5-bromopyridine-3-carboxylate

5-Bromopyridine-3-carboxylic acid esters are a class of organic compounds. In its molecular structure, the 5th position of the pyridine ring is replaced by a bromine atom, and the 3rd position is connected with a carboxylic acid ester group. This structure gives it unique chemical properties.
In terms of reactivity, bromine atoms have high reactivity and can participate in many nucleophilic substitution reactions. The capped bromine atom is a good leaving group. When attacked by nucleophiles, it is easy to leave and introduce new groups at the 5th position on the pyridine ring. For example, under alkaline conditions with alcohols, bromine can be replaced by alkoxy groups to form corresponding ether derivatives.
Its carboxylic acid ester group also has important chemical properties. The ester group can undergo hydrolysis under acidic or alkaline conditions. In acidic media, hydrolysis generates 5-bromopyridine-3-carboxylic acid and corresponding alcohols; under alkaline conditions, hydrolysis is more thorough, generating carboxylic salts and alcohols, and this process is more rapid than acidic hydrolysis.
Furthermore, the nitrogen atom of the pyridine ring has a certain alkalinity and can form salts with acids, thus affecting the solubility and reactivity of the compound in different solvents. At the same time, the electron cloud distribution of the pyridine ring allows 5-bromopyridine-3-carboxylate to participate in some reactions involving electron transfer of the pyridine ring, such as electrophilic substitution reactions, but the reaction check point is related to the electronic effect of the substituents attached to the pyridine ring. Overall, 5-bromopyridine-3-carboxylate has rich chemical properties and is widely used in the field of organic synthesis.

The common synthesis methods of 5-bromopyridine-3-carboxylate are as follows:
First, pyridine is used as the starting material. The pyridine is first brominated. By selecting a suitable bromination reagent, such as liquid bromine, in the presence of a suitable catalyst (such as iron or iron salt), bromine atoms can be introduced into the pyridine ring to generate 5-bromopyridine. Subsequently, 5-bromopyridine is carboxylated, for example, by the Grignard reagent method, 5-bromopyridine is reacted with magnesium to make Grignard reagent, and then reacted with carbon dioxide to introduce carboxyl groups, and finally esterified with the corresponding alcohol under acid catalysis to obtain 5-bromopyridine-3-carboxylic acid ester.
Second, start from 3-pyridine carboxylic acid. 3-pyridine carboxylic acid is first esterified with alcohol under acid catalysis to obtain pyridine-3-carboxylic acid ester. After that, the pyridine ring is brominated, using a suitable brominating agent and reaction conditions, such as N-bromosuccinimide (NBS) in the presence of an initiator, to achieve the bromination of the pyridine ring at the 5th position, thereby obtaining the target product 5-bromopyridine-3-carboxylate.
Third, the coupling reaction catalyzed by palladium. A suitable halopyridine derivative (containing a bromine atom in a suitable position) and a borate ester or boric acid derivative containing a carboxyl ester structure are selected. Suzuki coupling reaction occurs in a palladium catalyst (such as tetra (triphenylphosphine) palladium, etc.), a base and a suitable solvent system, and 5-bromopyridine-3-carboxylate can also be synthesized through this reaction path. In the specific synthesis process, the appropriate synthesis method should be reasonably selected according to the availability of raw materials, the ease of operation of the reaction conditions and the purity requirements of the target product.

