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N-Chlorosuccinimide, white powder or crystal. CAS 128-09-6, Molecular formula C4H4ClNO2. 1g of this product is dissolved in approximately 70ml of water, 150ml of ethanol, or 50ml of benzene, and slightly soluble in ether, chloroform, and carbon tetrachloride. 1: The aqueous solution is acidic (detected by litmus test) and has a melting point of 150-155 ℃. It can participate in various chlorination reactions, such as the double chlorination reaction with isonitrile to generate N-phenyldichloroimine compounds. In this reaction system, the substance generates chlorine free radicals, which first couple with isonitrile to form new free radicals. These new free radicals then further react with chlorine free radicals to ultimately produce double chlorination products. It is a convenient electrophilic addition and substitution reagent commonly used for the chlorination of sulfides, sulfones, and ketones, as well as for the synthesis of N-chloroamines.
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Chemical Formula |
C4H4ClNO2 |
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Exact Mass |
133 |
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Molecular Weight |
134 |
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m/z |
133 (100.0%), 135 (32.0%), 134 (4.3%), 136 (1.4%) |
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Elemental Analysis |
C, 35.98; H, 3.02; Cl, 26.55; N, 10.49; O, 23.96 |
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NCS is a white crystalline powder with the molecular formula C ₄ H ₄ ClNO ₂ and a molecular weight of 133.53. Its molecular structure contains an active chlorine atom, making it an important chlorinating agent, oxidizing agent, and reagent in organic synthesis.
The activity of NCS comes from the chlorine atom in its molecule, which can undergo electrophilic substitution or oxidation reactions with various organic compounds. Its core features include:
Selective chlorination: It can specifically replace α - H fatty acid chlorides to generate high-purity α - chlorinated fatty acids and their derivatives, without affecting the aromatic ring structure.
Mild oxidation: Primary alcohols can be oxidized to aldehydes, secondary alcohols to ketones, and diols to lactones, with mild reaction conditions and high yields.
Peptide bond cleavage: Selective cleavage of peptide bonds formed by tryptophan under acidic conditions, used for protein structure analysis.
Reagent stability: The solid form is stable, but it needs to be stored away from light and dry, and is sensitive to moisture.
Typical reaction example:
Synthesis of alpha chlorinated fatty acids:
NCS reacts with stearic acid to selectively chlorinate the alpha hydrogen, producing alpha chlorostearic acid, which is a key raw material for polyvinyl chloride (PVC) plasticizers.
Corey Kim oxidation reaction:
The combination of NCS and dimethyl sulfide (DMS) oxidizes alcohols to aldehydes or ketones under mild reaction conditions, making it suitable for complex molecular synthesis.
NCS is an essential intermediate in the pharmaceutical industry, and its chlorinated products are widely used in the synthesis of antibiotics, hormones, and anti-tumor drugs.
1. Antibiotic synthesis
Doxycycline and Methoxycycline:
NCS participates in the side chain chlorination of tetracycline antibiotics, introducing chlorine atoms through selective chlorination reactions to enhance the antibacterial activity of the drugs. For example, in the synthesis of tetracycline, NCS chlorinates the intermediate 6-methyltetracycline to produce the more active tetracycline.
Benzyl cephalosporin:
NCS is used for chlorination modification of cephalosporin core to enhance the stability of the drug against β - lactase, thereby increasing the antibacterial spectrum.
2. Hormonal drugs
Norethinyl ketone and 16 medroxyprogesterone:
NCS participates in the 17th chlorination of steroid hormones, producing the contraceptive active alkyne ketone. For example, in the synthesis of 16 medroxyprogesterone, NCS introduces 17 α - chloride atoms through chlorination reaction, significantly enhancing the oral bioavailability of the drug.
Chlorfenapyr:
NCS is used for the synthesis of estrogen analogues, regulating the binding ability of drugs and receptors through chlorination modification, and is used for the treatment of breast cancer and osteoporosis.
3. Anti tumor drugs
Bolemycin analogues:
NCS participates in the chlorination of bleomycin side chains to generate derivatives with stronger DNA cleavage activity, which are used to enhance the efficacy of chemotherapy drugs.
Case: In a certain pharmaceutical company's doxycycline production line, NCS was used as a chlorinating agent to increase the reaction yield from 65% of traditional chlorine gas method to 89%, while reducing the generation of by-products and significantly reducing purification costs.
