Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 4-bromobenzenesulfonyl chloride cas 98-58-8 in China. Welcome to wholesale bulk high quality 4-bromobenzenesulfonyl chloride cas 98-58-8 for sale here from our factory. Good service and reasonable price are available.
4-Bromobenzenesulfonyl chloride is an organic compound, CAS 98-58-8, with the chemical formula C6H4BrCLO2S. It is a white to light yellow solid. It has a certain solubility in common solvents such as chlorinated hydrocarbons, alcohols, and ethers. It can be used for sulfonation reactions of aromatic compounds to prepare organic compounds containing sulfonic groups. Usually, this compound can serve as a sulfonation reagent for various aromatic groups, such as p-toluene, styrene, etc. It is a useful fluorescent dye precursor that can be used to synthesize fluorescent labeled biological macromolecules or organic small molecules. It can also be used to prepare heterocyclic compounds, such as organic compounds containing piperidine rings. It can also be used as a nucleophilic reagent to introduce some chemical groups, such as substituents or hydroxyl groups, onto the benzene ring.
|
|
|
|
Chemical Formula |
C6H4BrClO2S |
|
Exact Mass |
254 |
|
Molecular Weight |
256 |
|
m/z |
254 (100.0%), 256 (97.3%), 256 (32.0%), 258 (31.1%), 255 (6.5%), 257 (6.3%), 256 (4.5%), 258 (4.4%), 257 (2.1%), 259 (2.0%), 258 (1.4%), 260 (1.4%) |
|
Elemental Analysis |
C, 28.20; H, 1.58; Br, 31.27; Cl, 13.87; O, 12.52; S, 12.55 |
Physical and Chemical Properties
► Molecular Structure and Formula
It has the molecular formula C₆H₄BrClO₂S. Its structure consists of a benzene ring substituted with a bromine atom at the para position (4-position) and a sulfonyl chloride group (-SO₂Cl) attached to the ring. The sulfonyl chloride functional group is highly reactive, making this compound a valuable intermediate in organic synthesis.
► Physical State and Appearance
Under standard conditions, 4-bromobenzenesulfonyl chloride typically appears as a white to light yellow crystalline solid. The compound's appearance may vary slightly depending on its purity and storage conditions. It is odorless, which is advantageous for laboratory handling as it reduces the risk of inhalation exposure.
► Melting and Boiling Points
The melting point of 4-bromobenzenesulfonyl chloride ranges from 73°C to 77°C, with some sources reporting values as precise as 75.00–76.00°C. Its boiling point is approximately 152°C to 154°C at a pressure of 26 mmHg, indicating that it sublimates or decomposes at higher temperatures under normal atmospheric pressure. This thermal instability necessitates careful handling during heating processes.
► Solubility
It is soluble in a variety of organic solvents, including tetrahydrofuran (THF), petroleum ether, 1,4-dioxane, dichloromethane, and chloroform. However, it is insoluble in water, which is a common characteristic of sulfonyl chloride compounds. This insolubility in water is crucial for its use in anhydrous reactions, where water could interfere with the reaction mechanism.
► Sensitivity and Stability
The compound is moisture-sensitive, meaning it can react with water to form hydrogen chloride and other byproducts. This reactivity underscores the importance of storing 4-bromobenzenesulfonyl chloride in a dry, airtight container away from moisture sources. Under normal temperatures and pressures, the compound is stable but should be protected from dust generation, excess heat, and strong oxidants to prevent decomposition.
Application
► Organic Synthesis
It is a versatile reagent in organic synthesis, particularly in the preparation of sulfonamides and other sulfonyl derivatives. Its reactivity as an electrophile makes it an ideal candidate for nucleophilic substitution reactions, where it can react with amines, alcohols, or thiols to form sulfonamides, sulfonate esters, or sulfonyl thioethers, respectively.
► Synthesis of Sulfonamides
Sulfonamides are a class of compounds with diverse biological activities, including antibacterial, antifungal, and anti-inflammatory properties. It can be used to synthesize sulfonamides by reacting with primary or secondary amines. The reaction proceeds via nucleophilic attack of the amine on the sulfonyl chloride group, followed by elimination of hydrogen chloride to form the sulfonamide product.
► Protection of Amines
In addition to its role in sulfonamide synthesis, it can also be used to protect amines during multi-step synthetic processes. By converting the amine into a sulfonamide derivative, the reactive amino group is temporarily masked, preventing unwanted side reactions. After the desired transformations are complete, the sulfonamide group can be removed under specific conditions to regenerate the free amine.
► Nucleotide Synthesis
It has been employed as an activating agent in the synthesis of oligodeoxyribo- and oligoribonucleotides in solution. The sulfonyl chloride group can react with the hydroxyl groups on the nucleotide sugars, forming sulfonate esters that enhance the reactivity of the nucleotides during coupling reactions. This approach has been used to synthesize oligonucleotides with improved yields and purity compared to traditional methods.
