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Methyl 2-bromovalerate is a colorless to pale yellow liquid with a pungent odor. The bromine atom in its molecular structure, together with the ester group, is located on the carbon chain of pentanoic acid, giving this compound significant reactivity. As an important organic synthetic intermediate, it can act as an electrophilic reagent to participate in substitution reactions through the bromine atom, forming carbon-carbon or carbon-heteroatom bonds.It can also undergo condensation reactions by utilizing the acidity of the α-hydrogen, playing a crucial role in drug synthesis, materials science, and fine chemical industries.
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Chemical Formula |
7H13BrO2 |
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Exact Mass |
208.01 |
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Molecular Weight |
209.08 |
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m/z |
208.01 (100.0%), 210.01 (97.3%), 209.01 (7.6%), 211.01 (7.4%) |
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Elemental Analysis |
C, 40.21; H, 6.27; Br, 38.22; O, 15.30 |
Synthesis via bromination of methyl valerate
► Starting material:
Methyl valerate (CAS No. 624-24-8)
Bromine (Br₂) or other bromination reagent
► Reaction conditions:
Usually needs to be carried out in the presence of a catalyst, e.g., p-toluenesulfonic acid.
The reaction temperature needs to be precisely controlled to ensure selectivity and yield.
The reaction time is determined by the progress of the reaction and is usually monitored by thin layer chromatography (TLC) or gas chromatography (GC).
► Synthesis Procedure:
Add methyl valerate and an appropriate amount of catalyst to the reaction vessel.
Bromine or other bromination reagent is added slowly and dropwise while maintaining the reaction temperature in the appropriate range.
Upon completion of the reaction, post-treatments such as extraction, washing, drying and distillation are carried out to obtain purified α-bromopentanoate.
► Reaction mechanism:
Bromine undergoes bromination with methyl valerate in the presence of a catalyst to produce methyl 2-bromovalerate.
Synthesis by bromination of isovaleric acid and subsequent esterification
► Starting material:
Isovaleric acid (CAS No. 503-74-2)
Bromine (Br₂) or other bromination reagent
Methanol (as esterification reagent)
► Reaction conditions:
Bromination reactions usually need to be carried out in the presence of a catalyst such as red phosphorus.
Esterification reactions require acidic or basic conditions, such as concentrated sulfuric acid as a catalyst.
Reaction temperature and time should be determined according to the specific reaction process.
► Synthesis steps:
Bromination: isovaleric acid and appropriate amount of catalyst are added to the reaction vessel, and bromine is added slowly and dropwise to produce 2-bromoisovaleric acid.
Esterification reaction: 2-bromo isovaleric acid is esterified with methanol under acidic or alkaline conditions to produce α-bromopentanoate.
After the completion of the reaction, post-treatments such as extraction, washing, drying and distillation are carried out to obtain the purified product.
Role of α-bromopentanoate in organic synthesis reaction
Role of α-bromopentanoate in organic synthesis reaction
α-bromopentanoate is mainly used as bromine reagent and key intermediate in organic synthesis reaction, through the introduction of bromine atoms or the construction of a specific carbon skeleton, to participate in a variety of organic conversion reactions, the specific roles are as follows:
Participate in the bromination reaction as a bromine reagent
The bromine atoms in α-bromopentanoate have a higher reactivity, and can be used to brominate with many kinds of organic compounds under the action of the catalyst.
The bromine atom in α-bromopentanoate has high reactivity and can react with a variety of organic compounds under the action of catalyst. For example:
1) Bromination of olefin: under specific conditions, α-bromopentanoate can react with olefin by addition, introducing bromine atom into olefin molecule to produce bromo alkane. This type of reaction is often used in drug synthesis to construct molecular structures with specific biological activities.
2) Bromination of aromatic hydrocarbons: Through classical bromination methods such as the Fourier-Gram reaction, methyl 2-bromopentanoate introduces bromine atoms into the benzene ring of aromatic hydrocarbons to produce bromoaromatic hydrocarbons. These compounds have important application value in material science and drug development.
