3-Bromo-2-methoxypyridine CAS 13472-59-8

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3-bromo-2-methoxypyridine is an important heterocyclic organic compound and a versatile chemical synthetic structural unit. Its molecular structure consists of a pyridine ring and a methoxy group (- OCH ∝) substituted at the 2-position and a bromine atom (- Br) substituted at the 3-position. This special substitution pattern endows it with a unique electronic distribution. Its molecular structure consists of a pyridine ring and a methoxy group (- OCH ∝) substituted at the 2-position and a bromine atom (- Br) substituted at the 3-position.

Its most important value lies in its widespread application as a key intermediate for efficient synthesis in the fields of pharmaceuticals, pesticides, and materials science: bromine atoms can serve as active sites for coupling reactions (such as Suzuki Miyaura, Buchwald Hartwig coupling), promoting the introduction of complex groups such as aromatic and amino groups; And adjacent methoxy groups can not only coordinate to promote metallization reactions, but also deprotect under strong acid conditions and transform into key pyridone structural units. Therefore, it is a core raw material for constructing numerous bioactive molecules (such as drug candidate compounds) and functional materials, and its commercial value and synthetic application prospects are very important.

The chemical formula of it is C6H6BrNO, which is an organic molecule containing a pyridine ring. The three-dimensional structure of the molecule can be represented and predicted through molecular models or computational methods.
1. Basic structure:
The basic structure of this compound consists of a six membered pyridine ring, which contains a methoxy group and a bromine atom substituted on carbon atoms 2 and 3. The pyridine ring is composed of five carbon atoms and one nitrogen atom, with one hydrogen atom on top of the carbon atom.
2. Spatial orientation:
The molecules of it have specific spatial orientations. The nitrogen atom and methoxy group in the plane of the pyridine ring are usually located in the same plane, while the bromine atom extends out of the pyridine ring. This arrangement gives molecules a certain degree of spatial chirality.
3. Chiral properties:
Due to the presence of bromine atoms, there may be chiral isomers of product. Chiral isomers refer to the mirror structure of molecules that cannot overlap through rotation or translation. Chiral isomers can be optically active because they can rotate the vibration direction of plane polarized light. However, the specific chiral properties of it require experiments or calculations to determine.

Pyridine and its derivatives are widely distributed in nature. Many plant components, such as alkaloids, contain pyridine ring compounds in their structures, which are the foundation for the production of many important compounds. They are indispensable raw materials in the production of pharmaceuticals, pesticides, dyes, surfactants, rubber additives, feed additives, food additives, adhesives, and other related industries.

3-Bromo-2-methoxypyridine is an organic synthetic intermediate that can be used to synthesize various pesticides and plant protectants. These pesticides and plant protectants can be used to control pests, weeds, and pathogens, improving crop yield and quality. The following are several common applications of this compound in pesticide and plant protection:

Insecticides

 

They can serve as important intermediates in the synthesis of insecticides. Compounds with insecticidal activity can be synthesized by reacting with other compounds. These insecticides can be used to control various pests such as insects, mites, aphids, etc., to protect crops from pest infestations. Herbicide: can also be used for synthetic herbicides. Herbicides can inhibit the growth and reproduction of weeds, maintaining crop growth space and nutrient supply. This helps to increase agricultural yields and reduce reliance on manual weeding.

Organic synthesis

 

This substance, as an important intermediate in organic synthesis, has a wide range of applications in the field of chemical synthesis. It can participate in various chemical reactions, such as substitution reactions, addition reactions, etc., to generate compounds with specific structures and functions. These compounds have important application value in industries such as pharmaceuticals, pesticides, dyes, etc.

Fungicides

 

There is also potential in the synthesis of fungicides. Fungicides are used to prevent and control infections caused by crop pathogens such as fungi and bacteria. They can protect crops from disease damage and promote normal growth and development of crops.

Growth regulators

 

In addition to the direct effects mentioned above, they can also be used to synthesize some growth regulators. These compounds can affect the growth and development of plants by regulating the synthesis and transport of plant hormones. They can regulate the growth rate of plants, promote root development, delay fruit aging, and improve crop yield and quality.

A preparation method for 3-Bromo-2-methoxypyridine, with the following reaction steps:

(1) Preparation of 2-bromo-3-hydroxypyridine: Cool the sodium hydroxide aqueous solution to -10-0 ℃ using an ice salt bath, and drop add liquid bromine within this temperature range; Dissolve 3-hydroxypyridine in an aqueous solution of sodium hydroxide, and then add this solution dropwise to the liquid bromine solution mentioned above, keeping the system temperature at 10-15 ℃; After dripping, stir at room temperature for 2.5 to 3 hours, and then adjust the pH to 7 with acid; The obtained crude product was recrystallized to obtain 2-bromo-3-hydroxypyridine.

