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4,4'-Diaminodiphenylsulfone, with the chemical formula C12H12N2O2S, consists of two benzene rings and one sulfone group. The sulfone group is connected to two benzene rings through sulfur atoms. This molecule has a rigid planar structure and therefore has a certain degree of spatial stability. It is a white crystalline solid that appears in powder form at room temperature. Its melting point is about 168-172 ℃, and its boiling point is about 350 ℃. Its density is approximately 1.42 g/cm ³, Good solubility, soluble in many organic solvents such as ethanol, chloroform, and dimethyl sulfoxide, but with low solubility in water. As an important monomer for synthesizing polymers, it can be used to prepare various high-performance polymer materials, such as polyamide, polyester, and polyimide. These polymers have been widely used in industry and have excellent mechanical properties, high temperature resistance, insulation, and self-lubrication properties. They are widely used in engineering plastics, fiber reinforced materials, coatings, and other fields.
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Chemical Formula |
C12H12N2O2S |
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Exact Mass |
248 |
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Molecular Weight |
248 |
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m/z |
248 (100.0%), 249 (13.0%), 250 (4.5%) |
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Elemental Analysis |
C, 58.05; H, 4.87; N, 11.28; O, 12.89; S, 12.91 |
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4,4'-diaminodiphenylsulfone has a wide range of applications in polymer synthesis and can be used as an important monomer for synthesizing various polymers.
It can be used as one of the monomers to react with dicarboxylic acids to synthesize polyamide. Polyamide is a polymer material with excellent mechanical properties, wear resistance, high temperature resistance, and corrosion resistance. It is widely used in engineering plastics, fiber reinforced materials, wear-resistant materials, and other fields.
When synthesizing polyamide, 4,4 '- Diaminodiphenylsulfone is mixed with other dicarboxylic acids (such as adipic acid, sebacic acid, etc.) in a certain proportion, heated to a certain temperature, and the reaction generates polyamide. The molecular weight and performance of polymers can be adjusted by controlling reaction conditions and monomer ratio.
2. Synthetic polyester:
It can be used as one of the monomers to react with diols to synthesize polyester. Polyester is a polymer material with excellent mechanical properties, high temperature resistance, and weather resistance. It is widely used in packaging materials, fiber reinforced materials, coatings, and other fields.
When synthesizing polyester, it is mixed with other binary alcohols (such as ethylene glycol, propylene glycol, etc.) in a certain proportion, heated to a certain temperature, and reacted to generate polyester. The molecular weight and performance of polymers can be adjusted by controlling reaction conditions and monomer ratio.
It can be used as one of the monomers to react with binary acyl chloride to synthesize polyimide. Polyimide is a polymer material with excellent mechanical properties, high temperature resistance, insulation, and self-lubricating properties. It is widely used in fields such as engineering plastics, insulation materials, and lubricating materials.
When synthesizing polyimide, 4,4 '- Diaminodiphenylsulfone is mixed with other binary acyl chlorides (such as phthalic anhydride, para phthaloyl chloride, etc.) in a certain proportion, heated to a certain temperature, and the reaction generates polyimide. The molecular weight and performance of polymers can be adjusted by controlling reaction conditions and monomer ratio.
4,4'-Diaminodiphenylsulfone, also known as diaminodiphenyl sulfone, is a synthetic drug with antibacterial, anti-inflammatory, and immunomodulatory effects. Its chemical structure is similar to sulfonamide drugs, and it exerts antibacterial effects by interfering with bacterial folate metabolism. Since it was introduced into clinical practice in the 1940s, aminobenzene has occupied the core position in the treatment of leprosy, and has gradually expanded to skin diseases, infectious diseases, autoimmune diseases and other fields.
1. Mechanism of leprosy treatment
Aminopheniramine is the preferred drug for treating Hansen's disease, especially for the treatment of multibacterial leprosy (MB). Its mechanism of action is:
Inhibition of folate metabolism: Aminobenzoic acid competes with para aminobenzoic acid (PABA) for dihydrofolate synthase, blocking dihydrofolate synthesis and subsequently inhibiting bacterial DNA and protein synthesis.
Dual action mode: Low dose inhibits bacteria, high dose (≥ 100mg/day) can show bactericidal effect, but it needs to be combined with other drugs (such as rifampicin, clofazimine) to prevent drug resistance.
2. Clinical application plan
Combination chemotherapy (MDT): The standard regimen recommended by the World Health Organization (WHO) for multiple bacterial leprosy is amoxicillin (100mg/day) combined with rifampicin (600mg/month) and clofazimine (300mg/month), lasting for 12 months; For low bacterial leprosy (PB), amoxicillin (100mg/day) combined with rifampicin (600mg/month) is used for 6 months.
Efficacy and treatment course: Aminopheniramine can quickly relieve skin damage (such as erythema and nodules) and neurological symptoms (such as numbness and pain), but long-term medication is needed to eliminate residual bacterial communities. Research shows that standardized treatment can reduce the recurrence rate of leprosy to below 0.02%.
3. Adverse reaction management
Hematotoxicity: About 20% of patients may develop hemolytic anemia (especially G6PD deficiency), and regular monitoring of blood routine is necessary.