The role of α-bromopentanoate in the construction of complex molecules
The role of methyl 2-bromovalerate in the construction of complex molecules is mainly reflected in the synthesis of polycyclic compounds and chiral molecules as a key intermediate, which can realize the precise construction of the molecular skeleton and functional modification through the reactivity of bromine atoms and ester groups. The following is the specific analysis:
Synthesis of polycyclic compounds: bromine-driven coupling reactions
As a highly efficient leaving group, the bromine atom (Br) of α-bromopentanoate can be involved in a variety of coupling reactions, and has become a core tool for the construction of complex polycyclic structures. For example:
► Suzuki coupling reaction: in the presence of a palladium catalyst, α-bromopentanoate reacts with arylboronic acids to efficiently generate biphenyl analogs. Such compounds can be used in materials science to design high-performance polymers or as molecular backbones with specific biological activities in drug discovery.
Heck reaction: Through coupling with olefins, methyl 2-bromopentanoate can introduce unsaturated bonds and provide key sites for subsequent cyclization reactions to build complex molecules containing cyclic olefin structures.
Case: A research team successfully synthesized a biphenyl analog with anti-breast cancer activity using the Suzuki coupling reaction of α-bromopentanoate with arylboronic acid.
► Chiral molecule synthesis: synergistic effect of bromine atom and ester group
In the molecular structure of α-bromopentanoate, the bromine atom and ester group (CO₂Me) can be synergistically involved in the reaction, which provides a dual reactive site for the synthesis of chiral molecules:
► Chiral source strategy: Using α-bromopentanoate as a source of chirality, molecules with specific chiral properties can be directly obtained by chemical modification (e.g., hydrolysis of ester group, substitution of bromine atom). For example, it is converted into chiral alcohols or chiral amines for the construction of chiral drugs or catalysts.
Chiral auxiliary group strategy: In asymmetric synthesis, the ester group of α-bromopentanoate can be used as a chiral auxiliary group to induce the formation of a chiral center of the product via a stereoselective reaction (e.g., Diels-Alder reaction). Upon completion of the reaction, the ester group can be easily removed by steps such as hydrolysis or reduction to obtain the target chiral molecule.
Case in point: In the synthesis of chiral anti-inflammatory drugs, the ester group of methyl 2-bromopentanoate was used as a chiral auxiliary group to induce the stereoselectivity of the cycloaddition product via the Diels-Alder reaction. The final product showed twice the inhibitory activity against COX-2 enzyme than conventional non-chiral drugs with significantly lower side effects.
► Molecular Backbone Modification: Precise Introduction and Transformation of Bromine Atoms
The bromine atom of α-bromopentanoate can be replaced by other functional groups through nucleophilic substitution, elimination and other reactions, thus realizing precise modification of the molecular backbone:
Functional group transformation: the bromine atom can be replaced by amino (NH₂), hydroxyl (OH), alkoxy (OR), etc. to introduce new reaction sites or bioactive groups. For example, α-bromopentanoate can be converted into a molecule with neuroprosthetic activity through amino substitution of the bromine atom.
Molecular skeleton modification: precise introduction and conversion of bromine atoms
The bromine atom of alpha bromopentanediol acid can be replaced by other functional groups through nucleophilic substitution, elimination, and other reactions, thereby achieving precise modification of the molecular skeleton:
Functional group conversion: Bromine atoms can be replaced by amino (NH ₂), hydroxyl (OH), alkoxy (OR), etc. to introduce new reaction sites or biologically active groups.
For example, alpha bromopentanediol esters can be converted into molecules with neural prosthesis activity through amino substitution of bromine atoms. Chain extension or shortening: Through the elimination reaction of bromine atoms (such as E2 elimination), olefins or alkenes can be produced, thereby extending or shortening the molecular carbon chain. This strategy has important applications in the synthesis of natural product analogues or drug metabolites.
For example, in the synthesis of nerve growth factor (NGF) analogs, the bromine atom of alpha bromovalerate is replaced by an amino group to generate molecules with TrkA receptor affinity. This molecule significantly promotes neuronal survival and axonal extension in animal models, providing a new strategy for the treatment of spinal cord injury.
Key intermediates of anti chronic pain drugs
In the field of analgesics, 2-bromovalerate methyl ester is a core intermediate of the new generation of non opioid chronic neuropathic pain treatment drugs. This new type of analgesic drug does not act on opioid receptors at all, so it does not produce the addictive side effects of traditional opioid analgesics. The 2-valeric acid structural fragment in its molecule is introduced by nucleophilic substitution reaction of 2-bromopentanoic acid methyl ester, which can significantly enhance the selectivity of the drug towards the target.
