Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 5-chlorovaleryl chloride cas 1575-61-7 in China. Welcome to wholesale bulk high quality 5-chlorovaleryl chloride cas 1575-61-7 for sale here from our factory. Good service and reasonable price are available.
5-Chlorovaleryl chloride, also known as 5-chlorohexanoyl chloride, is an organic compound. Colorless or pale yellow liquid, molecular formula C7H12Cl2O. It is insoluble in water and is a hydrophobic liquid, so its water solubility is relatively low. It has a higher boiling point and a lower melting point. It can be used as a chemical intermediate, widely used in the synthesis of other organic compounds, such as valerate oxalate and some other pharmaceutical intermediates, and also used in the preparation of liquid crystal basic materials and certain surfactants. Which can be used as a strong chlorinating agent and acylating agent in practical applications, so its physical properties are also of certain importance for these applications.
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Chemical Formula |
C5H8Cl2O |
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Exact Mass |
154 |
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Molecular Weight |
155 |
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m/z |
154 (100.0%), 156 (63.9%), 158 (10.2%), 155 (5.4%), 157 (3.5%) |
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Elemental Analysis |
C, 38.74; H, 5.20; Cl, 45.74; O, 10.32 |
Agrochemical Intermediate
Key Intermediate:5-Chlorovaleryl chloride serves as a foundational component in the production of pyrazole-based herbicides. Its chemical structure, particularly the presence of the acyl chloride group and the chlorine substituent, makes it highly reactive and suitable for further chemical modifications.
Mechanism of Action:These herbicides, once synthesized, inhibit the synthesis of very-long-chain fatty acids (VLCFAs). VLCFAs are essential for the formation of cell membranes in plants. By disrupting VLCFA synthesis, the herbicides effectively prevent the formation of intact cell membranes in weeds, leading to their death.
Enhancement of Herbicidal Activity and Environmental Stability
Chlorine Substituent:The chlorine substituent on the 5-chloropentanoyl chain plays a crucial role in enhancing the herbicidal activity of the final products. It may contribute to better binding affinity with target enzymes or receptors in weeds, thereby increasing the potency of the herbicide.
Environmental Stability:The presence of the chlorine atom also improves the environmental stability of the herbicides. This means that they are less likely to degrade rapidly in the environment, allowing for longer-lasting weed control and potentially reducing the need for repeated applications.
Fungicidal and Insecticidal Properties:Beyond herbicides, it can also participate in the synthesis of chlorinated heterocyclic compounds with fungicidal or insecticidal properties. These compounds are designed to target specific pests or pathogens, offering an additional layer of crop protection.
Target Specificity:The 5-chloropentanoyl group in these compounds contributes to their target specificity. It may help the compounds to bind more selectively to their intended targets, reducing off-target effects and improving their overall efficacy and safety.
Polymer Modifiers
Reaction Mechanism
When 5-chlorovaleryl chloride reacts with a hydroxyl-terminated polymer, the acyl chloride group undergoes a nucleophilic acyl substitution reaction with the hydroxyl group of the polymer. This results in the formation of an ester linkage and the release of a hydrogen chloride molecule. The resulting chlorinated ester contains the 5-chloropentanoyl moiety, which contributes to the desired properties of the polyurethane.
Improved Flame Retardancy
The introduction of chlorine atoms into the polyurethane structure through the reaction with it enhances its flame retardancy. Chlorine is a known flame retardant element, as it can interfere with the combustion process by forming stable chlorine-containing radicals that inhibit the chain reactions of combustion. This makes the polyurethane less flammable and more resistant to fire.
Enhanced Hydrophobicity
The chlorinated esters formed from the reaction with polyols also contribute to the hydrophobicity of the polyurethane. The presence of chlorine atoms in the polymer chain reduces the polarity of the material, making it less likely to absorb water or moisture. This property is particularly valuable in applications where the polyurethane needs to maintain its integrity and performance in wet or humid environments.
Polyurethanes synthesized with chlorinated esters derived from it are indeed widely used in industries where flame retardancy and hydrophobicity are essential. Here's a detailed overview of their applications in various sectors:
1. Construction Materials
Insulation: In the construction industry, polyurethanes are used as insulation materials due to their excellent thermal insulation properties. The addition of chlorinated esters derived from it enhances the flame retardancy of these materials, making them suitable for use in buildings where fire safety is a concern.
Waterproofing: The hydrophobicity imparted by the chlorinated esters makes these polyurethanes ideal for waterproofing applications, such as in roofing membranes, basement waterproofing, and tunnel linings.
2. Automotive Parts
Interior Components: Polyurethanes are used in automotive interiors for their durability, comfort, and aesthetic appeal. The flame retardancy and hydrophobicity of polyurethanes synthesized with chlorinated esters make them suitable for use in seat cushions, headliners, and door panels, where fire safety and moisture resistance are important.
Under-the-Hood Applications: These polyurethanes can also be used in under-the-hood automotive components, where they need to withstand high temperatures and resist moisture and chemicals.
3. Electrical Insulation
Wiring and Cables: Polyurethanes with enhanced flame retardancy and hydrophobicity are used in electrical wiring and cables to provide insulation and protection against electrical fires and moisture damage.
Electrical Enclosures: They are also used in electrical enclosures and switchgear to prevent the spread of fire and protect electrical components from moisture and corrosion.
4. Protective Coatings
Anti-Corrosion Coatings: The hydrophobicity of these polyurethanes makes them suitable for use as anti-corrosion coatings on metal surfaces, where they can prevent moisture and corrosive substances from reaching the underlying substrate.
