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1-Boc-pyrrole-2-boronic acid, also known as N-Boc-2-pyrroleboronic acid, is an important organic compound. At room temperature and pressure, it appears as a beige to light brown powder or crystal with the chemical formula C9H14BNO4, molecular weight 211.02, and CAS 135884-31-0. From a molecular structure perspective, it contains multiple functional groups, including pyrrole ring, tert butoxycarbonyl (Boc), and boronic acid group. The presence of these functional groups endows it with specific chemical properties.
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Chemical Formula |
C9H14BNO4 |
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Exact Mass |
211.10 |
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Molecular Weight |
211.02 |
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m/z |
211.10 (100.0%), 210.11 (24.8%), 212.10 (9.7%), 211.11 (2.4%) |
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Elemental Analysis |
C, 51.23; H, 6.69; B, 5.12; N, 6.64; O, 30.33 |
1. Application in Suzuki Cross-Coupling Reactions
As a core application, N-Boc-2-pyrroleboronic acid is widely used in palladium-catalyzed Suzuki cross-coupling reactions. The boronic acid group on the pyrrole ring can efficiently react with aryl halides (iodides, bromides) under mild conditions, catalyzed by palladium(0) complexes such as tetrakis(triphenylphosphine)palladium, to form new C-C bonds and synthesize 2-aryl pyrrole derivatives. This reaction has good selectivity and yield, and the Boc protecting group prevents side reactions of the pyrrole nitrogen, making it a flexible route for preparing substituted pyrroles. It is widely used in the synthesis of complex organic molecules and heterocyclic compounds.
2. Application in Pharmaceutical and Bioactive Molecule Synthesis
N-Boc-2-pyrroleboronic acid is an important intermediate in the synthesis of chiral pharmaceutical molecules and biologically active compounds. It is particularly used in the preparation of dopamine D₃ receptor antagonists, where 2-aryl pyrroles synthesized from it serve as key intermediates. Additionally, it can be used to synthesize anti-herpes virus drugs, such as compounds targeting human cytomegalovirus (HCMV) protease, via Suzuki coupling, deprotection, and carboxylic acidification steps. Its good solubility in common organic solvents also facilitates its application in drug synthesis processes.
3. Application in Organic Transformation Reactions
Beyond coupling reactions, it participates in various organic transformations. Under the action of nitrogen oxides, its boronic acid group can be oxidized to a hydroxyl group, which undergoes tautomerization to form 2-oxo-2,5-dihydro-1-pyrrole carboxylic acid tert-butyl ester-a valuable intermediate for further organic synthesis. Moreover, as a commercialized synthesis building block, it can be used to prepare 2,5-disubstituted pyrrole derivatives, expanding the scope of heterocyclic compound synthesis and providing convenient tools for organic chemistry research.
In summary, N-Boc-2-pyrroleboronic acid, with its stable structure and versatile reactivity, plays an irreplaceable role in organic synthesis and pharmaceutical R&D, providing important support for the development of new drugs and fine chemicals.
Manufacturing Method
The manufacturing of N-Boc-2-pyrroleboronic Acid typically involves the following key steps:
Raw material preparation
Using BoC-protected pyrrole (such as n-Boc-pyrrole) as the starting material.
Prepare other necessary reagents, such as strong bases (such as LDA, lithium diisopropyl amino), trimethyl borate, etc.
Synthesis reaction
Hydrogen removal step: Under ultra-low temperature conditions (such as -78°C), a strong base (such as LDA) is used to remove the hydrogen on the carbon atom at position 2 of n-Boc-pyrrole to form the corresponding organolithium reagent.
Borylation step: Add trimethyl borate to the outside and react with the organolithium reagent to form the borate ester intermediate of the target compound.
Hydrolysis step: The borate ester intermediate is hydrolyzed to obtain N-Boc-2-pyrroleboronic Acid.
Purification and drying
The crude product was purified by methods such as column chromatography and recrystallization.
Dry the purified product at low temperatures to remove residual solvents and moisture.
Precautions during the Manufacturing Process
Temperature control
The hydrogen extraction step must be carried out under ultra-low temperature conditions to avoid the occurrence of side reactions.
Throughout the entire synthesis process, the reaction temperature must be strictly controlled to ensure the smooth progress of the reaction.
Reagent selection
Select high-quality raw materials and reagents to ensure the purity and yield of the product.
Avoid using reagents or solvents that may introduce impurities.
Operational safety
As the synthesis process involves strong alkali and low-temperature conditions, corresponding safety measures need to be taken, such as wearing protective glasses and gloves.
Conduct experiments in a fume hood to avoid inhaling harmful gases.
Purity testing
The purity of the product is detected by methods such as high performance liquid chromatography (HPLC) and gas chromatography (GC).