5-Bromopyridine-3-carboxylic acid esters have extraordinary uses in the fields of medicine, pesticides and materials.
In the field of medicine, it is often a key intermediate. Due to the unique structure of the pyridine ring and bromine atoms, compounds with specific pharmacological activities can be synthesized by chemical modification. For example, when developing antibacterial drugs, they can be modified according to their structure, so that the synthetic drugs can accurately act on specific bacterial targets and interfere with the bacterial metabolism process to achieve antibacterial effect. And its structure helps to improve the fat solubility of the drug, improve the absorption, distribution, metabolism and excretion characteristics of the drug in the body, and improve the efficacy of the drug.
In the field of pesticides, 5-bromopyridine-3-carboxylate is also indispensable. After rational design and reaction, it can be converted into high-efficiency pesticide ingredients. For example, according to the special physiological mechanism of some pests, the designed and synthesized pesticides can specifically act on the nervous system or digestive system of pests, inhibit the activity of related enzymes, and cause the physiological function of pests to be disordered and die. At the same time, its structure can optimize the environmental compatibility of pesticides, reduce the impact on non-target organisms, and reduce environmental pollution.
In the field of materials, 5-bromopyridine-3-carboxylate can participate in the synthesis of polymer materials. By copolymerizing with other monomers, the material is endowed with unique properties. When preparing photoelectric materials, the introduction of this structure can change the electron cloud distribution of the material, affect its optical and electrical properties, and make the material exhibit good photoelectric conversion performance in Light Emitting Diode, solar cells and other devices. And it can improve the stability and corrosion resistance of the material, expand the application range of the material, and play an important role in aerospace, electronic equipment protection, etc.

5-Bromopyridine-3-carboxylic acid ester, which is a key intermediate in the field of organic synthesis, is widely used in many fields such as medicine, pesticides and material science. Its market price often fluctuates significantly due to quality, purity, supply source and market supply and demand conditions.
In the past, if you look for its price in an ancient book about process technology like "Tiangong Kaiwu", it may be difficult to find it, because it was not available in the book era. However, if you are in the current market and want to know its price, you can start with the following numbers.
First, purity is the key factor. High purity, such as for high-end pharmaceutical research and development, requires extremely low impurity content, its preparation process is complicated, the cost is high, and the price may reach hundreds of yuan per gram. And slightly lower purity, suitable for ordinary industrial synthesis, the price is relatively close to the people, or tens of yuan per gram.
Second, the source of supply also has an impact. Domestic large-scale, mature and scale-effective manufacturers, due to effective cost control, produce 5-bromopyridine-3-carboxylate prices or more competitive. On the other hand, those who rely on imports, or due to transportation, tariffs and other costs, prices rise.
Third, the market supply and demand situation plays a significant role. When the pharmaceutical industry's demand for specific drugs containing this intermediate surges, causing the market to be in short supply, prices will rise; on the contrary, if there are many manufacturers and excess supply, prices will be under downward pressure.
For example, in chemical raw material trading platforms, products of different specifications are common, and the price difference is obvious. Purchasers need to consider quality and cost comprehensively according to their actual needs to obtain a suitable price.

The safety and toxicity of 5-bromopyridine-3-carboxylate are really important questions. This compound is used in many fields such as chemical industry and pharmaceutical research and development, so it is crucial to clarify its safety and toxicity characteristics.
When it comes to safety, 5-bromopyridine-3-carboxylate is stable under conventional environments if it is properly stored away from open flames and hot topics. However, most of it is a chemical synthesis product, and some operations need to be done with caution. If it is prepared in a laboratory or industry, it must be well ventilated, because it may evaporate trace harmful gases and irritate the respiratory tract. Operators should also wear appropriate protective equipment, such as protective glasses, gloves and masks, to prevent direct contact with the skin and eyes, causing discomfort.
As for toxicity, although there is no detailed and unified conclusion, it may have certain toxicity based on the study of its structure and similar compounds. Animal experiments or show that high doses of exposure may cause damage to the liver, kidneys and other organs. If ingested inadvertently, it may cause gastrointestinal discomfort, such as nausea, vomiting, abdominal pain and other symptoms. After skin contact, it may cause allergic reactions, such as redness, swelling, itching. And long-term inhalation of its dust or volatiles, or potential carcinogenic risk.
In summary, when handling 5-bromopyridine-3-carboxylate, strict safety procedures must be followed to minimize risk and ensure personal and environmental safety.