16110-09-1

Basic information

• Product Name: 2,5-Dichloropyridine
• Synonyms: 2,5-Dichloropyridine, 98% 5GR;2,5- twochlorine pyridine;2,5-Dichiloropyridine;2,5-Chloro pyridine;2,5-dichloro-pyridin;4-Aminophenylacetamide;2,5-DICHLORPYRIDINE;2,5-Dichloropyridine97%
• CAS NO: 16110-09-1
• Molecular Formula: C5H3Cl2N
• Molecular Weight: 147.99
• EINECS: 240-278-2
• Product Categories: Building Blocks;C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl chloride;Pyridine;pyridine derivative;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Chloropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Chlorinated heterocyclic series
• Mol File: 16110-09-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 59-62 °C(lit.)
• Boiling Point: 190-191 °C
• Flash Point: 112 °C
• Appearance: White to slightly yellow/Crystalline Solid
• Density: 1.5159 (rough estimate)
• Vapor Pressure: 0.904mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Room temperature.
• PKA: -2.25±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 108886
• CAS DataBase Reference: 2,5-Dichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dichloropyridine(16110-09-1)
• EPA Substance Registry System: 2,5-Dichloropyridine(16110-09-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36
• RIDADR: UN2811
• WGK Germany: 3
• RTECS: US8225000
• HazardClass: IRRITANT
• Hazardous Substances Data: 16110-09-1(Hazardous Substances Data)

Usage

Description

2,5-Dichloropyridine is a white to slightly yellow crystalline solid that is commonly utilized as a reagent in chemical synthesis due to its unique chemical properties. It is known for its ability to undergo cross-coupling reactions with arylboronic acids in the presence of a specific palladium-based catalyst.

Uses

Used in Pharmaceutical Synthesis:
2,5-Dichloropyridine is used as a key reagent for the synthesis of various pharmaceutical compounds. One notable application is in the production of 4-benzodiazepine-2,5 diones, which serve as Hdm2 antagonists and inhibitors of ERK protein kinase. These compounds have potential therapeutic applications in the treatment of certain diseases and conditions.
Used in Chemical Research:
In the field of chemical research, 2,5-Dichloropyridine is employed in the synthesis of 6-halo-pyridin-3-yl boronic acids and esters. These compounds are valuable intermediates in the development of new chemical entities and materials.
Used in Catalyst-Assisted Reactions:
2,5-Dichloropyridine is used as a reactant in cross-coupling reactions with arylboronic acids, facilitated by the catalyst [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride. This reaction is significant in the synthesis of various organic compounds and materials, contributing to the advancement of chemical research and development.

Synthesis Reference(s)

Synthetic Communications, 20, p. 2971, 1990 DOI: 10.1080/00397919008051514

InChI:InChI=1/C5H3Cl2N/c6-4-1-2-5(7)8-3-4/h1-3H

Upstream product

• 13473-01-3 5-chloro-2-methoxypyridine 
• 694-85-9 1-methyl-2-pyridone 
• 75-44-5 phosgene 
• 4214-78-2 5-chloro-1-methylpyridin-2(1H)-one 
• 108-88-3 toluene 
• 1851-22-5 3-chloropyridine-N-oxide 
• 4214-79-3 5-chloro-2-pyridinol 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 1072-98-6 5-chloro-2-pyridylamine 
• 7647-01-0 hydrogenchloride 
• 107-06-2 1,2-dichloro-ethane 
• 624-28-2 2,5-dibromopyridine 
• 10469-09-7 3,4,5,6-tetrachloropyridinecarboxylic acid 

Downstream Products

• 4214-79-3 5-chloro-2-pyridinol 
• 40771-41-3 2-mercapto-5-chloro-pyridine 
• 87394-65-8 1-(5-chloropyridin-2-yl)piperazine 
• 4214-78-2 5-chloro-1-methylpyridin-2(1H)-one 
• 160426-48-2 5-Chloro-2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine 
• 13473-01-3 5-chloro-2-methoxypyridine 
• 553-26-4 4,4'-bipyridine 
• 77917-54-5 1-Benzyl-4-[4-(5-chloro-pyridin-2-ylamino)-benzyl]-piperazine-2,3-dione 
• 92992-92-2 N₁-(5-chloropyridin-2-yl)ethane-1,2-diamine 
• 58254-76-5 5-chloro-2-phenylpyridine 
• 131237-73-5 5-chloro-α-(4-chlorophenyl)-2-pyridineacetonitrile 
• 129708-80-1 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine 
• 87423-83-4 2-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)pyridine 
• 5552-44-3 ethyl 2,5-pyridinedicarboxylate 

Relevant articles and documents

Continuous production process of 2, 3, 5-trichloropyridine

According to a continuous production process of 2, 3, 5-trichloropyridine, a continuous tubular chlorinator is adopted, pyridine is taken as a starting raw material, chlorination reaction is continuously carried out step by step by virtue of a catalyst 1 and a catalyst 2 which are independently researched and developed, and 2, 5-dichloropyridine and 2, 3, 5-trichloropyridine are prepared in sequence. In the preparation process of a catalyst 1 and a catalyst 2, the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to nickel tetracarbonyl is 1.2: 1: 3.7: 2.5, and the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to sodium hexachlororhodate hydrate is 1.2: 1: 3.7: 15. By means of the continuous tubular chlorinator, cheap and easily available pyridine is used as a starting raw material, chlorine atoms are introduced step by step through catalytic chlorination, the atom economy is good, the reaction selectivity is good, the yield of 2, 3, 5-trichloropyridine can be stabilized at 80% or above, the production efficiency is high, the process is easy to control, and the method is environmentally friendly and suitable for industrial production.

Method for preparing 3,6-dichloro-pyridine-2-carboxylic acid through hydrogenation reduction of 3,4,5,6-tetrachloropyridine-2-carboxylic acid

The invention discloses a method for preparing 3,6-dichloro-pyridine-2-carboxylic acid through hydrogenation reduction of 3,4,5,6-tetrachloropyridine-2-carboxylic acid and belongs to the technical field of production of chemical products. Under specific conditions of temperature, pressure, PH value and the like, chlorine on a pyridine ring is removed through catalytic hydrogenation and the 3,6-dichloro-pyridine-2-carboxylic acid is prepared. According to the method, a clean and environment-friendly catalytic hydrogenation process is used, the 3,4,5,6-tetrachloropyridine-2-carboxylic acid is subjected to hydrogenation reduction high-selectively to prepare the 3,6-dichloro-pyridine-2-carboxylic acid, highly toxic dangerous goods such as reducing agent hydrazine and dichloromethane are not used in the production process, the reaction conditions are mild, the device is simple and easy and convenient to operate, the cost is low, production zero release of the 3,6-dichloro-pyridine-2-carboxylic acid is realized, popularization and application of the green chemical technology are accelerated, and the method has remarkable economic advantages and environment-friendly advantages.

Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding chlorides

An efficient method for the synthesis of aryl and heteroaryl chlorides is described. The reactions of aryl and heteroaryl bromides with tetramethylammonium chloride proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding chlorides in satisfactory to excellent yields.