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80-08-0 Usage

Chemical Properties

Off -White Crystalline Solid

Originator

Avlosulfon,Ayerst,US,1957

Uses

Different sources of media describe the Uses of 80-08-0 differently. You can refer to the following data:
1. An antibacterial used in the treatment of dermatitis herpetiformis
2. antibacterial, leprostatic, dermatitis herpetiformis suppressant
3. Hardening agent in the curing of epoxy resins.

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.

Indications

Different sources of media describe the Indications of 80-08-0 differently. You can refer to the following data:
1. 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.
2. 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.

Manufacturing Process

p-Chloronitrobenzene is reacted with NaSO2C6H5NHCOCH3 to give as an intermediate, O2NC6H5SO2C6H5NHCOCH3 which is then reduced and deacetylated to give the product, dapsone. Alternatively, benzene and sulfuric acid react to give phenyl sulfone which is nitrated, then reduced to give dapsone.

Synthesis Reference(s)

Synthesis, p. 640, 1981 DOI: 10.1055/s-1981-29557

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

Different sources of media describe the Clinical Use of 80-08-0 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.

Synthesis

Dapsone, 4,4-diaminodiphenylsulfone (34.2.3), is synthesized from either 4-chloronitrobenzene or from the sodium salt of 4-acetamidobenzenesulfonic acid. Reacting 4-chloronitrobenzene with sodium sulfide gives 4,4-dinitrodiphenylthioester (34.2.1), and oxidation of the sulfur atom in this compound using potassium dichromate in sulfuric acid gives 4,4-dinitrodiphenylsulfone (34.2.2). Reduction of the nitro group in the resulting compound using tin dichloride in hydrochloric acid makes the desired dapsone. It has also been suggested to reduce the nitro group to an amino group, protect it with an acetyl protection, oxidize the sulfur atom to a sulfone using potassium dichromate, and then remove the protective acetyl group by hydrolysis. Another way of the synthesis of dapsone begins with 4-acetamidobenzenesulfonic acid, which is reacted with 4-chloronitrobenzene at high temperatures to give 4-acetamido-4- nitrodiphenylsulfone (34.2.4). Reducing the nitro group in this compound with tin dichloride in hydrochloric acid along with the simultaneous hydrolysis of the acetyl group under the reaction conditions gives the desired dapsone.

Drug interactions

Potentially hazardous interactions with other drugsAntivirals: increased risk of ventricular arrhythmias with saquinavir - avoid.

Metabolism

Dapsone undergoes enterohepatic recycling. Dapsone is acetylated to monoacetyldapsone, the major metabolite, and other mono and diacetyl derivatives. Acetylation shows genetic polymorphism. Hydroxylation is the other major metabolic pathway resulting in hydroxylamine dapsone, which may be responsible for dapsoneassociated methaemoglobinaemia and haemolysis. Dapsone is mainly excreted in the urine, only 20% of a dose as unchanged drug.

Check Digit Verification of cas no

The CAS Registry Mumber 80-08-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 80-08:
(4*8)+(3*0)+(2*0)+(1*8)=40
40 % 10 = 0
So 80-08-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H10O2S.C7H6N2O5/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12;1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h1-10H;2-3,10H,1H3

80-08-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D0089)  Bis(4-aminophenyl) Sulfone  >97.0%(T)

  • 80-08-0

  • 25g

  • 80.00CNY

  • Detail
  • TCI America

  • (D0089)  Bis(4-aminophenyl) Sulfone  >97.0%(T)

  • 80-08-0

  • 100g

  • 240.00CNY

  • Detail
  • TCI America

  • (D0089)  Bis(4-aminophenyl) Sulfone  >97.0%(T)

  • 80-08-0

  • 500g

  • 750.00CNY

  • Detail
  • Alfa Aesar

  • (A18976)  4,4'-Diaminodiphenyl sulfone, 98%   

  • 80-08-0

  • 100g

  • 421.0CNY

  • Detail
  • Alfa Aesar

  • (A18976)  4,4'-Diaminodiphenyl sulfone, 98%   

  • 80-08-0

  • 500g

  • 1497.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1464)  Dapsone  pharmaceutical secondary standard; traceable to USP, PhEur, BP