As a "tool molecule" in the field of pharmaceutical synthesis and organic chemistry, α-bromopentanoate has unique chemical properties and a wide range of application values that cannot be ignored. From anti-tumor drugs to nerve repair agents, from traditional synthesis to green technology, its industrial chain is being extended and improved. In the future, with technological innovation and market demand growth, α-bromopentanoate is expected to show its potential in more fields, contributing to human health and sustainable development.
Methyl 2-bromovalerate (also known as α-bromopentanoate) is a class of structurally typical and highly reactive α - bromocarboxylic acid ester compounds. In its molecular structure, the alpha carbon atom simultaneously connects the bromine atom and the methyl ester group, forming a strong electrophilic reaction center. It combines the substitution reaction activity of brominated compounds with the stability and derivatization potential of ester groups, making it an indispensable fine chemical intermediate in the fields of organic synthesis, medicine, pesticides, and materials.
Key uses in the field of pesticides and agricultural chemicals
α-bromopentanoate is an important intermediate in pesticide synthesis, used in the preparation of herbicides, fungicides, insecticides, and plant growth regulators. Its α-bromoester structure can endow pesticide molecules with high biological activity, systemic absorption, and environmental compatibility.
Alpha bromoesters are key synthetic units of herbicides such as acetyl lactate synthase (ALS) inhibitors and protoporphyrinogen oxidase (PPO) inhibitors
ALS inhibitor herbicides: 2-bromopentanoic acid methyl ester undergoes nucleophilic substitution reaction with heterocyclic amines (such as pyrimidine amine and triazine amine) to generate sulfonylurea and imidazolinone herbicide intermediates.
This type of herbicide effectively controls grass and broad-leaved weeds by inhibiting the synthesis of branched chain amino acids in plants.
It has the characteristics of low toxicity, high efficiency, and high selectivity. The propyl side chain can optimize weed control activity and crop safety.
PPO inhibitor herbicides: intermediates of diphenyl ether and cyclic imide herbicides are generated through cyclization and oxidation reactions. They exert their effects by inhibiting plant chlorophyll synthesis and are used for weed control in corn, soybean, and cotton fields.
Fungicide: Methyl 2-bromopentanoate is used as an intermediate for the synthesis of triazole, morpholine, and thiazole fungicides. By modifying the molecular structure, the fungicide can enhance its effectiveness in preventing and controlling powdery mildew, rust, downy mildew, and rice blast, with both protective and therapeutic effects, and strong internal absorption conductivity.
Insecticides: undergo coupling reactions with pyrethroid alcohol and nicotine derivatives to synthesize pyrethroid esters and neonicotinoid insecticide intermediates. This type of insecticide is highly efficient, low toxic, and broad-spectrum, with specific effects on Lepidoptera and Homoptera pests. The propyl side chain can enhance insecticidal activity and shelf life.
Synthetic plant growth regulators
Methyl 2-bromopentanoate undergoes hydrolysis, decarboxylation, and amination reactions to produce α - aminobutyric acid derivatives and jasmonic acid analogues. This type of compound, as a plant growth regulator, can promote plant growth, flower bud differentiation, fruit enlargement, and enhance stress resistance. It is used for increasing yield and improving the quality of wheat, rice, vegetables, and fruit trees.
This section mainly refers to sources:
Douding.com Research on the application of 2-bromocarboxylic acid esters in pesticide synthesis two thousand and twenty-four
Gaide Chemical Network Explanation of the use of 2-bromopentanoic acid methyl ester pesticide intermediate two thousand and twenty-six
ChemBK. Synthesis route of 2-bromopentanoic acid methyl ester agricultural chemical two thousand and twenty-five
Frequently Asked Questions
Q: Why does methyl 2-bromovalerate often show partial racemization even under neutral storage conditions?
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A: The α-bromo ester structure is prone to slow, reversible enolization via trace moisture or weak bases. The enol intermediate is planar, so reprotonation can occur from either face, leading to gradual loss of optical purity over time, especially in liquid or solution state.
Q: Does methyl 2-bromovalerate readily undergo self-condensation or dimerization at room temperature?
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A: Under strictly anhydrous and neutral conditions, it is relatively stable. However, in the presence of trace alkoxides or strong organic bases, it can undergo Claisen-type self-coupling to form dimeric β-keto ester derivatives, which increases distillation residue and reduces yield.
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