Skin reactions: including rash, Drug Hypersensitivity Reaction Syndrome (DRESS), severe cases require discontinuation of medication and administration of corticosteroids.
Hepatotoxicity: Long term use may cause elevated transaminase levels. It is recommended to test liver function every 3 months.
Skin disease treatment: wide coverage from inflammation to autoimmune diseases
1. Dermatitis Herpetiformis
Mechanism of action: Aminopheniramine reduces skin blisters and itching by inhibiting neutrophil chemotaxis and 5-lipoxygenase activity.
Medication plan: The initial dose is 50-100mg/day, gradually increasing to 200-300mg/day, and decreasing to the minimum maintenance dose (usually 50-100mg/day) after symptom control.
Combination therapy: Gluten free diet (GFD) is required to reduce exposure to intestinal antigens, and some patients may discontinue the use of paracetamol.
2. Other inflammatory skin diseases
Neutrophil skin diseases, such as pyoderma gangrenosum and Sweet syndrome, can be treated with paracetamol to inhibit neutrophil infiltration, alleviate ulcers and pain.
Vasculitic diseases, such as skin allergic vasculitis and nodular erythema, reduce erythema and swelling through anti-inflammatory effects.
Psoriasis and Acne: It has certain therapeutic effects on pustular psoriasis and acne vulgaris, but caution should be taken against drug side effects.
3. Autoimmune skin diseases
Discoid lupus erythematosus (DLE): Aminopheniramine can alleviate skin erythema and scales, but caution should be exercised when using systemic lupus erythematosus (SLE) as it may induce hemolysis.
Bullous skin diseases, such as pemphigus and pemphigoid, reduce the formation of blisters by inhibiting the inflammatory response mediated by autoantibodies.
Infectious diseases: from parasites to opportunistic infections
1. Pneumocystis carinii pneumonia (PCP)
Mechanism of action: 4,4'-Diaminodiphenylsulfone inhibits the folate metabolism of Pneumocystis carinii and blocks its proliferation.
Medication plan: Used in combination with trimethoprim (TMP) (TMP 15mg/kg/day+paracetamol 50mg/kg/day, divided into 3 oral doses), for a course of 14-21 days.
Applicable population: high-risk groups such as HIV infected individuals (CD4+T cell count<200/μ L) or organ transplant recipients.
2. Malaria prevention and treatment
Drug resistant malaria: Aminopheniramine combined with ethambutol is used to prevent chloroquine resistant malaria (such as Plasmodium vivax), with a dose of 100 mg/week of aminopheniramine and 12.5 mg/week of ethambutol.
Triple therapy: In areas with high malaria prevalence, chloroquine (300mg/week) can be combined to enhance the preventive effect.
1. Recurrent Polychondritis (RP)
Mechanism of action: Aminopheniramine alleviates ear, nose, and joint pain by inhibiting immune-mediated cartilage destruction.
Medication plan: The initial dose is 100mg/day, adjusted to 200mg/day according to the condition, often used in combination with glucocorticoids.
2. Granuloma Annuule
Clinical effect: For generalized or refractory annular granulomas, paracetamol can promote the regression of skin lesions, but long-term medication (6-12 months) is required.
3. Critical care supportive treatment
Burn patients: Aminobenzene can reduce the risk of Pseudomonas aeruginosa infection in burn wounds, but caution should be taken against hemolytic reactions.
Actinomycosis: For skin infections caused by actinomycetes, paracetamol can be used as an adjuvant treatment drug.
Synthetic diphenylsulfone: the molten 4 4'-diaminodiphenylsulfone is pumped into the pipeline reactor through a high-pressure pump at a flow rate of 140 g/h, while the mixture of 25% ammonia and cuprous chloride is also pumped into the pipeline reactor through a high-pressure pump at a flow rate of 800 g/h (of which the flow rate of cuprous chloride is 5.6 g/h), and the continuous ammonolysis reaction is carried out at a pressure of 14 Mpa and a temperature of 220 ℃, The residence time of reaction material in high-pressure pipeline is 20 minutes; After decompression and discharge through the pressure reducing valve, the product is analyzed by liquid chromatography, and the ammonolysis product contains 4,4 '- dichlorodiphenyl sulfone 0.1%. The discharge is sent to the recovery unit, the excess ammonia is distilled, and the crude 4,4' - diaminodiphenyl sulfone is separated; The crude product is dissolved in hydrochloric acid with a mass fraction of 10% at 30 ℃, decolored with activated carbon, filtered, cooled to below 10 ℃, adjusted the pH value to 2~2.5 with a mass fraction of 10% sodium carbonate solution, centrifuged, washed to neutral, and dried to obtain a finished product of 4,4 '- diaminodiphenyl sulfone with a purity of 99.5% (liquid chromatography analysis), with a total yield of 97.1% (calculated by 4,4' - dichlorodiphenyl sulfone).