Pesticide field: key raw materials from insecticides to herbicides
The chlorination products of NCS play an important role in the pesticide industry, and their derivatives have the characteristics of high efficiency and low toxicity.
1. Insecticides
Pyrethroid esters:
NCS participates in the synthesis of chlorpyrifos, introducing chlorine atoms through chlorination reaction to enhance the toxicity of the drug to the insect nervous system. For example, in the synthesis of cypermethrin, NCS chlorinates the intermediate cypermethrin to produce the more active cypermethrin.
Aminomethyl esters:
NCS is used for side chain chlorination of carbapenem to enhance its killing effect on aphids and leafhoppers.
2. Weedkillers
Chlorophenoxyacetic acid:
NCS participates in the synthesis of 2,4-D (2,4-dichlorophenoxyacetic acid) and generates highly efficient herbicides through selective chlorination, which are widely used for field weeding of crops such as corn and wheat.
Sulfonylurea:
NCS is used for the synthesis of chlorsulfuron, enhancing the inhibitory effect of the drug on weed acetyl lactate synthase (ALS) through chlorination modification, achieving low-dose and efficient weed control.
Case: In the 2,4-D production line of a pesticide enterprise, NCS replaced the traditional chlorine gas method, shortening the reaction time from 12 hours to 4 hours while reducing exhaust emissions, which meets the requirements of green chemistry.
Dyes and Materials Science: From Functional Modification to Performance Enhancement
The application of N-chlorosuccinimide in the fields of dyes and materials mainly focuses on the functionalization of molecular structure and the improvement of material surface properties.
1. Dye synthesis
Reactive dyes:
NCS participates in the synthesis of vinyl sulfone reactive dyes, introducing chlorosulfonic acid groups through chlorination reaction to enhance the binding ability between dyes and fibers. For example, in the synthesis of reactive black K-BR, NCS chlorinates the intermediate to generate more reactive dye molecules.
Fluorescent dyes:
NCS is used for side chain chlorination of coumarin fluorescent dyes, achieving a red shift in fluorescence wavelength by adjusting the molecular conjugation system, for use in biological imaging and fluorescent labeling.
2. Material surface treatment
Polyester fiber modification:
NCS, as a treatment agent, can enhance the acceptance of dyes and printing inks by polyester fibers. For example, treating the fiber surface with NCS solution before dyeing polyester fabric significantly improves the dye uptake and color fastness.
Rubber additives:
NCS participates in the synthesis of antioxidant 4010NA, introducing chlorine atoms through chlorination reaction to improve the ozone resistance and heat aging resistance of rubber.
Case: In the polyester dyeing process of a textile enterprise, the introduction of NCS pretreatment resulted in a 30% increase in dyeing depth (K/S value) and a 15% reduction in dye usage, significantly reducing production costs.
Industrial disinfection and water treatment: an efficient and broad-spectrum sterilization solution
NCS is widely used in fields such as medical device disinfection, food processing, and water treatment due to its rapid and broad-spectrum bactericidal ability.
1. Disinfection of medical devices
Endoscope cleaning:
NCS is prepared into 2% aqueous solution, and the endoscope is soaked and sterilized, which can effectively kill hepatitis B virus (HBV) and human immunodeficiency virus (HIV), and is non corrosive to metals and plastics.
Sterilization of surgical instruments:
The combination of NCS and hydrogen peroxide generates active chlorine and free radicals, achieving low-temperature rapid sterilization and suitable for the disinfection of precision instruments.
3. Water treatment
Swimming pool disinfection:
NCS replaces traditional chlorine gas, reduces the generation of chloramines, lowers the "chlorine odor" and eye irritation, while maintaining an effective chlorine concentration of 0.5-1.0 ppm.
Industrial circulating water:
The combination of NCS and sodium bromide generates active bromine, effectively controlling the growth of Legionella and algae in the cooling tower.
Case: In the disinfection process of a dairy factory, after replacing sodium hypochlorite with NCS, the microbial contamination rate decreased from 12% to 0.5%, while reducing equipment corrosion and extending pipeline service life.
