500011-92-7

Basic information

• Product Name: ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE
• Synonyms: ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE;Ethyl 3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylate
• CAS NO: 500011-92-7
• Molecular Formula: C₁₁H₉BrClN₃O₂
• Molecular Weight: 330.56506
• Mol File: 500011-92-7.mol
• Article Data: 35

Chemical Properties

• Melting Point: 117-118 °C
• Boiling Point: 421.3°C at 760 mmHg
• Flash Point: 208.595°C
• Appearance: /
• Density: 1.672g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.653
• PKA: -2.48±0.29(Predicted)
• CAS DataBase Reference: ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE(500011-92-7)
• EPA Substance Registry System: ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE(500011-92-7)

Safety Data

• Hazardous Substances Data: 500011-92-7(Hazardous Substances Data)

Usage

Description

ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE is a pyrazole derivative with the molecular formula C10H8BrClN3O2. It is a chemical compound that features bromine, chlorine, and carboxylate functional groups, making it a versatile building block in organic synthesis and pharmaceutical research.
Used in Pharmaceutical Research:
ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE is used as a building block for the preparation of novel pyrazole-based compounds with potential biological activities. Its unique structure and functional groups contribute to the development of new drugs with therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE serves as a valuable intermediate for the creation of various chemical entities. Its presence of bromine and chlorine atoms allows for further functionalization and the synthesis of complex organic molecules.
Used in Agrochemical Development:
ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE is also utilized in the development of new agrochemicals. Its potential to form biologically active compounds makes it a candidate for use in the creation of pesticides or other agricultural chemicals to improve crop protection and yield.
Safety Note:
It is crucial to handle ETHYL 3-BROMO-1-(3-CHLOROPYRIDIN-2-YL)-1H-PYRAZOLE-5-CARBOXYLATE with care and adhere to proper safety protocols to minimize health risks associated with its use and storage.

InChI:InChI=1/C11H9BrClN3O2/c1-2-18-11(17)8-6-9(12)15-16(8)10-7(13)4-3-5-14-10/h3-6H,2H2,1H3

Upstream product

• 500011-88-1 ethyl 1-(3-chloropyridin-2-yl)-3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate 
• 500011-86-9 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid 
• 64-17-5 ethanol 
• 500011-95-0 2-(3-chloropyridin-2-yl)-5-hydroxypyrazole-3-carboxylic acid ethyl ester 
• 1520-50-9 but-2-enedioic acid diethyl ester 
• 500011-89-2 ethyl 5-chloro-2-(3-chloropyridin-2-yl)-3,4-dihydro-2H-pyrazole-3-carboxylate 
• 22841-92-5 3-chloro-2(1H)-pyridinone hydrazone 
• 141-05-9 Diethyl maleate 
• 2402-77-9 2,3-dichloro-pyridine 
• 22841-92-5 (3-chloro-2-pyridyl)hydrazine 
• 500011-88-1 2-(3-chloro-pyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylic acid ethyl ester 
• 500011-91-6 5-bromo-2-(3-chloro-pyridin-2-yl)-3,4-dihydro-2H-pyrazole-3-carboxylic acid ethyl ester 

Downstream Products

• 1352547-69-3 C₁₉H₁₅BrCl₂N₆O₂S 
• 1438853-50-9 C₁₉H₁₇BrClN₅OS 
• 1438853-49-6 C₁₇H₁₂BrClIN₅OS 
• 1438853-48-5 C₁₇H₁₂Br₂ClN₅OS 
• 1438853-47-4 C₁₆H₉BrClF₂N₅OS 
• 1352547-42-2 C₁₇H₁₂BrClN₆O₄S 
• 1352547-47-7 C₁₆H₉BrCl₂N₆O₃S 
• 1438853-46-3 C₁₇H₈Br₃ClF₃N₅O₂S 

Relevant articles and documents

Diamides conformationally restricted with central amino acid: Design, synthesis, and biological activities

Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1-aminocyclopropane-1-carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study, 1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L?1 against M. separate and 61.992 mg·L?1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of 1–23 with the target protein, ryanodine receptors.

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.

Preparation method of key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid

The invention discloses a preparation method of a key intermediate of 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method comprises the following steps: by taking 2,3-dichloropyridine as an initial raw material, carrying out a hydrazine hydrate reflux reaction, and then conducting cooling and centrifuging to obtain a 3-chloro-2-pyridyl wet product; then, enabling the 3-chloro-2-pyridyl wet product to react with diethyl maleate and sodium ethoxide to generate 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine; then carrying out bromination reaction on the 2-(3-chloro-2-pyridyl)-5-oxo-3-pyrazolidine and phosphorus oxybromide to produce a 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product; putting the 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester wet product into water, adding sodium persulfate, and carrying out a reaction so as to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid ethyl ester; and conducting hydrolysis in water to obtain 3-bromo-1-(3-chloro-2-pyridyl)-1H-imidazole-5-carboxylic acid. The method can greatly improve the production efficiency and reduce the production cost, and can be directly used for the next reaction without drying treatment.