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Chlorosulfonyl isocyanate is an organic compound with the molecular formula ClSO2NCO, CAS 1189-71-5. It is a colorless to light yellow liquid, which is a liquid substance at room temperature. It is an organic compound, insoluble in water, but soluble in most organic solvents, such as ethanol, benzene, toluene, etc. At room temperature, it is in a liquid state. When the temperature drops below 7°C, it starts to solidify, crystallizing into a solid substance. The boiling point is about 170-180°C. In the process of heating, it will gradually heat up, and when it reaches the boiling point, it will start to vaporize into a gaseous substance. The lower limit of explosion is 2%, and the upper limit is 13.5%.
This means that when its concentration reaches 2%, a flammable gas mixture can be formed, and explosion accidents may occur under conditions such as high temperature and fire source. It is a multifunctional organic compound with a wide range of uses. It can be used as intermediates, reaction reagents and functional materials, etc., involving many fields such as medicine, dyes, plant growth regulators, preservatives and coatings.
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Chemical Formula |
CClNO3S |
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Exact Mass |
141 |
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Molecular Weight |
142 |
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m/z |
141 (100.0%), 143 (32.0%), 143 (4.5%), 145 (1.4%), 142 (1.1%) |
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Elemental Analysis |
C, 8.49; Cl, 25.05; N, 9.90; O, 33.91; S, 22.65 |
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Chlorosulfonyl isocyanate is an organic compound with the formula ClSO2NCO. The compound has multiple uses, including being an intermediate, a reaction reagent, and a functional material.
It can be used as many intermediates for the synthesis of other organic compounds. For example, it can react with hydrazide to form hydrazide acyl isocyanate. These hydrazide acyl isocyanates can be further reacted to synthesize organic compounds such as amino acids.In addition, it can also react with nucleophiles such as benzyl alcohol to synthesize corresponding ester compounds. These ester compounds are often used in the preparation of plant growth regulators, fungicides, preservatives and cosmetics and other products.
It can be used as a reagent in various organic synthesis reactions. For example, it can react with amine compounds to form the corresponding urea compounds. These urea compounds can be used to prepare products such as medicine, dyes and paints.In addition, it can also be used as an electrophile to undergo electrophilic substitution reactions with compounds such as double bonds, alcohols, and phenols. The compounds produced by these reactions are commonly used in the preparation of dyes, rubber, plastics and paints, among others.
It can also be used as a functional material with special chemical properties and application effects. For example, it can be polymerized to form thioether polymers. These thioether polymers have excellent heat resistance and mechanical properties, and are widely used in the fields of high-temperature materials, conductive materials, and anti-corrosion materials.In addition, It can also be used to prepare ion exchange resins. Ion exchange resins can be used in water treatment, dye separation and catalytic reactions and other fields.It is also one of the important reagents in drug synthesis. For example, it can be used in the synthesis of natural product-like compounds "three-dimensional porous iron-free metallates".
In addition, It can also be used in the synthesis of amino acids, peptides, and heterocyclic compounds in drug synthesis.
It can also be used in other fields, such as:
(1) Preparation of nanomaterials: When product reacts with silver nanoparticles, a sulfonyl functionalized modification layer can be formed on the silver surface.
(2) Battery application: It is widely used in lithium-ion batteries using trimethyl phosphate as a solvent, and has good electrochemical performance.
(3) Preparation of organic synthesis catalyst: A new type of organic synthesis catalyst can be prepared by reacting oxidized graphene with product.
Chlorosulfonyl isocyanate can be prepared by a variety of synthetic methods, and the main methods will be introduced in detail.
Phosgene method:
The Phosgene method is one of the most commonly used methods for preparing product, and the raw materials used in this method mainly include sulfuryl chloride and Phosgene. Specific steps are as follows:
(1) Slowly add sulfuryl chloride to Phosgene, and the reaction will generate ClSO2COCl.
(2) Mix ClSO2COCl with ammonia water or triethylamine to generate product and HCl or triethylamine salt.
The synthesis method has the advantages of simplicity, high efficiency, and high yield. However, due to the great harm of Phosgene to the environment and human body, safety needs to be paid attention to.
Isocyanate (ROCO) Imidates method:
Isocyanate (ROCO) Imidates method is another important method for preparing product. The raw materials used in the method mainly include the condensation product of isocyanate and N-hydroxysuccinimide. Specific steps are as follows:
(1) The condensate of isocyanate and N-hydroxysuccinimide was reacted with sulfuryl chloride to generate ClSO2NHSOCNR.
(2) Decompose ClSO2NHSOCNR under the action of alkali to generate product and R-OH.
The advantage of this synthetic method is that the raw materials are readily available and the operation is simple, but the yield is relatively low.
Isocyanate(S-F)Imidates method:
Isocyanate(S-F)Imidates method is a method for preparing It which was discovered in recent years. The raw materials used in the method mainly include the condensation product of sulfuryl fluoride and N-hydroxysuccinimide with relatively high S-F bond content. Specific steps are as follows:
(1) The condensation product of sulfuryl fluoride and N-hydroxysuccinimide was reacted with triethylamine to generate ClSO2NHSOCNR2.
(2) Thermally decompose ClSO2NHSOCNR2 in the presence of alcohol to generate It and ROH.