2. Food processing
Disinfection of dairy products:
NCS is used for circulating disinfection of milk pipelines, which can kill Listeria and Salmonella, and the residual chlorine content is less than 0.1 ppm, meeting food safety standards.
Fruit and vegetable preservation:
Soaking in NCS solution can inhibit mold growth and extend the shelf life of apples and strawberries.
N-Chlorosuccinimide exhibits unique reactivity in organic synthesis and can achieve various characteristic transformations.
1. Identification of primary, secondary, and tertiary alcohols
Reaction principle:
NCS reacts with alcohols to produce products of different colors: primary alcohols produce blue, secondary alcohols produce green, and tertiary alcohols do not react. This reaction is based on the difference in the oxidation ability of chlorine atoms towards hydroxyl groups.
Application scenarios:
Used for quickly identifying the structure of unknown alcohols and assisting in the design of organic synthesis routes.
2. Chlorination of sulfides and sulfones
Reaction example:
NCS chlorinates dimethyl sulfide to dimethyl sulfoxide (DMSO), which is an important polar non proton solvent. Mild reaction conditions and high yield.
Industrial value:
DMSO is widely used in the fields of medicine, electronics, and chemical engineering, and the NCS method is the key technology for its large-scale production.
3. Synthesis of allylamine and B, R-unsaturated amino acids
Reaction mechanism:
NCS achieves allyl chlorination through free radical mechanism, generating allyl amine derivatives, which are important intermediates for anti-tumor drugs and antiviral agents.
case
In the synthesis of a certain antiviral drug, NCS participates in the chlorination of allylamine, generating key intermediates and shortening the reaction steps from 5 to 3, resulting in a 25% increase in overall yield.
Synthesis of N-chlorosuccinimide:
An optimized preparation method of it, which is characterized in that the preparation steps are:
(1) Put succinic acid and ammonia water in a reaction kettle and stir them until they fully react, keeping the reaction temperature at 20~25 ℃;
(2). Put the reaction solution of succinic acid and ammonia in a distillation kettle, and dehydrate it at 275~290 ℃ to obtain succinimide solid;
(3) Add succinimide solid into glacial acetic acid aqueous solution and stir until it is completely dissolved;
(4). Cool the mixed solution of succinimide and glacial acetic acid to below 0 ℃, maintain this temperature, add sodium hypochlorite solution, and stir for 0.5~1.5 hours to obtain the mixed solution;
(5). The mixed solution is filtered and washed to neutral to obtain white solid powder, which is the finished product of NCS.
Frequently Asked Questions
Why is it favored among many chlorinated reagents for its "mildness and selectivity"?
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Its "mildness" stems from its stability in the solid state and gradual release of active chlorine only after dissolving in a solvent. Its selectivity is reflected in the ability to achieve specific chlorination of electron rich olefins, aromatic rings, etc; Sensitive groups such as alcohol hydroxyl groups can be oxidized under appropriate conditions without damaging their structure.
Apart from conventional chlorination, what is a very unique "oxidation" application of it in synthetic chemistry?
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Used to directly oxidize aldehydes to acyl chlorides, which is a key intermediate in synthesis. For example, the reaction between benzaldehyde and NCS can generate benzoyl chloride, which has mild reaction conditions and avoids the intensity and side reactions of traditional methods such as oxalyl chloride.
Why is it often used in combination with "catalytic" acids or Lewis acids, and what does this change?
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NCS itself has limited chlorination activity. Adding catalytic amounts of proton acid or Lewis acid (such as sulfuric acid, scandium trifluoromethanesulfonate) can significantly enhance its electrophilicity, activate inert substrates, and even achieve complex selective chlorination that traditional methods cannot achieve.
How cleverly does it play the role of a "structural installer" in the total synthesis of natural products?
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By utilizing its selectivity, chlorine atoms can be precisely introduced into specific positions of complex molecular skeletons, which can serve as key synthetic handles for subsequent cross coupling, elimination, or nucleophilic substitution reactions, thereby efficiently constructing the final target molecule.
How is the "by-product" succinimide recycled and utilized in industrial production, and what green chemistry ideas are reflected?
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The succinimide generated after the reaction can be recovered by simple filtration and reused as a raw material for the synthesis of NCS. This "reagent byproduct raw material" recycling model reduces waste emissions and complies with the atomic economy principle of green chemistry.
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