  • 80-08-0

  • PHR1464-1G

  • 791.15CNY

  • Detail
  • Sigma-Aldrich

  • (D0100000)  Dapsone  European Pharmacopoeia (EP) Reference Standard

  • 80-08-0

  • D0100000

  • 1,880.19CNY

  • Detail
  • USP

  • (1164008)  Dapsone  United States Pharmacopeia (USP) Reference Standard

  • 80-08-0

  • 1164008-200MG

  • 4,588.74CNY

  • Detail
  • Sigma-Aldrich

  • (46158)  Dapsone  VETRANAL, analytical standard

  • 80-08-0

  • 46158-250MG

  • 360.36CNY

  • Detail
  • Aldrich

  • (A74807)  4-Aminophenylsulfone  97%

  • 80-08-0

  • A74807-100G

  • 664.56CNY

  • Detail
  • Aldrich

  • (A74807)  4-Aminophenylsulfone  97%

  • 80-08-0

  • A74807-500G

  • 2,190.24CNY

  • Detail

80-08-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name dapsone

1.2 Other means of identification

Product number -
Other names 4,4'-Diaminodiphenylsulfone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals,Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80-08-0 SDS

80-08-0Synthetic route

4-nitrophenyl sulfone
1156-50-9

4-nitrophenyl sulfone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrazine hydrate; nickel In ethanol; 1,2-dichloro-ethane at 28℃; for 9h; Product distribution; other catalysts, other solvents, other reaction conditions;99%
With hydrazine hydrate; nickel In ethanol; 1,2-dichloro-ethane at 28℃; for 8h;98%
With methanol; nickel
4,4'-dibromodiphenyl sulfone
2050-48-8

4,4'-dibromodiphenyl sulfone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In dimethyl sulfoxide at 90℃; for 20h; Sealed tube;98%
bis-(4-azido-phenyl)-sulfone
7300-27-8

bis-(4-azido-phenyl)-sulfone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With methanol; sodium sulfide for 0.0833333h;95%
4,4'-dichlorodiphenyl sulphone
80-07-9

4,4'-dichlorodiphenyl sulphone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With ammonium chloride In ethanol for 5h; Reflux;91.9%
With ammonia; water; copper; copper(I) bromide at 200℃;
With ammonia; copper(II) sulfate; ethylene glycol at 245℃;
4-amino-4'-nitrodiphenyl sulfide
101-59-7

4-amino-4'-nitrodiphenyl sulfide

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
Stage #1: 4-amino-4'-nitrodiphenyl sulfide With hydrogen; toluene-4-sulfonic acid; palladium 10% on activated carbon In methanol; water at 50℃; under 3750.38 Torr;
Stage #2: With ammonia In water Product distribution / selectivity;
82%
Stage #1: 4-amino-4'-nitrodiphenyl sulfide With methanesulfonic acid; hydrogen; 5%-palladium/activated carbon In methanol; water at 50℃; under 3000.3 Torr; for 4h;
Stage #2: With ammonia In water at 50℃; Product distribution / selectivity;
80%
Multi-step reaction with 4 steps
1: tin; aqueous hydrochloric acid / Hydrogenation
2: acetic acid
3: potassium dichromate; aqueous sulfuric acid; acetic acid
4: aqueous hydrochloric acid
View Scheme
Multi-step reaction with 4 steps
1: sulfur; sodium sulfide nonahydrate / 130 - 135 °C / Hydrogenation
2: ethanol / 40 °C
3: sodium dichromate; aqueous sulfuric acid
4: aqueous hydrochloric acid
View Scheme
acedapsone
77-46-3

acedapsone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Heating;80%
Stage #1: acedapsone With hydrogenchloride In water for 1h; Reflux;
Stage #2: With pyrographite In water for 1h; Reflux;
65%
With hydrogenchloride
4,4'-dichlorodiphenyl sulphone
80-07-9

4,4'-dichlorodiphenyl sulphone

A

4-(4-chloro-benzenesulfonyl)-aniline
7146-68-1

4-(4-chloro-benzenesulfonyl)-aniline

B

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With para-dinitrobenzene; ammonium hydroxide In water at 250℃; for 3h; autoclave;A 20.5%
B 78%
With para-dinitrobenzene; ammonium hydroxide In water at 250℃; for 3h; Product distribution; Mechanism; various radical-ion inhibitors;A 20.5%
B 78%
With ammonium hydroxide; 1,3,5-trinitrobenzene In water at 250℃; for 3h; autoclave;A 25%
B 73.5%
With ethanol; ammonia; copper(II) sulfate at 200℃;
4,4'-thiobisaniline
139-65-1

