22841-92-5

Basic information

• Product Name: (3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE
• Synonyms: (3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE;3-CHLORO-2-HYDRAZINOPYRIDINE;3-Chloro-2-hydrazinopyridine 98%;3-Chloro-2-hydrazinylpyridine;3-chloro-2-hydrazylpyridine;2-(3-chloropyridin-2-yl)hydrazine
• CAS NO: 22841-92-5
• Molecular Formula: C₅H₆ClN₃
• Molecular Weight: 143.57
• Product Categories: blocks;Pyridines;pharmacetical;Heterocycle-Pyridine series;amine|alkyl chloride
• Mol File: 22841-92-5.mol

Chemical Properties

• Melting Point: 165-167°
• Boiling Point: 276.7 °C at 760 mmHg
• Flash Point: 121.1 °C
• Appearance: /
• Density: 1.418 g/cm³
• Vapor Pressure: 0.00474mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 8.65±0.70(Predicted)
• CAS DataBase Reference: (3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: (3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE(22841-92-5)
• EPA Substance Registry System: (3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE(22841-92-5)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 22841-92-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE is used as a building block for the synthesis of pharmaceuticals due to its unique structure and properties that facilitate the creation of new compounds with potential therapeutic applications.
Used in Medicinal Chemistry Research:
(3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE is utilized as a research compound for exploring its interactions with biological targets, which may lead to the discovery of new drugs with specific biological activities.
Used in Antituberculosis Drug Development:
(3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE is considered as a potential anti-tuberculosis agent, making it a promising candidate for the development of new medications to combat tuberculosis, a disease that requires innovative treatment options.
Used in Agricultural and Crop Protection Product Development:
(3-CHLORO-PYRIDIN-2-YL)-HYDRAZINE may also have potential applications in the development of agricultural and crop protection products, indicating its versatility beyond the pharmaceutical sector.

InChI:InChI=1/C5H6ClN3/c6-4-2-1-3-8-5(4)9-7/h1-3H,7H2,(H,8,9)

Upstream product

• 54231-32-2 3-chloro-2-nitropyridine 
• 2402-77-9 2,3-dichloro-pyridine 
• 79785-97-0 hydrazine hydrate 
• 6515-09-9 2,3,6-trichloropyridine 
• 462-08-8 pyridin-3-ylamine 

Downstream Products

• 40971-88-8 8-chlorotrazolo<1,5-a>pyridine 
• 500011-88-1 ethyl 1-(3-chloropyridin-2-yl)-3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylate 
• 210992-25-9 1-[1-(3-Chloro-pyridin-2-yl)-5-methyl-4-pyrazolyl]-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-propanone 
• 500011-88-1 2-(3-chloro-pyridin-2-yl)-5-oxo-pyrazolidine-3-carboxylic acid ethyl ester 
• 1247712-54-4 3-[(benzyloxy)methyl]-1-(3-chloropyridin-2-yl)-5-(trichloromethyl)-4,5-dihydro-1H-pyrazol-5-ol 
• 438450-39-6 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid 
• 1392234-78-4 C₂₃H₂₁Cl₂F₃N₆O₃ 
• 1392234-79-5 C₂₅H₂₃Cl₂F₃N₆O₃ 
• 1392234-80-8 C₂₂H₁₉Cl₂F₃N₆O₃ 
• 1392234-81-9 C₂₂H₁₇BrClF₃N₆O₃ 
• 1392234-82-0 C₂₁H₁₇Cl₂F₃N₆O₃ 
• 1392234-83-1 C₂₂H₁₈ClF₃N₆O₃ 
• 1392234-84-2 C₂₁H₁₅Cl₂F₃N₆O₃ 
• 1392234-85-3 C₂₂H₂₀ClF₃N₆O₃ 

Relevant articles and documents

Synthesis, antifungal and insecticidal activity of novel [1,2,4]triazolo[4,3-a]pyridine derivatives containing a sulfide substructure

