4,4'-Diaminodiphenylsulfone
- CAS No.
- 80-08-0
- Chemical Name:
- 4,4'-Diaminodiphenylsulfone
- Synonyms
- DDS;DAPSONE;DADPS;DAPSON;Acedapsone;AVLOSULFON;4-AMINOPHENYL SULFONE;4,4'-SULFONYLDIANILINE;4-Aminophen;DIAMINODIPHENYLSULPHONE
- CBNumber:
- CB0152851
- Molecular Formula:
- C12H12N2O2S
- Molecular Weight:
- 248.3
- MOL File:
- 80-08-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/30 21:22:42
| Melting point | 175-177 °C(lit.) |
|---|---|
| Boiling point | 511.7±35.0 °C(Predicted) |
| Density | 1.2701 (rough estimate) |
| vapor pressure | 0.004Pa at 25℃ |
| refractive index | 1.5950 (estimate) |
| storage temp. | 2-8°C |
| solubility | 0.38g/l |
| form | Crystalline Powder |
| pka | pKb 13.0(at 25℃) |
| color | White to beige |
| PH | 5.5-7.5 (H2O, 20℃)(saturated aqueous solution) |
| Water Solubility | <0.1 g/100 mL at 20 ºC |
| Merck | 14,2822 |
| BRN | 788055 |
| BCS Class | 4,2 |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChIKey | MQJKPEGWNLWLTK-UHFFFAOYSA-N |
| LogP | 0.97 at 25℃ |
| CAS DataBase Reference | 80-08-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Dapsone(80-08-0) |
| IARC | 3 (Vol. 24, Sup 7) 1987 |
| EPA Substance Registry System | Dapsone (80-08-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS07,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H370-H373-H411 | |||||||||
| Precautionary statements | P260-P264-P270-P273-P301+P312-P308+P311 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22 | |||||||||
| Safety Statements | 22 | |||||||||
| RIDADR | 3249 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | BY8925000 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29051620 | |||||||||
| HS Code | 29309070 | |||||||||
| Toxicity | LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 4000 mg/kg | |||||||||
| NFPA 704 |
|
4,4'-Diaminodiphenylsulfone price More Price(10)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A74807 | 4-Aminophenyl sulfone 97% | 80-08-0 | 100G | ₹5390.85 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1464 | Dapsone Pharmaceutical Secondary Standard; Certified Reference Material | 80-08-0 | 1G | ₹9103.83 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A74807 | 4-Aminophenyl sulfone 97% | 80-08-0 | 500G | ₹12535.35 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.21073 | 4,4′-Diaminodiphenyl sulfone for synthesis | 80-08-0 | 5G | ₹1980 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.21073 | 4,4′-Diaminodiphenyl sulfone for synthesis | 80-08-0 | 250G | ₹6710 | 2022-06-14 | Buy |
4,4'-Diaminodiphenylsulfone Chemical Properties,Uses,Production
Chemical Properties
Off -White Crystalline Solid
Uses
4,4'-diaminodiphenylsulfone be used for preparation polyimide and epoxy resin material.
Indications
Although dapsone (Avlosulfon) is most often used as an antimicrobial agent, it has important antiinflammatory properties in many noninfectious skin diseases. The mechanism of action of dapsone in skin disease is not clear.Most of the cutaneous diseases for which it is effective manifest inflammation and are characterized by an infiltration of neutrophils; the drug’s antiinflammatory effect may arise from its inhibition of intracellular neutrophil reactions mediated by myeloperoxidase and hydrogen peroxide or from its scavenging of reactive oxygen species, which inhibits inflammation.
Definition
ChEBI: A sulfone that is diphenylsulfone in which the hydrogen atom at the 4 position of each of the phenyl groups is substituted by an amino group. It is active against a wide range of bacteria, but is mainly employed for its actions against Mycobacteriu leprae, being used as part of multidrug regimens in the treatment of all forms of leprosy.
Antimicrobial activity
Dapsone is active against many bacteria and some protozoa. Fully susceptible strains of M. leprae are inhibited by a little as 0.003 mg/L. It is predominantly bacteristatic. Resistance is associated with mutations in the folP1 gene involved in the synthesis of para-aminobenzoic acid.
Acquired resistance
Resistance to high levels is acquired by several sequential mutations. As a result of prolonged use of dapsone monotherapy, acquired resistance emerged in patients with multibacillary leprosy in many countries. Initial resistance also occurs in patients with both paucibacillary and multibacillary leprosy. Thus, leprosy should always be treated with multidrug regimens. Resistance of M. leprae to dapsone (and other anti-leprosy drugs) may now be determined by use of DNA microarrays.
General Description
Odorless white or creamy white crystalline powder. Slightly bitter taste.
Air & Water Reactions
Sensitive to oxidation and light. Insoluble in water.
Reactivity Profile
4,4'-Diaminodiphenylsulfone can neutralize acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Incompatible with strong oxidizing agents. Also incompatible with epoxy resins under uncontrolled conditions .