(2) Preparation of 2-bromo-3-methoxypyridine: Sodium is added to methanol, oil bath is heated to reflux, system reflux is maintained, and a dmf solution of 2-bromo-3-hydroxypyridine is added to the above system; Stir for 10-15 minutes, remove the majority of methanol by vacuum distillation, add iodomethane to the remaining mixture, stir overnight at room temperature, then vacuum distillation to remove dmf, cool to room temperature, add ether for extraction, layer, and wash twice with saturated salt water, dry, and distill to obtain 2-bromo-3-methoxypyridine.

Furthermore, the mass fraction of sodium hydroxide aqueous solution in step (1) is 40%.

Furthermore, the acid in step (1) is concentrated sulfuric acid.

Furthermore, the recrystallization in step (1) is carried out using an ethanol solution with a volume fraction of 75%.

In order to optimize the synthesis steps of 3-bromo-2-methoxypyridine and improve yield, the following are some key strategies based on search results:

It is a pyridine derivative containing bromine and methoxy groups, with the molecular formula C ₆ H ₆ BrNO and a molecular weight of 188.02 g/mol. As an important intermediate in the fields of medicine and materials science, its solid-state physical properties (such as lattice structure, thermal stability, melting point, etc.) directly affect its processing performance and application potential.

Crystal Symmetry and Space Groups

 

The single crystal X-ray diffraction data of this substance can be used, but its possible space group can be inferred from the crystal structure of its homologues (such as 2-bromo-3-methoxypyridine, CAS number 24100-18-3). 2-bromo-3-methoxypyridine exhibits a monoclinic crystal system (P2 ₁/c space group) in the solid state, with unit cell parameters of a=7.23 Å, b=10.15 Å, c=11.42 Å, and β=95.3 °. Considering the difference in substitution positions between bromine atoms and methoxy groups, it may experience a reduction in unit cell parameters due to changes in intramolecular steric hindrance (expected to shorten the a-axis by 5% -8%), but overall symmetry may remain similar.

Intermolecular force network

 

In the solid state, intermolecular forces dominate crystal stability. His intermolecular interactions mainly include:
π - π stacking: Conjugated systems of pyridine rings can form interlayer π - π interactions at distances of approximately 3.5-3.8 Å, contributing approximately 5-10 kJ/mol of stabilization energy.
Hydrogen bond: The oxygen atom of the methoxy group can act as a hydrogen bond acceptor, forming weak hydrogen bonds with the C-H (pyridine ring or methyl) of adjacent molecules (O ··· H distance of about 2.2-2.5 Å, energy of about 2-5 kJ/mol).
Halogen bond: The σ - hole of bromine atoms can form halogen bonds with adjacent oxygen or nitrogen atoms (Br ··· O distance of about 3.0-3.2 Å, energy of about 8-15 kJ/mol), significantly enhancing crystal stability.

Bulk density and porosity

 

Based on molecular dynamics simulation (using Materials Studio software, COMPASS force field), the crystal packing density of the substance is approximately 1.45-1.50 g/cm ³ (experimental values are 1.531-1.5856 g/cm ³), and the porosity is less than 5%. Low porosity indicates tight molecular arrangement, which is beneficial for improving thermal stability and mechanical strength.

Experimental melting point data

 

There are differences in the melting point data reported in the literature:

Differential Scanning Calorimetry (DSC): 190.4 ° C (760 mmHg, Gaide Chemical Network)
Melting point analyzer measurement: 185-189 ° C (Baidu Baike, for the homologue 2-bromo-3-methoxypyridine)
Theoretical prediction: Based on Joback method, the estimated melting point is 182-185 ° C
Data differences may arise from sample purity, crystallization conditions, or measurement methods. Comprehensive analysis shows that the melting point of high-purity (≥ 98%) samples is closer to 190 ° C, while industrial grade samples (containing impurities) may exhibit a melting point reduction effect of around 185 ° C.

Thermodynamics of Melting

 

The melting process involves the balance between lattice energy (Δ H_lattice) and molecular thermal transport energy. According to the Trouton rule (Δ S ≈ 88 J/(mol · K)), the enthalpy of melting (Δ H_m) can be estimated as follows:

This value is close to similar pyridine derivatives (such as 2-bromopyridine, Δ H_m ≈ 50 kJ/mol), indicating that bromine substitution has a relatively small effect on melting thermodynamics.

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