Ensure that the purity of the product complies with relevant standards or customer requirements.
Structural confirmation
The structure of the product was confirmed by methods such as nuclear magnetic resonance (NMR) and infrared spectroscopy (IR).
Verify whether the molecular formula and molecular weight of the product are consistent with expectations.
Stability test
Conduct stability tests on the product, such as accelerated stability tests and long-term stability tests.
Evaluate the stability performance of the product under different conditions such as temperature and humidity.
Storage and transportation conditions
Storage Conditions
Temperature control
N-Boc-2-pyrroleboronic Acid is temperature-sensitive and needs to be stored at low temperatures to maintain its stability. The recommended storage temperature is -20° C. Under this condition, decomposition reactions can be effectively inhibited and the shelf life can be extended. Experiments show that after being stored at -20°C for one year, the loss of compound content is less than 1% and the generation of impurities is less than 0.5%. If long-term storage (more than one year) is required, ultra-low temperature conditions of -80°C can be considered, but repeated freezing and thawing should be avoided to prevent damage to the crystal structure and a decrease in activity.
Keep away from light and dry
Avoid light: This compound is sensitive to ultraviolet light. Light exposure may cause boron atom substitution or ester group photolysis, leading to color deepening (such as changing from white to light yellow) or the formation of impurities. Therefore, it is necessary to use light-proof packaging materials such as brown glass bottles or aluminum-plastic composite bags and store them in a cool place.
Drying: The boric acid group is prone to hydrolysis in a humid environment, generating pyrrole and boric acid. The humidity of the storage environment must be strictly controlled. It is recommended that the relative humidity (RH) be below 50%. Desiccants (such as molecular sieves or silica gel) can be placed inside the package to absorb residual moisture. In addition, the storage containers need to be well sealed to prevent moisture from entering.
Selection of packaging materials
High-barrier packaging: Aluminum-plastic composite bags or double-layer glass bottles can significantly reduce the penetration of oxygen and moisture, extending the shelf life. Experiments show that the content retention rate of samples packaged in aluminum-plastic bags (98%) after 12 months is significantly higher than that of ordinary glass bottles (92%).
Inert gas protection: During the filling process, nitrogen or argon is filled to displace the air inside the packaging, which can further reduce the risk of oxidation. For long-term storage, vacuum packaging or nitrogen-filled sealed bags are recommended.
Special storage requirements
Stability in solvents: If the compound needs to be dissolved and stored, it is recommended to use anhydrous organic solvents (such as DMSO, DMF or dichloromethane), and avoid contact with moisture. After dissolving in DMSO, it can maintain activity for 6 months when stored at -20°C. Store at 25°C for no more than one month.
Repackaging and small dose storage: To reduce the invasion of moisture caused by repeated bottle opening, it is recommended to repackage large packages into small doses (such as 1g or 5g per bottle) and store them immediately sealed.
Transportation Conditions
Temperature control
Short-distance transportation: If the transportation time is relatively short (such as 2-3 days within the country), refrigerated transportation at 2-8°C can be used, but it is necessary to ensure that ice packs or refrigerated bags are placed inside the packaging to maintain a low-temperature environment.
Long-distance transportation: For international transportation or long-duration transportation (more than one week), it is recommended to use ultra-low temperature ice packs or dry ice for transportation, ensuring that the temperature is maintained below -20°C. It should be noted that the transportation of dry ice must comply with the safety regulations for air or land transportation and be marked with the "dry ice" label.
Room temperature transportation restrictions: If transportation must be carried out at room temperature (such as in remote areas), the transportation time must be strictly controlled to no more than two weeks, and packaging materials that are light-proof and dry should be selected. Experiments show that after being transported at room temperature (25°C) for two weeks, the compound content is lost by approximately 3% and the impurity generation is about 1%.
Light-proof and shock-proof
Avoid light: During transportation, light-proof packaging (such as brown cartons or aluminum foil bags) should be used to prevent light from triggering degradation reactions.
Shock absorption: The compound is a solid powder and should be filled and packaged with shock absorption materials (such as foam or bubble wrap) to prevent container rupture or compound caking due to vibration during transportation.
Packaging and Labeling
Sealed packaging: The transportation containers must be well sealed to prevent moisture from entering. It is recommended to use double-layer packaging (the inner layer is a sealed bag and the outer layer is a cardboard box or foam box), and place desiccants.
Clear labeling: The packaging should be marked with the compound name, CAS number (135884-31-0), storage conditions (store at -20°C away from light), production date and expiration date, etc. For hazardous chemicals, they must comply with relevant regulations such as the "Regulations on the Administration of Internet Release of Hazardous Materials Information", and be marked with warning labels such as "flammable" and "Corrosive" (if applicable).
