4,4'-Diaminodiphenylsulfone

Base Information

• Chemical Name: 4,4'-Diaminodiphenylsulfone
• CAS No.: 80-08-0
• Deprecated CAS: 1246638-15-2
• Molecular Formula: C12H12N2O2S
• Molecular Weight: 248.305
• Hs Code.: 29309070
• European Community (EC) Number: 201-248-4
• NSC Number: 756716,6091
• UNII: 8W5C518302
• DSSTox Substance ID: DTXSID4020371
• Nikkaji Number: J4.247A
• Wikipedia: Dapsone
• Wikidata: Q422226
• NCI Thesaurus Code: C415
• RXCUI: 3108
• Pharos Ligand ID: YS6TQYFAMGM5
• Metabolomics Workbench ID: 42651
• ChEMBL ID: CHEMBL1043
• Mol file: 80-08-0.mol

Synonyms:Aniline,4,4'-sulfonyldi- (7CI,8CI);1,1'-Sulfonylbis[4-aminobenzene];Benzenamine,4,4'-sulfonylbis-;4,4'-Dapsone;4,4'-Diaminodiphenyl sulfone;4,4'-Sulfonylbisbenzamine;4,4'-Sulfonyldianiline;4,4'-Sulphonyldianiline;Aczone;Atrisone;Avlosulfon;Avlosulphone;Croysulfone;Croysulphone;Dapson;Di(p-aminophenyl) sulfone;Diaphenylsulfon;Diaphenylsulfone;Diphone;Eporal;Hardener HT 976;Lapox K 10;Novophone;Servidapson;Sulfona;Sulfona-Mae;Sulphadione;Sumicure S;p-Aminophenyl sulfone;

Chemical Property of 4,4'-Diaminodiphenylsulfone

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 0.004Pa at 25℃
• Melting Point: 175-177 °C(lit.)
• Refractive Index: 1.5950 (estimate)
• Boiling Point: 511.7 °C at 760 mmHg
• PKA: pKb 13.0(at 25℃)
• Flash Point: 263.2 °C
• PSA: 94.56000
• Density: 1.361 g/cm³
• LogP: 3.92700
• Storage Temp.: -20°C Freezer
• Solubility.: 0.38g/l
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 248.06194880
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

Dapsone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Curing Agents (Aromatic)
• Drug Classes: Antiinfective Agents
• Canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
• Recent ClinicalTrials: A Randomized Multicenter Study for Isolated Skin Vasculitis
• Recent EU Clinical Trials: A phase II trial assessing dapsone topical gel in the prevention and treatment of erlotinib associated rash
• Recent NIPH Clinical Trials: A Randomized Multicenter Study for Isolated Skin Vasculitis
• Uses: An antibacterial used in the treatment of dermatitis herpetiformis antibacterial, leprostatic, dermatitis herpetiformis suppressant Hardening agent in the curing of epoxy resins.
• 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. Although dapsone (Avlosulfon) was once used in the treatment and prophylaxis of chloroquine-resistant P. falciparum malaria, the toxicities associated with its administration (e.g., agranulocytosis, methemoglobinemia, hemolytic anemia) have severely reduced its use. Occasionally dapsone has been added to the usual chloroquine therapeutic regimen for the prophylaxis of chloroquine-resistant P. falciparum malaria. It is also used in combination therapy for leprosy.
• Clinical Use: Dapsone (4,4 -sulfonylbisbenzeneamine; 4,4 -sulfonyldianiline;p,p -diaminodiphenylsulfone; or DDS [Avlosulfon])occurs as an odorless, white crystalline powder that is veryslightly soluble in water and sparingly soluble in alcohol.The pure compound is light stable, but traces of impurities,including water, make it photosensitive and thus susceptibleto discoloration in light. Although no chemical change is detectablefollowing discoloration, the drug should be protectedfrom light.Dapsone is used in the treatment of both lepromatous andtuberculoid types of leprosy. Dapsone is used widely for allforms of leprosy, often in combination with clofazimine andrifampin. Initial treatment often includes rifampin with dapsone,followed by dapsone alone. It is also used to preventthe occurrence of multibacillary leprosy when given prophylactically.Dapsone is also the drug of choice for dermatitis herpetiformisand is sometimes used with pyrimethamine for treatmentof malaria and with trimethoprim for PCP.Serious side effects can include hemolytic anemia,methemoglobinemia, and toxic hepatic effects. Hemolyticeffects can be pronounced in patients with glucose-6-phosphatedehydrogenase deficiency. During therapy, all patientsrequire frequent blood counts. Dapsone is approved for the treatment of an autoimmune blistering skin disease, dermatitis herpetiformis. This intensely pruritic eruption is characterized histologically by a dense dermal infiltration of neutrophils and subepidermal blisters. Other skin diseases in which dapsone is helpful are linear immunoglobulin A (IgA) dermatosis, subcorneal pustular dermatosis, leukocytoclastic vasculitis, and a variety of rarer eruptions in which neutrophils predominate, including some forms of cutaneous lupus erythematosus. 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
• Drug interactions: Potentially hazardous interactions with other drugsAntivirals: increased risk of ventricular arrhythmias with saquinavir - avoid.

Technology Process of 4,4'-Diaminodiphenylsulfone

There total 69 articles about 4,4'-Diaminodiphenylsulfone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-nitrophenyl sulfone (1156-50-9) → dapsone (80-08-0)

Guidance literature:

With hydrazine hydrate; nickel; In ethanol; 1,2-dichloro-ethane; at 28 ℃; for 9h; Product distribution; other catalysts, other solvents, other reaction conditions;

DOI:10.1055/s-1981-29557

Reference yield: 98.0%

4,4'-dibromodiphenyl sulfone (2050-48-8) → dapsone (80-08-0)

Guidance literature:

With copper(I) oxide; ammonium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 20h; Sealed tube;

DOI:10.1039/c4cc05964f

Reference yield: 95.0%

bis-(4-azido-phenyl)-sulfone (7300-27-8) → dapsone (80-08-0)

Guidance literature:

With methanol; sodium sulfide; for 0.0833333h;

DOI:10.1080/10426500490466544

upstream raw materials:

4,4'-sulfinyldianiline

4,4'-sulfonediphenol

4,4'-dichlorodiphenyl sulphone

4-nitrophenyl sulfone

Downstream raw materials:

4,4'-bis-(2-pyridinethiocarboxamido)-diphenylsulfone

4,4'-di(furan-2-formylimino)diphenyl sulphone

4,4'-di(thiophene-2-formylimino)diphenyl sulphone

bis-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-sulfone

Refernces

• 1、 Dodds, Amy C.,Sutherland, Andrew. "Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis". . p. 5922 - 5932. Retrieved 2021/05/04.
• 2、 -. "NEW CYCLOADDUCT PRECURSORS OF DIHALODIPHENYLSULFONES AND PREPARATIONS THEREOF". Page/Page column 21. . Retrieved 2019/02/25.