4214-74-8

Basic information

• Product Name: 2-Amino-3,5-dichloropyridine
• Synonyms: 3,5-dichloro-3-pyridylamine;3,5-Dichloro-2-AminoPyridine;2-AMINO-3,5-DICHLIROPYRIDINE;2-AMINO-3,5-DICHLOROPYRIDINE 99%;2-Pyridinamine, 3,5-dichloro-;2-Amino-3,5-dichloropyridine,97%;2-Amino-3,5-dichloropyridine,98%;(3,5-dichloro-2-pyridyl)amine
• CAS NO: 4214-74-8
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163
• EINECS: 224-143-5
• Product Categories: Amines;Pyridines;Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Amino-pyridine series
• Mol File: 4214-74-8.mol

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 268.76°C (rough estimate)
• Flash Point: 96 °C
• Appearance: Off-white to pink to beige/Powder or Crystals
• Density: 1.5462 (rough estimate)
• Vapor Pressure: 0.0507mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.43±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 119376
• CAS DataBase Reference: 2-Amino-3,5-dichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3,5-dichloropyridine(4214-74-8)
• EPA Substance Registry System: 2-Amino-3,5-dichloropyridine(4214-74-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39-28A-45-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4214-74-8(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT BEIGE TO GREY CRYSTALLINE POWDER OR FLAKES

Uses

3,5-Dichloropyridin-2-amine can be used as herbicidal active substances.

InChI:InChI=1/C5H4Cl2N2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9)/p+1

Upstream product

• 504-29-0 2-aminopyridine 
• 1072-98-6 5-chloro-2-pyridylamine 
• 16063-70-0 2,3,5-trichloropyridine 
• 133520-09-9 N-tert-Butyl-N'-(3,5-dichloro-pyridin-2-yl)-diazene N'-oxide 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 7782-50-5 chlorine 
• 5468-71-3 3,5-dichloropicolinamide 
• 7726-95-6 bromine 
• 110-86-1 pyridine 
• 39620-04-7 2-amino-3-chloropyridine 
• 171774-37-1 N-(3,5-dichloropyridin-2-yl)pyridinium aminide 

Downstream Products

• 73447-01-5 2-[(3,5-dichloro-pyridin-2-ylimino)-methyl]-phenol 
• 5437-33-2 3,5-Dichloro-2-pyridinol 
• 116608-20-9 6-chloro-2-phenyl-thiazolo[4,5-b]pyridine 
• 116608-17-4 N-(3,5-Dichloro-pyridin-2-yl)-thiobenzamide 
• 95729-13-8 N-(3,5-Dichloro-pyridin-2-yl)-4-fluoro-3-methyl-benzamide 
• 124522-22-1 2-p-tolyl-6-chlorothiazolo<4,5-b>pyridine 
• 95729-16-1 2-(4-Fluoro-2-methoxy-benzoylamino)-3,5-dichloropyridine 
• 80269-83-6 2-(4-fluorobenzoil)ammino-3,5-dicloropiridina 
• 76175-72-9 Benzyl-(3,5-dichloro-pyridin-2-yl)-amine 
• 76175-74-1 2-(o-clorobenzilammino)-3,5-dicloropiridina 

Relevant articles and documents

One-pot chemoselective bis(suzuki-miyaura cross-coupling): Efficient access to 3,9-Bis[(hetero)aryl]-4H-pyrido[1,2-a]pyrimidin-4-one derivatives under microwave irradiation

A one-pot chemoselective bis(Suzuki-Miyaura cross-coupling) reaction under microwave irradiation is reported for the 4H-pyrido[1,2-a]pyrimidin-4-one series. First, we ascertained an initial coupling reaction that was selectively carried out at the C-3 position of (7,9-dichloro-3-iodo-4-oxo-4H-pyrido[1,2-a] pyrimidin-2-yl)methyl acetate (4). Next, we developed an extremely efficient one-pot chemoselective bis(Suzuki-Miyaura cross-coupling) reaction, allowing us to substitute successively at the 3-and then at the 9-position of compound 4 with various boronic acids.

Selectfluor-promoted regioselective chlorination/bromination of 2-aminopyridines and 2-aminodiazines using LiCl/LiBr

Using LiCl as a chlorine source, the chlorination of 2-aminopyridines or 2-aminodiazines in the presence of Selectfluor and DMF is established under mild conditions. This method gives chlorinated pyridines or diazines in good to high yields with high regioselectivities. Also, this method is extended to the bromination of 2-aminopyridines or 2-aminodiazines by using LiBr. The regioselectivity of the chlorination reaction is strongly dependent upon the substituent pattern in either the 2-aminopyridines or 2-aminodiazines. The synthesis of Buparlisib from chlorinated pyridines was explored. A study of the mechanism revealed that this chlorination occurs via either a pyridine or diazine radical process.

A 2-amino -3,5-dichloro pyridine synthesis method

The invention belongs to the field of organic synthesis and in particular relates to a synthetic method of 2-amino-3,5-dichloropyridine. The synthetic method comprises the following steps: reacting raw materials including 2-amino-5-chloropyridine and N-chlorosuccinimide for 0.5-24 hours in a molar weight of 1: (0.5-5) in a proper solvent at 0-100 DEG C to generate a 2-amino-3,5-dichloropyridine crude product and purifying to obtain the pure product 2-amino-3,5-dichloropyridine. The synthetic method has the beneficial effects that the reaction raw materials are available and are reasonable in prices; meanwhile, heavy metals and corrosive gases are not used in the preparation reaction; the reaction is mild; the synthetic method does not have special requirements for reaction equipment and common corrosion resistant equipment can be used for production; besides, with the advantageous conditions such as moderate reaction conditions, easily controlled reaction and high product purity, and the process is easy to popularize.

CFBSA: a novel and practical chlorinating reagent

A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.

Synthesis and study of nucleic acids interactions of novel monomethine cyanine dyes

Six asymmetric monomethine cyanine dyes have been synthesized and their spectral characteristics and interaction with double stranded (ds)DNA have been investigated for their prospective use as fluorescent markers in molecular biology. Therefore, the non-covalent binding of the compounds with dsDNA was explored. Apart from the fluorescence spectroscopy, the study includes UV/Vis spectrophotometry and circular dichroism spectroscopy, as well as the thermal melting experiments. Although the compounds show relatively low binding affinity toward dsDNA and do not have intrinsic fluorescence, in the presence of dsDNA they exhibited considerable enhancement in fluorescence intensity. Therefore the studied dyes show interesting platform for future modifications directed toward more sequence selective derivatives. The compound with the highest affinity toward dsDNA showed interesting anti-proliferative potential and specificity.

Halogenation of pyridinium-N-(2'-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

The regioselective halogenation of pyridinium-N-(2'-pyridyl)aminide 1 with N-chloro, bromo or iodosuccinimide under mild conditions is described. The method, combined with a reduction of the N-N bond, allows an easy preparation of 5-halo and 3,5-dihalo-2-aminopyridines 4.

Process for the production of 2-amino-3-hydroxypyridine derivatives

2-Amino-3-hydroxy-5-chloropyridine and 2-amino-3-hydroxy-5-bromopyridine are produced by selective hydrolysis of corresponding 2-amino-3,5-dihalopyridines.