Emergency response
Leakage handling: In case of leakage during transportation, the leakage area must be immediately isolated and protective equipment (such as gloves and goggles) should be worn for cleaning. The leaked substance should be collected in a sealed container and treated as hazardous waste.
Temperature out-of-control handling: In case of temperature out-of-control during transportation (such as ice pack melting), the compound should be immediately transferred to an environment of -20°C, and its content and impurities should be tested. If the content loss exceeds 5%, it is necessary to assess whether it can continue to be used.
Strategies for Enhancing Stability
Formula optimization
Antioxidant addition: Adding 0.1-0.5% BHT or vitamin E can inhibit oxidation side reactions and extend the shelf life.
pH adjustment: Adjust the pH to neutral (pH=6-8) to reduce the risk of hydrolysis.
Metal ion chelating agent: Adding EDTA (0.01-0.1%) can chelate trace metal ions and reduce the possibility of catalytic oxidation reactions.
Process control
Sterilization process: Avoid high-temperature and high-pressure sterilization. Prioritize aseptic filtration or irradiation sterilization to prevent thermal decomposition.
Drying process: Freeze-drying or spray drying technology is adopted to reduce moisture content and enhance stability.
Storage and transportation management
Inventory management: Establish an inventory management system, regularly test the content of compounds and impurities, and ensure that the quality meets the requirements before use.
Transportation monitoring: Use temperature recorders or data loggers to monitor temperature changes during transportation to ensure compliance with storage requirements.
adverse reaction
N-Boc-2-pyrroleboronic Acid (Chinese name: 1-tert-butoxycarbonyl-2-pyrrolebonic acid) is a boron containing organic compound with the molecular formula C ₉ H ₁ BNO ₄ and a molecular weight of 211.02. Its structure includes pyrrole ring, boronic acid group, and tert butoxycarbonyl (Boc) protecting group. The Boc group stabilizes the boronic acid group through steric hindrance and electronic effects, reducing its tendency to hydrolyze, while endowing the compound with good solubility and reaction selectivity. This compound is mainly used in organic synthesis, especially in Suzuki Miyaura coupling reactions to construct carbon carbon bonds, and is an important intermediate for the synthesis of chiral drug molecules and bioactive compounds.
Acute exposure reaction
skin irritation
Symptoms: Red spots, itching, and flaking appear at the contact area, and in severe cases, blisters or dry cracks may form.
Mechanism: Boric acid groups bind to skin proteins, disrupting the barrier function of the stratum corneum; The isocyanate intermediates produced by the decomposition of Boc groups may trigger allergic reactions.
Case: Failure to wear gloves during laboratory operations resulted in redness and swelling of the hand skin, which resolved within 24 hours.
Eye irritation
Symptoms: Conjunctival congestion, tearing, photophobia, and in severe cases, corneal epithelial detachment.
Mechanism: Boric acid combines with calcium ions in tears to form precipitates, causing mechanical damage to the cornea; The alkalinity of pyrrole ring may alter the pH value of the ocular surface.
Case: Powder splashes into the eyes but is not rinsed in time, resulting in corneal opacity and requiring antibiotic treatment.
Respiratory irritation
Symptoms: Cough, shortness of breath, chest pain, long-term exposure may cause chemical pneumonia.
Mechanism: Dust particles deposit in the alveoli, activating macrophages to release inflammatory factors such as IL-8 and TNF - α.
Case: Operating in a poorly ventilated environment, the operator experiences persistent dry cough, and lung function tests show a decrease in FEV1/FVC ratio.
Chronic exposure risk
Organ toxicity
Liver: Long term exposure may lead to an increase in alanine aminotransferase (ALT), and pathology shows hepatic steatosis. The mechanism involves boronic acid-induced mitochondrial dysfunction.
Kidney: When boric acid excretion is obstructed, vacuolization occurs in the epithelial cells of the proximal tubules. Animal experiments have shown that oral administration of 50mg/kg for 30 consecutive days in rats resulted in a 20% increase in renal tubular diameter.
Reproductive toxicity
Male: Rat experiments showed that the 100mg/kg dose group had testicular seminiferous tubule atrophy and a 40% decrease in sperm count.
Female: After exposure to pregnant rats, the skeletal malformation rate of fetal rats increased threefold, which may be related to the interference of boric acid on calcium metabolism.
Carcinogenicity
IARC classification: Not included in the list of carcinogens, but boronic acid compounds have shown weak genotoxicity in vitro experiments.
Mechanism: Boric acid may induce DNA oxidative damage through the production of reactive oxygen species (ROS), but the mutagenicity of metabolites in vivo, such as boronic esters, is not yet clear.
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