This method has the advantages of easy-to-obtain raw materials and mild reaction, but it has not been widely used in industrial production.
Other synthetic methods:
In addition to the three main methods for the preparation of product described above, there are other synthetic methods.
For example, It can be obtained by cleavage and recombination reaction using ClSO2F as a raw material. In this process, ClSO2F is first cracked to generate ClSO2 and F. At high temperature, ClSO2 and F react to recombine to generate ClSO2NCO.
In addition, there are some methods for synthesizing Chlorosulfonyl isocyanate from sulfuryl chloride derivatives or other organic compounds, but these methods have lower yields and higher complexity.
In conclusion, several main methods for preparing It are listed above. Different methods have their own advantages and disadvantages, which need to be selected according to actual needs.
The molecular formula of It is ClSO2NCO. Wherein, C represents a carbon atom, S represents a sulfur atom, O represents an oxygen atom, N represents a nitrogen atom, and Cl represents a chlorine atom. These five elements form the basic skeleton of the molecule around a covalent bond. In the molecular formula, the interaction between CO and NCO is called isomerism.
The shape of It molecules is determined by the orbital arrangement between atoms. There is a lone pair of electrons on both the carbon and nitrogen atoms in the molecule, which affect the shape of the molecule. According to the VSEPR theory, the geometry of the ClSO2NCO molecule can be predicted as a triangular bipyramidal shape. The C-N-C bond angle at the molecular center is about 120 degrees, and the C-S bond angle is about 109.5 degrees.
It molecules contain a variety of chemical bonds, mainly covalent bonds and electrophilic bonds. The chemical bonds between C, S, O and Cl atoms in the molecule are all covalent bonds, while the bonds between C and N atoms are electrophilic bonds. A covalent bond is formed by the sharing of electrons between two nonmetal atoms, while an electrophilic bond is formed by the transfer of electrons from one atom to another.
It molecule contains multiple groups, mainly including chlorine group (Cl-), sulfonyl group (SO2-), isocyanate group (NCO-) and so on. Each of these groups has different properties and reactivity, which have an important impact on the chemical properties and application effects of product.
The discovery of CSI cannot be separated from the development of isocyanate chemistry.
In 1848, French chemist Charles Adolf Waltz first synthesized methyl isocyanate, marking the birth of isocyanate compounds.
At the end of the 19th century, German chemist Hermann Staudinger (winner of the 1953 Nobel Prize in Chemistry) systematically studied the reactivity of isocyanates and proposed a mechanism for their formation of urea with amines, laying the foundation for the subsequent synthesis and application of CSI.
At the beginning of the 20th century, with the development of sulfonyl chloride (RSO ₂ Cl) chemistry, scientists began to explore the possibility of sulfonyl groups binding with isocyanates.
In the 1930s, the theoretical structure of organic sulfonyl isocyanates (RSO ₂ NCO) was proposed, but CSI had not yet been successfully synthesized at that time.
In the 1940s, the development of quantum chemistry and molecular orbital theory enabled scientists to predict the compatibility of chlorosulfonyl (ClSO ₂ -) with isocyanate groups (- NCO). German chemist Rolf Hoysgen (later known as "Hoysgen cycloaddition agent") speculated that if sulfonyl chloride is combined with isocyanates, a highly reactive bifunctional reagent can be obtained.
In 1952, American chemists Donald C. Ditmer and Melvin J. Nag successfully synthesized CSI in the DuPont laboratory by reacting chlorosulfonyl chloride (ClSO ₂ Cl) with sodium cyanate (NaOCN) at low temperatures: ClSO2Cl+NaOCN → ClSO2NCO+NaCl
This synthesis method was published in the Journal of the American Chemical Society, marking the official use of CSI as a usable synthetic reagent.
In 1955, scientists confirmed the planar triangular structure of CSI through infrared spectroscopy (IR) and X-ray diffraction analysis, in which the S=O bond has strong polarity and is suitable as an electrophilic reagent; The N=C=O group retains the high reactivity of typical isocyanates.
Early research found that CSI can react violently with water to produce chlorosulfonylamide acid (ClSO ₂ NHCOOH), demonstrating its extremely high reactivity.
FAQ
What is Chlorosulfonyl isocyanate used for?
Chlorosulfonyl isocyanate (CSI) is a complex reagent capable of facilitating numerous synthetic transformations, including lactam/lactone formation, sulfonylation, Friedel–Crafts-type acylations, and cycloadditions.
What does isocyanate do to the human body?
Health effects of isocyanate exposure include irritation of skin and mucous membranes, chest tightness, and difficult breathing. Isocyanates include compounds classified as potential human carcinogens and known to cause cancer in animals.
How to quench chlorosulfonyl isocyanate?
Chlorosulfonyl isocyanate (0.02 mL, 0.195 mmol) was added dropwise and the reaction mixture was stirred at rt for 2 h and then quenched with ice water. The ice was allowed to melt, and aqueous layer was extracted with Et2O (3 × 25 mL).
Are isocyanates cancerous?
In addition to immune sensitisation, chronic exposure to Isocyanates may cause liver and kidney disease, chronic lung damage and cancer. Isocyanates listed as suspected of causing cancer include: 4,4'-Methylene diphenyl diisocyanate.
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