4,4'-thiobisaniline

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 50℃; for 3h; chemoselective reaction;71%
Multi-step reaction with 3 steps
1: acetic acid
2: potassium dichromate; aqueous sulfuric acid; acetic acid
3: aqueous hydrochloric acid
View Scheme
Multi-step reaction with 3 steps
1: acetic acid
2: acetic acid / 40 °C
3: aqueous hydrochloric acid
View Scheme
4-bromo-aniline
106-40-1

4-bromo-aniline

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;58%
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;46%
4,4'-sulfinyldianiline
119-59-5

4,4'-sulfinyldianiline

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With potassium permanganate; acetic acid; acetone Reagens 4: Kupfer(II)-sulfat;
Multi-step reaction with 3 steps
1: acetic acid
2: potassium permanganate; aqueous acetic acid / bei Siedetemperatur
3: aqueous hydrochloric acid
View Scheme
4,4'-sulfonediphenol
80-09-1

4,4'-sulfonediphenol

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With diammine zinc-chloride; ammonia at 200℃;
4-(4-nitrophenylsulfonyl)aniline
1948-92-1

4-(4-nitrophenylsulfonyl)aniline

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
monoacetyldapsone
565-20-8

monoacetyldapsone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride
acetic acid-[4-(4-chloro-benzenesulfonyl)-anilide]
6630-10-0

acetic acid-[4-(4-chloro-benzenesulfonyl)-anilide]

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With ammonia; water; copper(l) chloride at 180 - 190℃;
N-[4-(4-Nitro-benzenesulfonyl)-phenyl]-acetamide
1775-37-7

N-[4-(4-Nitro-benzenesulfonyl)-phenyl]-acetamide

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal Hydrogenation;
With iron at 90 - 95℃; Hydrogenation;
With hydrogenchloride; tin(ll) chloride
4,4'-sulfonyl-di-benzoic acid diamide
14052-63-2

4,4'-sulfonyl-di-benzoic acid diamide

dapsone
80-08-0

dapsone

4-((4-bromophenyl)sulfonyl)aniline
6626-22-8

4-((4-bromophenyl)sulfonyl)aniline

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With ammonia; water; copper at 210 - 220℃;
carbon disulfide
75-15-0

carbon disulfide

methyl chlorosulfate
812-01-1

methyl chlorosulfate

Acetanilid
103-84-4

Acetanilid

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With hydrogenchloride; aluminium trichloride; zinc(II) chloride
ethanol
64-17-5

ethanol

N-furfurylidene-4-(4-nitro-benzenesulfonyl)-aniline
68997-77-3

N-furfurylidene-4-(4-nitro-benzenesulfonyl)-aniline

sodium hydrogensulfite

sodium hydrogensulfite

A

furfural
98-01-1

furfural

B

dapsone
80-08-0

dapsone

4,4'-dichlorodiphenyl sulphone
80-07-9

4,4'-dichlorodiphenyl sulphone

ammonia
7664-41-7

ammonia

copper(II) sulfate
7758-99-8

copper(II) sulfate

ethylene glycol
107-21-1

ethylene glycol

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
at 245℃;
at 245℃;
ethanol
64-17-5

ethanol

4-(4-nitro-benzenesulfonyl)-N-(3-nitro-benzyliden)-aniline
68997-76-2

4-(4-nitro-benzenesulfonyl)-N-(3-nitro-benzyliden)-aniline

sodium dithionite

sodium dithionite

dapsone
80-08-0

dapsone

ethanol
64-17-5

ethanol

4-(4-nitro-benzenesulfonyl)-N-trans-cinnamyliden-aniline

4-(4-nitro-benzenesulfonyl)-N-trans-cinnamyliden-aniline

sodium dithionite

sodium dithionite

A

3-phenyl-propenal
104-55-2

3-phenyl-propenal

B

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
beim Erwaermen tritt Zersetzung;
bis-[4-(dichlorophosphoryl-amino)-phenyl]-sulfone
856800-21-0

bis-[4-(dichlorophosphoryl-amino)-phenyl]-sulfone

aqueous sodium hydrogencarbonate

aqueous sodium hydrogencarbonate

A

dapsone
80-08-0

dapsone

B

4.4'-bis-<4-amino-benzenesulfonyl>-azoxybenzene

4.4'-bis-<4-amino-benzenesulfonyl>-azoxybenzene

C

C48H45N8O17P3S4(?)

