoxybenzoyl)-1phenyl-imidazolidin-2,4-dione 
• 149609-00-7 N-hydroxy-N-[2-(((1-(4-chlorophenylmethyl)pyrrol-2-yl)carbonyl)amino)ethyl]urea 
• 313347-53-4 N₁-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-phenoxybenzamide 
• 13826-35-2 3-Phenoxybenzyl alcohol 
• 63935-57-9 sodium hydroxy(3-phenoxyphenyl)methanesulfonate 

Relevant articles and documents

Uptake and transformation of pesticide metabolites by duckweed (Lemna gibba)

Uptake and transformation of 14C-labeled metabolites from several pesticides, 3-methyl-4-nitrophenol (1), 3,5-dichloroaniline (2), 3-phenoxybenzoic acid (3), (R,S)-2-(4-chlorophenyl)-3-methylbutanoic acid (4), and (1RS)-trans-3-(2,2-dichlorovin

Design and synthesis of N-(3-sulfamoylphenyl)amides as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

The protozoan parasite Trypanosoma brucei (T. brucei) causes human African trypanosomiasis (HAT), which is a fatal and neglected disease in the tropic areas, and new treatments are urgently needed. Leucyl-tRNA synthetase (LeuRS) is an attractive target for the development of antimicrobial agents. In this work, starting from the hit compound thiourea ZCL539, we designed and synthesized a series of amides as effective T. brucei LeuRS (TbLeuRS) synthetic site inhibitors. The most potent compounds 74 and 91 showed IC50 of 0.24 and 0.25 μM, which were about 700-fold more potent than the starting hit compound. The structure-activity relationship was also discussed. These compounds provided a new scaffold and lead compounds for further development of antitrypanosomal agents.

Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst

A Ni-catalyzed decarbonylative methylation of aromatic esters was achieved using methylaluminums as methylating agents. Dimethylaluminum chlorides uniquely worked as the methyl source. Because of the Lewis acidity of aluminum reagents, less reactive alkyl esters could also undergo the present methylation. By controlling the Lewis acidity of aluminum reagents, a chemoselective decarbonylative cross-coupling between alkyl esters and phenyl esters was successful.

Rational Drug Design of Topically Administered Caspase 1 Inhibitors for the Treatment of Inflammatory Acne

The use of an interleukin β antibody is currently being investigated in the clinic for the treatment of acne, a dermatological disorder affecting 650M persons globally. Inhibiting the protease responsible for the cleavage of inactive pro-IL1β into active IL-1β, caspase-1, could be an alternative small molecule approach. This report describes the discovery of uracil 20, a potent (38 nM in THP1 cells assay) caspase-1 inhibitor for the topical treatment of inflammatory acne. The uracil series was designed according to a published caspase-1 pharmacophore model involving a reactive warhead in P1 for covalent reversible inhibition and an aryl moiety in P4 for selectivity against the apoptotic caspases. Reversibility was assessed in an enzymatic dilution assay or by using different substrate concentrations. In addition to classical structure-activity-relationship exploration, topical administration challenges such as phototoxicity, organic and aqueous solubility, chemical stability in solution, and skin metabolic stability are discussed and successfully resolved.

REDUCTION OF PRO-INFLAMMATORY HDL USING A LEUKOTRIENE INHIBITOR

A method involving the administration of a therapeutically effective amount of a leukotriene inhibitor, a pharmaceutically acceptable salt, a pharmaceutically acceptable N-oxide, a pharmaceutically active metabolite, a pharmaceutically acceptable prodrug, or pharmaceutically acceptable solvate thereof to a human for reducing a level of pro-inflammatory HDL in the human. Various examples of leukotriene inhibitors, including 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin- 3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2, 2-dimethyl-propionic acid, are disclosed for administration for the reduction of pro-inflammatory HDL in a human. Reduction of pro-inflammatory HDL by the leukotriene inhibitor may include conversion of at least a portion of pro-inflammatory HDL to anti-inflammatory HDL.

Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus

A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound 3 that carries an aminoguanidine functionality from one side and a n-butyl moiety on the other ring, several analogues were prepared. Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analogue 21n as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of 21n was confirmed in?vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics.

Design, synthesis, and biological evaluation of oxazolidone derivatives as highly potent N-acylethanolamine acid amidase (NAAA) inhibitors

N-Acylethanolamine-hydrolyzing acid amidase (NAAA) is a lysosomal enzyme that catalyzes the hydrolysis of endogenous fatty acid ethanolamides (FAEs), such as N-palmitoylethanolamide (PEA). PEA exhibits anti-inflammatory and analgesic activities by engaging peroxisome proliferator-activated receptor α (PPAR-α). Preventing PEA degradation by inhibition of NAAA has been proposed as a novel strategy for the treatment of inflammation and pain. In the present study, we reported the discovery of the oxazolidone derivative as a novel scaffold for NAAA inhibitors, and studied the structure-activity relationship (SAR) by modification of the side chain and terminal lipophilic substituents. The results showed that the link chain length of C5, straight and saturated linkages were the preferred shape patterns for NAAA inhibition. Several nanomolar NAAA inhibitors were described, including 2f, 3h, 3i and 3j with IC50 values of 270 nM, 150 nM, 100 nM and 190 nM, respectively. Enzymatic degradation studies suggested that 2f inhibited NAAA in a selective, noncompetitive and reversible pattern. Moreover, 2f showed high anti-inflammatory and analgesic activities after systemic and oral administration.

RhIII-Catalyzed C-H Allylation of Amides and Domino Cycling Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones with N-Bromosuccinimide

A RhIII-catalyzed C-H allylation of electron-deficient arenes, heteroarenes, and alkenes at room temperature was developed with allyl bromide. The reaction was carried out in diethyl ether without dehydration, and C-H activation was assisted by the directing anionic nitrogen of the aniline-derived amide. Following the allylation, a domino cycling synthesis of 3,4-dihydroisoquinolin-1(2H)-ones with N-bromosuccinimide (NBS) through intramolecular aminobromination of the introduced double bond was achieved. A C-H allylation of amides with allyl halides at room temperature and a tandem synthesis of 3,4-dihydroisoquinolin-1(2H)-ones with N-bromosuccinimide (NBS) are reported.

An efficient method for the preparation of hydroxamic acids

Reactions of acyl chlorides with hydroxylamine hydrochloride and NaHCO 3 generate the corresponding hydroxamic acid products in ethyl acetate and water at room temperature for 5 min. This is a simple and efficient method to synthesize a wide range of hydroxamic acids from carboxylic acids in excellent yield and high purity after simple post-treatment without chromatographic purification. In this process, the highlights are the simple separation of products and cheaply available reagents.

Optimizing small molecule inhibitors of calcium-dependent protein kinase 1 to prevent infection by toxoplasma gondii

Toxoplasma gondii is sensitive to bulky pyrazolo [3,4-d] pyrimidine (PP) inhibitors due to the presence of a Gly gatekeeper in the essential calcium dependent protein kinase 1 (CDPK1). Here we synthesized a number of new derivatives of 3-methyl-benzyl-PP (3-MB-PP, or 1). The potency of PP analogues in inhibiting CDPK1 enzyme activity in vitro (low nM IC50 values) and blocking parasite growth in host cell monolayers in vivo (low μM EC 50 values) were highly correlated and occurred in a CDPK1-specific manner. Chemical modification of the PP scaffold to increase half-life in the presence of microsomes in vitro led to identification of compounds with enhanced stability while retaining activity. Several of these more potent compounds were able to prevent lethal infection with T. gondii in the mouse model. Collectively, the strategies outlined here provide a route for development of more effective compounds for treatment of toxoplasmosis and perhaps related parasitic diseases.