4-Propylphenylboronic acid, also known as propylphenylboronic acid or 4-n-propylphenylboronic acid, is an organic chemical substance that has wide applications in biochemical research and industrial production. CAS 134150-01-9, Molecular formula C9H13BO2, white or off white powder. Slightly soluble in water, soluble in ethanol, dimethylformamide, and dichloromethane. It is a weak acid that can react with some nucleophilic reagents, such as Grignard reagent, organolithium reagent, etc., to generate corresponding compounds. It can also undergo Suzuki Miyaura coupling reaction with another organic compound (such as aldehyde, ketone, acid, etc.) to synthesize organic molecules containing aromatic groups. Can be used to prepare 9,9'- anthracene derivatives 10,10' - di (4-propyl) phenyl-9,9 '- anthracene. Anthracene is a typical fluorescent material, which is often used as a precursor to improve its properties through various substituents. Anthracene derivatives have the advantages of high fluorescence quantum efficiency, good film-forming properties, and high stability. It can be used as a raw material for Suzuki coupling reaction, reacting with halogenated hydrocarbons and other compounds to generate organic compounds with specific structures.
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C.F |
C9H13BO2 |
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E.M |
164 |
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M.W |
164 |
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m/z |
164 (100.0%), 163 (24.8%), 165 (9.7%), 164 (2.4%) |
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E.A |
C, 65.91; H, 7.99; B, 6.59; O, 19.51 |
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Safety Precautions
4-Propylphenylboronic acid is an organic boron compound with the molecular formula C₉H₁₃BO₂. It appears as a white to off-white solid powder and has a pungent odor. The boronic acid group (-B(OH)₂) in its molecule endows it with unique chemical properties, which are widely applied in materials science, pharmaceutical synthesis, and biomedical fields. However, its potential health and environmental risks require users to strictly follow safety guidelines. The following is an explanation from five aspects: personal protection, operation norms, storage conditions, emergency handling, and waste management.
Personal Protective Equipment (PPE)
Respiratory Protection
When operating, wear a respirator or an N95-level mask to avoid inhaling dust or steam. In poorly ventilated environments (such as a sealed laboratory), use a positive pressure air respirator to ensure the cleanliness of the inhaled air.
Skin and Eye Protection
Wear chemical protective gloves (recommended as nitrile rubber or polyethylene, with a thickness of ≥ 0.3mm). Avoid direct skin contact. The lab coat should cover the entire body, with tight cuffs and collars to prevent material from seeping in. Wear a tightly fitting goggles or mask to prevent material from splashing into the eyes. If long-term operation is required, wear a full-face shield.
Other Protection
Avoid wearing clothing that easily adsorbs chemicals (such as wool or synthetic materials). It is recommended to wear cotton laboratory coats. After the operation, immediately wash hands and exposed areas to prevent material from being ingested through the mouth or skin.
Operating Procedures
Ventilation Requirements
All operations should be conducted in a fume hood or local exhaust system to ensure air circulation. The air velocity of the fume hood should be ≥ 0.5m/s, and the exhaust efficiency should be regularly tested. If operating in an open space, use a portable exhaust fan to maintain air flow.
Avoid Contact and Inhalation
It is strictly prohibited to touch the material directly with hands. Use specialized tools (such as medicine spoons or spatulas) to take samples. Conduct weighing in a fume hood to prevent dust dispersion. During the operation, do not eat, smoke, or apply makeup to prevent material from being ingested through the mouth or skin.
Dust Prevention Measures
When transferring or mixing materials, handle them gently to avoid vigorous shaking or tipping. If dust is generated, immediately stop the operation, cover with a damp cloth, and clean it. Do not use brooms or compressed air to sweep, as this may cause dust to fly.
Storage Conditions
Temperature and Humidity Control
Materials should be stored in a sealed, dry, and cool place, avoiding direct sunlight. It is recommended to store at a temperature of 2-8°C (short-term) or -20°C (long-term), with a relative humidity of ≤ 50%. If the material is in solution form, adjust the storage conditions according to the solvent properties (such as -80°C for acetonitrile solution).
Container Selection
Use glass bottles or polyethylene (PE) bottles for sealing storage. Avoid using metal containers (boric acid may react with metals). Containers should be labeled with the material name, CAS number (134150-01-9), storage conditions, and expiration date.
Isolation and Fire Prevention
Materials should be stored separately from oxidants (such as potassium permanganate), strong acids (such as hydrochloric acid), and food to prevent cross-contamination or accidental reactions. The storage area should be equipped with fire extinguishers (recommended carbon dioxide or dry powder extinguishers), and the "flammable solid" warning sign should be posted.
Emergency Handling
Skin Contact
Immediately remove contaminated clothing and rinse the affected area with plenty of water for at least 15 minutes. If the skin shows redness or pain, apply 2% sodium bicarbonate solution for wet compress and seek medical treatment. Contaminated clothing should be washed separately and not mixed with other clothing.
Eye Contact
Immediately rinse the eyes with flowing water or physiological saline for at least 15 minutes. Open the upper and lower eyelids during rinsing to ensure thorough cleaning. If wearing contact lenses, remove them before rinsing. Rinse immediately and seek medical attention to check for corneal damage.
