14062-24-9

Usage

Chemical Properties

Colorless low melting solid

InChI:InChI=1/C10H11ClO2/c1-2-13-10(12)7-8-3-5-9(11)6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 1878-66-6 4-chlorophenylacetic Acid 
• 64-17-5 ethanol 
• 35453-07-7 2-(p-Chlorphenyl)-1-methylsulfinyl-1-methylthio-ethylen 
• 41904-25-0 1-Phenylsulfinyl-1-methylthio-2-(p-chlor-phenyl)-ethylen 
• 106-39-8 bromochlorobenzene 
• 681-94-7 ethyl 2-(tributylstannyl)acetate 
• 201230-82-2 carbon monoxide 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 124-41-4 sodium methylate 
• 209912-24-3 1-[2-(4-chlorophenyl)ethynyl]-1H-benzotriazole 
• 314765-27-0 (E)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-chlorophenyl)ethenyl trifluoromethanesulfonate 
• 361379-15-9 (Z)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-chlorophenyl)ethenyl trifluoromethanesulfonate 
• 1679-18-1 4-Chlorophenylboronic acid 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 69470-44-6 2-(4-chlorophenyl)-N-(2-hydroxyethyl)acetamide 
• 33691-09-7 ethyl α-formyl-4-chlorophenylacetate 
• 67631-83-8 N-(2-Benzylamino-ethyl)-2-(4-chloro-phenyl)-acetamide 
• 107234-80-0 erythro-2-(4-chlorophenyl)-4-cyano-3-phenylbutanoate d'ethyle 
• 10399-10-7 methyl 2-(4-chlorophenyl)-2-methoxyacetate 
• 79309-64-1 ethoxy-(4-chloro-phenyl)-acetic acid ethyl ester 
• 7138-34-3 p-chloromandelic acid 
• 119540-37-3 Ethyl 3-<5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl>-2-(4-chlorophenyl)propanoate 
• 5445-25-0 ethyl 2-bromo-2-(4-chlorophenyl)acetate 
• 13511-29-0 ethyl 2-(4-chlorophenyl)-2-hydroxyacetate 
• 74569-27-0 Ethyl 4-chloro-α-fluorophenylacetate 
• 125575-28-2 2-acetamido-2-(4'-chlorophenyl)acetate d'ethyle 
• 1256479-12-5 (4-Chloro-3-fluoro-phenyl)-acetic acid ethyl ester 
• 188424-98-8 ethyl 2-(4-chloro-2-fluorophenyl)acetate 

Relevant academic research and scientific papers

2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists

A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical.

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

Synthesis and Biological Activity of Anthranilic Diamide Derivatives Incorporating 1,3,4-oxadiazole or Nitrogen-containing Saturated Heterocyclic Moieties

A series of novel anthranilic diamide derivatives incorporating 1,3,4-oxadiazole or nitrogen-containing saturated heterocyclic moieties were synthesized, characterized, and evaluated for bacteriostatic activity against three phytopathogenic bacteria Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (R. solanacearum). The preliminary biological results indicated that most compounds exhibit bacteriostatic activity against three phytopathogenic bacteria. Among these compounds, compounds 6g, 6f, and 6i displayed better antibacterial activity. In the test with concentration of 200 μg/mL, antibacterial activity of compound 6i and 6j was 96%. In particular, the bacteriostatic activity displayed by compound 6h against Xoo is similar to the one displayed by commercial drug bismerthiazol.

Mechanistic studies on gold-catalyzed direct arene c-h bond functionalization by carbene insertion: The coinage-metal effect

The catalytic functionalization of the Csp2-H bond of benzene by means of the insertion of the CHCO2Et group from ethyl diazoacetate (N2= CHCO2Et) has been studied with the series of coinage-metal complexes IPrMCl (IPr = 1,3-bis- (diisopropylphenyl)imidazol-2-ylidene) and NaBArF 4 (BArF 4 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate). For Cu and Ag, these examples constitute the first use of such metals toward this transformation, which also provides ethyl cyclohepta-2,4,6-trienecarboxylate as a byproduct from the so-called Buchner reaction. In the case of methyl-substituted benzenes, the reaction exclusively proceeds onto the aromatic ring, the Csp3-H bond remaining unreacted. A significant coinage-metal effect has been observed, since the gold catalyst favors the formation of the insertion product into the Csp2-H bond whereas copper and silver preferentially induce the formation of the cycloheptatriene derivative. Experimental studies and theoretical calculations have explained the observed selectivity in terms of the formation of a common Wheland intermediate, resembling an electrophilic aromatic substitution, from which the reaction pathway evolves into two separate routes to each product.

POLYCYCLIC PYRAZOLINONE DERIVATIVE AND HERBICIDE COMPRISING SAME AS EFFECTIVE COMPONENT THEREOF

Provided are a polycyclic pyrazolinone derivative indicated by general formula (1) (in the formula, R1, X1, X2, X3, and Y indicate the definitions provided in the Specification) and a herbicide comprising same as effective component thereof.