Pharmacological action:
4,4'-Diaminodiphenylsulfone is a sulfone antibacterial agent, which has strong antibacterial effect on leprosy bacilli, and shows bactericidal effect in large doses. Its mechanism of action is similar to that of sulfonamide drugs. It acts on the dihydrofolate synthetase of bacteria and interferes with the synthesis of folate. The antibacterial spectrum of both of them is similar, and both of them are antagonized by aminobenzoic acid. This product can also be used as dihydrofolate reductase inhibitor. In addition, this product has immunosuppressive effect, which may be related to the inhibition of herpetiform dermatitis. If it is used alone for a long time, leprosy bacilli is prone to develop drug resistance to this product.
Pharmacokinetics:
This product is absorbed rapidly and completely after oral administration. The protein binding rate is 50%~90%. After absorption, it is widely distributed in the tissues and body fluids of the whole body. The concentration of liver and kidney is the highest. The concentration of damaged skin is 10 times higher than that of normal skin. This product is metabolized by N-acetyltransferase in the liver. The patients can be divided into the slow acetylation type and the fast acetylation type of dapsone. The former has a higher peak concentration of blood drug after taking medicine, which is prone to produce adverse reactions, especially adverse reactions in the blood system, but the clinical efficacy has not increased. Patients with fast acetylation may need to adjust the dose when taking medicine. The product can be measured in the blood a few minutes after oral administration. The peak time is 2 to 6 hours, sometimes 4 to 8 hours. The product has hepatobiliary circulation, so the excretion is slow, and the elimination half-life is 10 to 50 hours (average 28 hours). After stopping the drug, the product can still exist in the blood for several weeks. About 70%~85% of the dose is excreted from the urine as prototype and metabolites, and a small amount is excreted through feces, sweat, saliva, sputum and milk.
Aminobenzenesulfone, as a sulfone antibacterial drug, is mainly used to treat various types of leprosy caused by Mycobacterium leprae. It is also used for the treatment of various skin diseases, such as herpetic dermatitis and pustular dermatitis. However, any medication used to treat a disease may also be accompanied by certain toxic reactions. The toxicity of dapsone can be elaborated in detail from the following aspects:
Common adverse reactions
Gastrointestinal irritation:
Some patients may experience gastrointestinal irritation symptoms such as nausea, upper abdominal discomfort, and decreased appetite during the initial use of dapsone. These reactions are generally mild and often occur in the early stages of treatment. As the medication time prolongs, the symptoms usually gradually alleviate or disappear.
Neurological symptoms:
Some patients may also experience neurological symptoms such as headache, dizziness, insomnia, and weakness. These reactions are also mostly temporary and can disappear after discontinuing the medication.
Toxic reactions
Hemolytic anemia:
Aminobenzenesulfone can cause hemolytic anemia, especially when the dosage is high or the patient has a deficiency of glucose-6-phosphate dehydrogenase (G-6-PD), which is more likely to occur. The incidence of hemolytic anemia is dose-dependent, and it is more likely to occur when the daily dose exceeds 200mg. Mild anemia generally does not require discontinuation of medication and can be treated with iron supplements and complex vitamin B; Severe cases should stop taking medication and receive corresponding treatment.
Hyperhemoglobinopathy:
A single dose of dapsone can convert hemoglobin into methemoglobin, causing symptoms such as tissue hypoxia and cyanosis. This reaction is quite serious, and if left untreated, it can lead to toxic hepatitis, nephritis, neurological and psychiatric damage, and even endanger life.
Exfoliation dermatitis:
Aminobenzenesulfone can cause drug rash, and in severe cases, it can manifest as exfoliative dermatitis, accompanied by symptoms such as fever, lymphadenopathy, liver and kidney dysfunction, and increased monocytes. This is called "Aminobenzenesulfone syndrome". Peeling dermatitis is a serious skin reaction that requires immediate discontinuation of medication and appropriate treatment.
Other toxic reactions
Liver damage:
When the dosage is too high, dapsone can cause acute liver damage. Therefore, liver function should be closely monitored during medication, and any abnormalities should be promptly stopped and treated.
Peripheral neuritis:
Although the incidence is low, some patients may experience symptoms of peripheral neuropathy such as limb numbness and sensory abnormalities after using dapsone. This reaction is generally mild and mostly temporary.
Taboos and Precautions
Contraindications:
Aminobenzenesulfone is contraindicated for individuals allergic to sulfonyl drugs; Use with caution in patients with severe anemia, G-6-PD deficiency, liver dysfunction, degenerative hemoglobin reductase deficiency, and renal dysfunction.
Cross allergy:
Patients who are allergic to one sulfone drug may also be allergic to other sulfone drugs; Patients who are allergic to furosemide diuretics, sulfonylureas, carbonic anhydrase inhibitors, or other sulfonamide drugs may also be sensitive to sulfamethoxazole.
Drug interactions:
Aminobenzenesulfone should not be used in combination with drugs that can cause bone marrow suppression, as it can exacerbate the degree of leukopenia and thrombocytopenia; When combined with trimethoprim, the blood concentrations of both can increase, which may exacerbate adverse reactions; Deoxyinosine can reduce the absorption of dapsone, and when they must be used together, there should be at least a 2-hour interval.
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