A series of [1,2,4]triazolo[4,3-a]pyridine derivatives bearing a sulfide substructure was designed, synthesized and characterized via 1H·NMR, 13C·NMR, IR and elemental analyses. Bioassay Results indicated some of the derivatives displayed good fungicidal activity on Rhizoctonia cerealis, moderated insecticidal activity against Plutella xylostella and good insecticidal activity on Helicoverpa armigera. The inhibitory effects of compounds 4g and 4u against Rhizotonia cerealis were 70.9% at 50 μg mL-1; the IC50 values of compounds 4d and 4s against Plutella xylostella were 43.87 and 50.75 μg mL-1, respectively. And the IC50 values of compounds 4d, 4q, and 4s on Helicoverpa armigera were 58.3, 77.14 and 65.31 μg mL-1, respectively, which were better than that of commercial chlorpyrifos (103.77 μg mL-1).

Design, synthesis and insecticidal activities of novel anthranilic diamides containing polyfluoroalkyl pyrazole moiety

In order to discover new molecules with good insecticidal activities, a series of anthranilic diamides containing polyfluoroalkyl pyrazole were designed and synthesized, and their structures were characterized by 1H NMR and HRMS. Bioassays demonstrated that some of the title compound exhibited excellent insecticidal activities. The larvicidal activities of compound 8a, 8c, 8g, 8k and 8l against Mythimna separata Walker were 100% at 0.8?mg/L. The insecticidal activities of compound 8a, 8c, 8e, 8g, 8k and 8l against Plutella xylostella Linnaeus were 100% at 0.4?mg/L. Surprisingly compounds 8a and 8c still showed 100% larvicidal activities against Plutella xylostella Linnaeus at 0.08?mg/L comparable to the commercialized Chlorantraniliprole. The LC50 of compound 8a and 8c against M. separata is 0.048 and 0.043?mg/L respectively.

Synthesis and insecticidal activity of anthranilic diamides with hydrazone substructure

A series of anthranilic diamides with a hydrazone substructure was synthesised and characterised using 1H NMR, 13C NMR, IR and elemental analyses. The in vitro insecticidal activity of all the compounds was tested against Plutella xylostella. The results showed the synthesised compounds to possess good insecticidal activity. The LC50 values of compounds VIIg, VIIl, VIIm, VIIn exhibited excellent insecticidal activities, with the LC50 affording 7.92 mg L-1, 12.01 mg L-1, 0.62 mg L-1 and 10.71 mg L-1, respectively. These may prove to be useful as potential insecticidal agents.

Structure-based discovery and synthesis of potential transketolase inhibitors

Transketolase (TKL) plays a key role in plant photosynthesis and has been predicted to be a potent herbicide target. Homology modeling and molecular dynamics simulation were used to construct a target protein model. A target-based virtual screening was developed to discover novel potential transketolase inhibitors. Based on the receptor transketolase 1 and a target-based virtual screening combined with structural similarity, six new compounds were selected from the ZINC database. Among the structural leads, a new compound ZINC12007063 was identified as a novel inhibitor of weeds. Two novel series of carboxylic amide derivatives were synthesized, and their structures were rationally identified by NMR and HRMS. Biological evaluation of the herbicidal and antifungal activities indicated that the compounds 4u and 8h were the most potent herbicidal agents, and they also showed potent fungicidal activity with a relatively broad-spectrum. ZINC12007063 was identified as a lead compound of potential transketolase inhibitors, 4u and 8h which has the herbicidal and antifungal activities were synthesized based on ZINC12007063. This study lays a foundation for the discovery of new pesticides.