Fire-Resistant Coatings: In applications where fire resistance is critical, such as in buildings, ships, and aircraft, polyurethanes synthesized with chlorinated esters can be used as fire-resistant coatings to protect surfaces from fire damage.
Experimental Research Case
The experiment began with the preparation of a reaction mixture by cooling a solution of pyridine in ether to −10 °C. Hydrogen peroxide (30%) was added dropwise, maintaining the temperature between −5 and 10 °C. The mixture was stirred at 0 °C for 2 hours, then neutralized with 10% sulfuric acid. The organic layer was separated, washed with 10% sodium carbonate solution and water, and dried over anhydrous sodium sulfate. The crude product was purified via column chromatography using a hexane/ethyl acetate gradient, yielding a high-purity intermediate for herbicide synthesis.
Another study highlighted its role in the synthesis itself using a one-pot method. The process involved reacting 1,4-dichlorobutane with sodium cyanide in the presence of a phase-transfer catalyst, followed by hydrolysis and acylation with thionyl chloride. This method efficiently produced the product alongside adipoyl chloride, with high yields and minimal waste.
5-Chlorovaleryl chloride (CAS: 1575-61-7), a key intermediate in organic synthesis, has evolved significantly since its discovery. Initially recognized for its reactivity as an acyl chloride, early studies focused on its role in esterification, amidation, and other functionalization reactions. The compound's potential as a pharmaceutical intermediate was highlighted in the 2010s, particularly in the synthesis of modified drug molecules. Its structural adaptability allowed for the introduction of chlorinated acyl groups, enhancing the bioavailability and efficacy of active pharmaceutical ingredients.
A breakthrough in synthetic methodology occurred in 2025, when a one-pot process was patented for the simultaneous production and adipoyl chloride from 1,4-dichlorobutane. This innovation streamlined manufacturing, reducing energy consumption and waste generation while improving yields. The method utilized phase-transfer catalysts and thionyl chloride, enabling efficient conversion of 5-chlorovaleric acid and adipic acid precursors into the target chlorides.
In pesticide chemistry, it gained prominence as a precursor for third-generation pyrazole herbicides, known for their high selectivity and low mammalian toxicity. Its integration into these formulations addressed the growing demand for environmentally friendly crop protection agents.
Safety and handling protocols have also advanced. The compound's volatile and irritant nature necessitated strict storage guidelines, including inert atmospheres and temperature control. Regulatory bodies classified it under UN3265, emphasizing its toxic and corrosive hazards.
Today, 5-chlorovaleryl chloride is produced at industrial scales by specialized manufacturers, with applications spanning pharmaceuticals, agrochemicals, and materials science. Its development history underscores the intersection of synthetic innovation, environmental stewardship, and industrial optimization, positioning it as a versatile tool in modern chemical synthesis.
Frequently Asked Questions
Is its molecular weight 155.02 or some other number? --There is a 'trap' hidden in precise weighing
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The molecular weights from different sources appear to be the same, but the number of significant digits is different. High precision liquid preparation should be based on the batch COA.
Each platform provides a molecular weight of 155.02 (or 155.022). Cold truth: The supplier explicitly reminds that "when preparing reserve solutions, it is necessary to use the molecular weight specific to the batch number on the product bottle label or Certificate of Analysis (COA)". Due to differences in isotope distribution and calculation, there may be hidden fluctuations in the third decimal place behind seemingly uniform numbers, which can have an impact on high-precision experiments.
Why does its boiling point fluctuate in different literature? --Pressure is the mastermind behind the scenes
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The boiling point at 0.2 hPa is 38-39 ° C, and at 0.15 mmHg it is also 38-39 ° C, but the actual pressure between the two is different.
The MSDS provides the condition that the boiling point is 38-39 ° C at 0.2 hPa (approximately 0.15 mmHg), while another data also indicates 38-39 ° C at 0.15 mmHg. Cold knowledge: The values of 0.2 hPa and 0.15 mmHg are close but not strictly equal, and this subtle difference, combined with factors such as purity and measurement methods, collectively creates the "Rashomon" of boiling point.
Besides conventional intermediates, what other 'hidden identities' does it have in the latest research in 2025?
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It was once used as a key starting material and a key intermediate for the synthesis of the heavyweight anticoagulant drug Apixaban.
Although this study was published in 2014, its process is still being optimized for use today. Research has shown that the intermediate of apixaban can be synthesized from nitroaniline and 5-chlorobenzoyl chloride through four steps of acylation cyclization and chlorination, with a total yield of 58.1% and a product purity of 99.5%. It is still a 'hidden hero' in the anticoagulant industry chain to this day.
In case of leakage, can conventional adsorbents be used for treatment? --Explosion proof is a key factor that is easily overlooked
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Anti static vacuum cleaners or wet brushes must be used for collection, and dry sweeping is strictly prohibited.
MSDS clearly requires that during leak handling, it should be collected using an anti electric vacuum cleaner or wet brush and disposed of in a sealed container. Cold mechanism: Its steam can accumulate in low-lying areas to form explosive concentrations (explosion limit 2.0-10.2%), and the static sparks generated by dry sweeping may ignite the steam - dealing with leaks is first for explosion prevention, followed by corrosion prevention.
Who is its true 'archenemy' in storage? --It's not air, it's water
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Extremely sensitive to moisture, it must be stored in an inert gas and sealed immediately after opening the bottle.
All MSDS consistently emphasize that storage conditions require inflation, moisture resistance, sensitivity to humidity, and avoidance of contact with moisture. Cold mechanism: It reacts with water to hydrolyze and produce 5-chlorovaleric acid and hydrogen chloride gas, which not only leads to a decrease in content, but also creates pressure and corrodes bottle caps in a closed container, causing internal damage to the entire bottle of reagents.
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