► Other Applications
Beyond its use in organic synthesis and nucleotide chemistry, it has potential applications in material science, polymer chemistry, and agrochemical research. Its ability to form covalent bonds with various functional groups makes it a valuable tool for modifying the properties of polymers, surfaces, or small molecules.
A common method for synthesizing 4-Bromobenzenesulfonyl chloride is obtained by reacting p-bromobenzene with sulfonyl chloride. The following are the specific steps:
Chemical equation:
Reaction 1: Substitution reaction between p-bromobenzene and sulfonyl chloride
C6H5Br+SO2Cl2 → C6H5SO2Cl+HBr
Reaction 2: Neutralization reaction between unreacted sulfonyl chloride and sodium sulfide
C6H5SO2Cl+Na2S → C6H5SO2Na+NaCl+S
► Experimental preparation:
-4-bromobenzene: As the substrate of the reaction, it provides bromine atoms.
-Sulfonyl chloride: used for substitution reaction with p-bromobenzene to produce 4-Bromobenzene sulfonyl chloride.
-Anhydrous dichloromethane: serves as a solvent and provides a reaction medium.
-Sodium sulfide: used to neutralize unreacted sulfonyl chloride.
-Sulfuric acid: used to regulate reaction conditions.
-Ice and ice salt mixture: used to maintain the low temperature of the reaction system.
► Reaction steps:
a. In a dry reaction flask, add 4-bromobenzene and anhydrous dichloromethane while maintaining low temperature.
b. Slowly add sulfonyl chloride while stirring the reaction mixture.
c. Control the temperature to continue to maintain low temperature and maintain stirring during the reaction process. This reaction should be carried out at a lower temperature to control the generation of side reactions.
d. After the reaction is completed, transfer the reaction mixture to a saturated sodium chloride solution containing sodium sulfide to neutralize the unreacted sulfonyl chloride.
e. Separate the organic phase and wash with salt water.
f. Absorb the solvent to obtain 4-Bromobenzenesulfonyl chloride.
Safety Precautions
► Hazard Identification
It is a corrosive and irritating compound that can cause severe skin, eye, and respiratory tract irritation upon contact or inhalation. The compound's reactivity with water and moisture further increases the risk of hydrogen chloride gas generation, which can be harmful if inhaled.
► Health Hazards
1) Skin Contact: May cause severe burns, redness, and blistering. Prolonged or repeated exposure can lead to dermatitis or other skin disorders.
2) Eye Contact: Can cause serious eye damage, including corneal opacity, conjunctivitis, and blindness if not promptly treated.
3) Inhalation: Inhalation of vapors or dust can irritate the respiratory tract, causing coughing, shortness of breath, and chest pain. Prolonged exposure may lead to pulmonary edema or other respiratory disorders.
4) Ingestion: Although ingestion is unlikely due to the compound's solid state and handling precautions, swallowing can cause severe gastrointestinal irritation, nausea, vomiting, and abdominal pain.
► Safety Precautions
To minimize the risks associated with handling 4-bromobenzenesulfonyl chloride, the following safety precautions should be observed:
1) Personal Protective Equipment (PPE): Wear chemical-resistant gloves, safety goggles, and a lab coat or protective clothing to prevent skin and eye contact. A respirator with appropriate filters may be necessary when working with large quantities or in poorly ventilated areas.
2) Ventilation: Perform all operations in a well-ventilated area or fume hood to prevent the accumulation of vapors or dust.
3) Storage: Store the compound in a cool, dry place away from moisture, heat, and incompatible materials such as oxidizing agents and strong bases.
4) Handling: Avoid dust generation and spillage. Use a spatula or other suitable tools to transfer the solid compound, and clean up any spills immediately using appropriate absorbent materials and disposal procedures.
5) Emergency Procedures: In case of contact with skin or eyes, rinse immediately with plenty of water for at least 15 minutes and seek medical attention. If inhaled, move the affected person to fresh air and provide artificial respiration if necessary.
► Environmental Precautions
It should not be discharged into the environment, as it may be harmful to aquatic life and soil organisms. Dispose of the compound and its contaminated materials in accordance with local, state, and federal regulations for hazardous waste disposal.
It is a valuable organic compound with diverse applications in organic synthesis, nucleotide chemistry, and other fields. Its unique chemical reactivity and physical properties make it an ideal reagent for various synthetic processes. However, the compound's corrosive and irritating nature necessitates careful handling and adherence to safety precautions to prevent harm to human health and the environment. By understanding the properties, synthesis methods, applications, and safety considerations of 4-bromobenzenesulfonyl chloride, researchers and chemists can harness its potential while minimizing the associated risks.
Hot Tags: 4-bromobenzenesulfonyl chloride cas 98-58-8, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 3 Phenyltoluene, Synthetic Chemical, 3 Nitrobenzaldehyde 99 , 3 Nitrobenzonitrile, squaric acid treatment, BENZENE D6