Fire Hazard
4,4'-Diaminodiphenylsulfone is probably combustible.
Pharmaceutical Applications
The most effective of a number of sulfonamide derivatives to be tested against leprosy. The dry powder is very stable. It is only slightly soluble in water.
Pharmacokinetics
Oral absorption: >90%
Cmax 100 mg oral: c. 2 mg/L after 3–6 h
Plasma half-life: 10–50 h
Plasma protein binding: c. 50%
It is slowly but almost completely absorbed from the intestine
and widely distributed in the tissues, but selectively
retained in skin, muscle, kidneys and liver. It is metabolized
by N-oxidation and also by acetylation, which is subject to the
same genetic polymorphism as isoniazid. The elimination
half-life is consequently very variable, but on standard
therapy the trough levels are always well in excess of inhibitory
concentrations. It is mostly excreted in the urine: in the
unchanged form (20%), as N-oxidation products (30%) and
as a range of other metabolites.
Clinical Use
Leprosy (multidrug regimens)
Prophylaxis of malaria, treatment of chloroquine-resistant malaria (in
combination with pyrimethamine)
Prophylaxis of toxoplasmosis (in combination with pyrimethamine)
Prophylaxis (monotherapy) and treatment (in combination with
trimethoprim) of Pneumocystis jirovecii pneumonia
Dermatitis herpetiformis and related skin disorders
Side effects
Although usually well tolerated at standard doses, gastrointestinal
upsets, anorexia, headaches, dizziness and insomnia may
occur. Less frequent reactions include skin rashes, exfoliative
dermatitis, photosensitivity, peripheral neuropathy (usually
in non-leprosy patients), tinnitus, blurred vision, psychoses,
hepatitis, nephrotic syndrome, systemic lupus erythematosus
and generalized lymphadenopathy.
The term ‘dapsone syndrome’ is applied to a skin rash and
fever occurring 2–8 weeks after starting therapy and sometimes
accompanied by lymphadenopathy, hepatomegaly,
jaundice and/or mononucleosis.
Blood disorders include anemia, methemoglobinemia,
sulfhemoglobinemia, hemolysis (notably in patients with
glucose-
6-phosphate dehydrogenase deficiency), mononucleosis,
leukopenia and, rarely, agranulocytosis. Severe anemia
should be treated before patients receive dapsone.
The incidence of adverse reactions declined in the 1960s
but reappeared around 1982 when multidrug therapy was
introduced, and may represent an unexplained interaction
with rifampicin.
Safety Profile
Poison by ingestion, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: agranulocytosis, change in tubules and other kidney changes, cyanosis, effect on joints, hemolysis with or without anemia, jaundice, methemoglobinemiacarboxyhemoglobinemia, retinal changes, somnolence. Experimental reproductive effects. Can cause hepatitis, dermatitis, and neuritis. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. Used in leprosy treatment and veterinary medicine. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also SULFONATES.
4,4'-Diaminodiphenylsulfone Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| ANJI BIOSCIENCES | +91-9000100077 +91-9000100077 | Hyderabad, India | 430 | 58 | Inquiry |
| AVD pharmaceuticals Pvt Ltd | +919860835260 | Pune, India | 102 | 58 | Inquiry |
| Rsum Industries Pvt. Ltd. | +91-91062685255 +91-91062685255 | New Delhi, India | 29 | 58 | Inquiry |
| Nuray Chemicals Pvt Ltd | +91-4066616700 +91-8220444745 | Tamil Nadu, India | 49 | 58 | Inquiry |
| ZCL Chemicals Ltd | +91-2261539999 +91-2261539999 | Maharashtra, India | 53 | 58 | Inquiry |
| Aruvi Labs | +91-8056181939 +91-8056181939 | Tamil Nadu, India | 149 | 58 | Inquiry |
| SMS Lifesciences India Ltd (MAHI Drugs Pvt Ltd) | +91-40-66288888 +91-8374455507 | Telangana, India | 23 | 58 | Inquiry |
| BanChem Group | +91-9321395999 +91-9769361999 | Maharashtra, India | 26 | 58 | Inquiry |
| Medilux Laboratories Pvt Ltd | +91-7292409991 +91-9819666688 | Madhya Pradesh, India | 102 | 58 | Inquiry |
| AKASH PHARMA EXPORTS | +91-9388123451 +91-9846039283 | Kerela, India | 470 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| ANJI BIOSCIENCES | 58 |
| AVD pharmaceuticals Pvt Ltd | 58 |
| Rsum Industries Pvt. Ltd. | 58 |
| Nuray Chemicals Pvt Ltd | 58 |
| ZCL Chemicals Ltd | 58 |
| Aruvi Labs | 58 |
| SMS Lifesciences India Ltd (MAHI Drugs Pvt Ltd) | 58 |
| BanChem Group | 58 |
| Medilux Laboratories Pvt Ltd | 58 |
| AKASH PHARMA EXPORTS | 58 |
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