C48H45N8O17P3S4(?)

N-hydroxydapsone
32695-27-5

N-hydroxydapsone

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; human recombinant NADH cytochrome b5 reductase; cytochrome b5 In dimethyl sulfoxide pH=7.4; Enzyme kinetics; Further Variations:; Reagents;
4,4'-di-N-acetylaminodiphenyl sulfoxide
5423-16-5

4,4'-di-N-acetylaminodiphenyl sulfoxide

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / 30 percent H2O2 / acetic acid / Heating
2: 80 percent / 10 percent HCl / 2.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium dichromate; aqueous sulfuric acid; acetic acid / 40 - 45 °C
2: aqueous hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid
2: acetone; aqueous potassium permanganate; acetic acid / Reagens 4: Kupfer(II)-sulfat
View Scheme
Multi-step reaction with 2 steps
1: potassium permanganate; aqueous acetic acid / bei Siedetemperatur
2: aqueous hydrochloric acid
View Scheme
With sodium molybdate; sodium tungstate; dihydrogen peroxide; acetic acid at 20 - 95℃; for 0.583333h; Temperature;12.4 g
Acetanilid
103-84-4

Acetanilid

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / SOCl2; AlCl3 / CS2 / 6 h / Heating
2: 70 percent / 30 percent H2O2 / acetic acid / Heating
3: 80 percent / 10 percent HCl / 2.5 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: aluminium chloride; carbon disulfide; thionyl chloride
2: potassium dichromate; aqueous sulfuric acid; acetic acid / 40 - 45 °C
3: aqueous hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: aluminium chloride / 160 °C / beim Eintragen in eine Schmelze
2: aqueous hydrochloric acid
View Scheme
4-acetylamino-4'-nitrodiphenyl sulfide
7467-51-8

4-acetylamino-4'-nitrodiphenyl sulfide

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KMnO4 / acetic acid
2: Sn/HCl
3: 15percent HCl
View Scheme
Multi-step reaction with 2 steps
1: sodium dichromate
2: iron / 90 - 95 °C / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: chromium (VI)-oxide; aqueous acetic acid / 40 - 50 °C
2: amalgamated zinc; aqueous acetic acid; formic acid / Hydrogenation
3: aqueous ethanolic hydrochloric acid
View Scheme
Multi-step reaction with 4 steps
1: chromium (VI)-oxide; aqueous acetic acid / 40 - 50 °C
2: amalgamated zinc; aqueous acetic acid; formic acid / Hydrogenation
3: acetic acid
4: aqueous hydrochloric acid
View Scheme
4-acetamidobenzenesulfinic acid
710-24-7

4-acetamidobenzenesulfinic acid

dapsone
80-08-0

dapsone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium acetate; cyclohexanol
2: iron; aqueous acetic acid / Hydrogenation
3: aqueous hydrochloric acid
View Scheme
Carbonyl fluoride
353-50-4

Carbonyl fluoride

dapsone
80-08-0

dapsone

C14H10F2N2O4S

C14H10F2N2O4S

Conditions
ConditionsYield
In acetone at 20℃; for 3h; Glovebox;100%
In acetone at 20℃; for 3h; Concentration;
formaldehyd
50-00-0

formaldehyd

dapsone
80-08-0

dapsone

Bis<(N,N-dimethylamino)phenyl> sulfone
33871-62-4

Bis<(N,N-dimethylamino)phenyl> sulfone

Conditions
ConditionsYield
With rhodium(III) chloride; Methyl formate; sodium acetate In methanol; water at 160℃; for 24h; Inert atmosphere;99%
With hydrogen; nickel In ethanol under 3102.9 Torr; for 2.5h;80%
ethanol
64-17-5

ethanol

dapsone
80-08-0

dapsone

4,4'-sulfonylbis(N-ethylaniline)