Microwave-assisted synthesis of novel 8-chloro-[1,2,4]triazolo[4,3-a]pyridine derivatives

A series of novel 1,2,4-triazolo[4,3- a]pyridine derivatives were synthesized from 2,3-dichloropyridine and hydrazine hydrate as starting materials by multistep reactions under microwave assistance, and their structures were characterized by 1H

Microwave-assistant synthesis, crystal structure and fungicidal activity of 3-Chloro-2-hydrazinylpyridine

A pyridine derivative i.e., 3-chloro-2-hydrazinylpyridine (C 5H6N3Cl) was synthesized under microwave irradiation and its structure was studied by X-ray diffraction and 1H NMR. The crystals are monoclinic, space group p21/c with a = 11.6276 (14), b = 3.8924 (5), c = 13.9558 (17) ?, α= 90.00, β= 103.447 (6), γ= 90.00°, V = 614.31(13)?3, Z = 4, F (000) = 296, Dc = 1.552g/cm3, μ= 0.52 cm-1, the final R = 0.0623 and wR = 0.1897. A total of 7008 reflections were collected, of which 1406 were independent (Rint = 0.0544). The fungicidal activity of this compound was also studied.

Synthesis and biological activity of novel sulfone derivatives containing a [1,2,4]triazolo[4,3-a]pyridine moiety

A series of novel sulfone derivatives containing a [1,2,4]triazolo[4,3-a]pyridine moiety was synthesized and characterized via 1H NMR, 13C NMR, IR, and elemental analyses. Bioassay results indicated some of the derivatives displayed good antifungal activities and insecticidal activity. The inhibition rates of 8-chloro-3-((2,6-difluorobenzyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine against Rhizotonia erealis and Helminthosporium maydis were 78.6% and 76.4% activities at 50?μg mL?1, respectively. And compound 8-chloro-3-(((6-chloropyridin-3-yl)methyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine showed >95% mortality at 500?μg mL?1 and >65% mortality at 200?μg mL?1 against Plutella xylostella, respectively. As well as 8-chloro-3-(((6-chloropyridin-3-yl)methyl)sulfonyl)-[1,2,4]triazolo[4,3-a]pyridine displayed >90% mortality at 500?μg mL?1 against Helicoverpa armigera. A preliminary structure activity relationship (SAR) is discussed.

Synthesis method of 3-chloro-2-hydrazinopyridine

The invention relates to a synthesis method of 3-chloro-2-hydrazinopyridine. The method comprises the following steps: carrying out sulfonation reaction on 3-chloropyridine serving as a raw material, and reacting the obtained intermediate with hydrazine hydrate to obtain the 3-chloro-2-hydrazinopyridine. The route is simple, the average yield of the product is not lower than 80%, and the purity of the product is 99.50% or above; reaction conditions are mild, operation is safe and simple, equipment requirements are not high, and the method is suitable for industrial production; and raw materials and auxiliary materials are conventional compounds, used solvents can be recycled, the catalyst is single, industrial three wastes are few, and the method is environment-friendly.

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.

Preparation method of chlorantraniliprole

The invention relates to the field of insecticide synthesis, and discloses a preparation method of chlorantraniliprole. The preparation method comprises the following steps: synthesis of an intermediate I, synthesis of an intermediate II and synthesis of chlorantraniliprole. The method comprises the following steps: reacting 2, 3, 6-trichloropyridine serving as a raw material with hydrazine hydrate under the action of a catalyst A to obtain 3, 6-dichloro-2-hydrazinopyridine, carrying out hydrogenation reduction reaction under the action of a catalyst B to obtain an intermediate I, reacting theintermediate I with diethyl maleate, and preparing the 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate under the action of a catalyst C, and hydrolyzing after bromination to obtain an intermediate II, and preparing chlorantraniliprole from the intermediate II. According to the invention, 2, 3, 6-trichloropyridine is adopted to replace 2, 3-dichloropyridine as a raw material to preparethe intermediate I, so that the defects of difficulty in obtaining the 2, 3-dichloropyridine raw material, harsh synthesis conditions, low yield and the like are avoided, the total reaction yield ofthe intermediate I is improved, the intermediate II is prepared by a one-pot method, the post-treatment operation is reduced, and the synthesis cost of chlorantraniliprole is reduced.