Inhalation or Accidental Ingestion
If inhaling dust or steam, quickly transfer to an area with fresh air and keep the airway clear. If breathing stops, perform artificial respiration immediately and call for emergency assistance. If ingested, do not induce vomiting. Rinse with water and drink milk or egg white to protect the gastric mucosa and seek medical treatment.
Waste Management
Classification Collection
Wastes should be collected according to local environmental protection requirements, classified as solid waste, liquid waste, and contaminated containers. Solid waste should be sealed in double-layer plastic bags, and liquid waste should be poured into a dedicated recycling bucket and labeled with the "hazardous waste" sign.
Professional Handling
It is prohibited to directly discharge into sewers or soil. Such waste must be handled by institutions with qualifications for handling hazardous waste. Before disposal, a "Transfer Form for Hazardous Waste" needs to be filled out, documenting the type, quantity and handling method of the waste.
Packaging suggestions
The contaminated containers should be rinsed with clean water three times. The rinse water should be treated as waste. Empty containers should have their packaging destroyed (such as puncturing the bottle), to prevent misuse.
Summary
4-Propylbenzeneboronic acid is widely used in scientific research and industry, but its irritancy and potential health risks cannot be ignored. Users must strictly control the experiment from five aspects: personal protection, operation standards, storage conditions, emergency handling and waste management to ensure safety. In the future, with the development of green chemistry and precision medicine, the application potential of 4-Propylbenzeneboronic acid will be further released, but safety regulations will always be the prerequisite for its application.
Stability
Physical stability
4-propylphenylboronic acid exhibits excellent physical stability under dry and sealed conditions. Its melting point ranges from 89 to 97°C, indicating that it is in a solid state at room temperature and is not prone to phase changes. During storage, it should be avoided from high-temperature environments as its predicted boiling point is 299.1 ± 33.0°C, and high temperatures may lead to decomposition or volatilization. Additionally, this substance is sensitive to humidity and needs to be sealed for storage to prevent moisture absorption and caking, which could affect its usability.
Chemical stability
In terms of chemical stability, 4-Propylbenzhydrazide should be prevented from contact with strong oxidants (such as potassium permanganate), strong acids (such as hydrochloric acid), and metal ions to avoid oxidation, acidolysis, or coordination reactions. Storage in an inert atmosphere (such as nitrogen) can further extend its shelf life. Experiments have shown that at -20°C, its solution can be stably stored for 1 month; while at -80°C, the storage period can be extended to 6 months, indicating that low-temperature conditions are crucial for maintaining chemical stability.
Reactivity stability
In the Suzuki coupling reaction, 4-Propylbenzhydrazide exhibits high reactivity stability. The boronic acid group can efficiently form biphenyl compounds with halogenated aromatics under the action of a palladium catalyst, with a yield typically > 85%. The introduction of the propyl chain reduces molecular symmetry and enhances hydrophobicity, facilitating the optimization of reaction selectivity. However, during the reaction, strict control of temperature (80-100°C) and nitrogen protection is necessary to prevent the occurrence of side reactions.
Safety
Health hazards
The health impact of 4-propylphenylboronic acid mainly manifests in acute toxicity. Animal experiments show that its estimated acute oral toxicity value is 740 mg/kg, which is considered a low-toxic substance. However, direct contact may cause irritation to the skin and eyes, although it is not classified as corrosive or severely damaging to the eyes, protective equipment (such as gloves and goggles) still needs to be worn to reduce risks. Inhalation of dust or steam may cause respiratory tract irritation. During operation, ensure good ventilation.
Environmental hazards
The environmental impact of this substance has not been clearly classified yet. However, based on its chemical properties, it should be avoided from being directly discharged into water bodies or soil. Wastes need to be handled by professional institutions to prevent ecological pollution. Its biodegradability data is limited, but it is speculated that the degradation rate in natural environments is relatively slow, and it needs to be managed with caution.
Safety operation guidelines
When operating 4-propylboronic acid, strict safety guidelines must be followed. In terms of personal protection, one should wear laboratory coats, gloves and goggles to avoid skin and eye contact. The operation area should be kept well-ventilated to prevent dust accumulation. Storage should be sealed and placed in a dry, cool place, away from fire sources and oxidants. In case of emergency, if there is a leakage, use a wet cloth to cover and clean it, and do not use brooms or compressed air to sweep.
FAQ
1. Oxidative Homopolymerization Side Reaction Issue
Under certain Suzuki coupling conditions (such as the presence of oxygen and improper control of the palladium catalyst), does 4-propylbenzylboronic acid be more prone to undergo **oxidative self-coupling** compared to other substituted benzylboronic acids, generating a biphenyl by-product? Will the electron-donating effect of the propyl group exacerbate this side reaction by increasing the electron density of the benzene ring?
2. Irreversible Coordination with Palladium
Will the borate group of this compound undergo an **irreversible coordination or oxidative addition** with the zero-valent palladium precursor, forming an inactive palladium species, thereby causing the catalyst to "poison" and deactivate in certain ligand systems? Does the steric hindrance of the propyl group have any effect on inhibiting this process?
3. The Specificity of Thin Layer Chromatography (TLC) Detection
In the conventional silica gel TLC analysis, due to the boronic acid groups possibly interacting with the silanol groups on the silica gel plate, the spots may exhibit severe tailing or abnormally low Rf values in various developing agents. Are there reliable derivatization methods (such as esterification) or special developing systems that can clearly monitor the reaction process?
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