4,4'-sulfonylbis(N-ethylaniline)

Conditions
ConditionsYield
With [((5-Me)PyNPPh2)IrACHTUNGTRENUNG(cod)]; potassium tert-butylate In diethylene glycol dimethyl ether at 70℃; for 48h; Inert atmosphere;98%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.25h;98%
salicylaldehyde
90-02-8

salicylaldehyde

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.25h; Reagent/catalyst; Solvent; Temperature;98%
salicylaldehyde
90-02-8

salicylaldehyde

dapsone
80-08-0

dapsone

2,2'-{sulfonylbis[4,1-phenylenenitrilomethylidene]}diphenol
7251-84-5

2,2'-{sulfonylbis[4,1-phenylenenitrilomethylidene]}diphenol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform for 8h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;97.1%
In ethanol at 20℃;79.65%
N-(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)-N-[4-(4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]phenylsulfonyl)phenyl]amine
904692-00-8

N-(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)-N-[4-(4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]phenylsulfonyl)phenyl]amine

dapsone
80-08-0

dapsone

C54H36N4O4S2

C54H36N4O4S2

Conditions
ConditionsYield
In butan-1-ol for 30h; Heating;97%
methanol
67-56-1

methanol

dapsone
80-08-0

dapsone

4,4'-di(methylamino)diphenyl sulfone
7324-96-1

4,4'-di(methylamino)diphenyl sulfone

Conditions
ConditionsYield
With [((5-Me)PyNPPh2)IrACHTUNGTRENUNG(cod)]; potassium tert-butylate In diethylene glycol dimethyl ether at 70℃; for 48h; Inert atmosphere;97%
salicylaldehyde
90-02-8

salicylaldehyde

dapsone
80-08-0

dapsone

5,5'-[4,4'-sulfonylbis(4,1-phenylene)bis(diazene-2,1-diyl)]bis(2-hydroxybenzaldehyde)

5,5'-[4,4'-sulfonylbis(4,1-phenylene)bis(diazene-2,1-diyl)]bis(2-hydroxybenzaldehyde)

Conditions
ConditionsYield
Stage #1: dapsone With 1,3,5-trichloro-2,4,6-triazine; sodium nitrite In water at 20℃; for 0.05h; Sonication;
Stage #2: salicylaldehyde In water for 0.183333h;
97%
dapsone
80-08-0

dapsone

recorcinol
108-46-3

recorcinol

bis-[4-(2,4-dihydroxy-phenylazo)-phenyl]-sulfone
90116-36-2

bis-[4-(2,4-dihydroxy-phenylazo)-phenyl]-sulfone

Conditions
ConditionsYield
Stage #1: dapsone With 1,3,5-trichloro-2,4,6-triazine; sodium nitrite In water at 20℃; for 0.05h; Sonication;
Stage #2: recorcinol In water for 0.183333h;
97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.25h;97%
salicylaldehyde
90-02-8

salicylaldehyde

dapsone
80-08-0

dapsone

2,2'-{sulfonylbis[(p-phenylene)iminomethyl]}-diphenol
7251-84-5

2,2'-{sulfonylbis[(p-phenylene)iminomethyl]}-diphenol

Conditions
ConditionsYield
With formic acid In methanol Reflux;96%
With piperidine for 2h; Heating;
With ethanol
dapsone
80-08-0

dapsone

bis-(4-azido-phenyl)-sulfone
7300-27-8

bis-(4-azido-phenyl)-sulfone

Conditions
ConditionsYield
Stage #1: dapsone With 1-methyl-2-oxopyrrolidinium hydrogen sulfate In water at 20℃; for 0.0166667h; Grinding;
Stage #2: With sodium nitrite In water at 20℃; Grinding;
Stage #3: With sodium azide In water at 20℃; Grinding;
96%
Stage #1: dapsone With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h;
Stage #2: With sodium azide at 0 - 5℃;
85%
With sulfuric acid Diazotization.Eintragen der Diazoniumsalz-Loesung in eine gekuehlte wss. Loesung von Hydrazin-hydrat und Natriumacetat;
α,β-dibromo-α-methylpropionyl chloride
53089-03-5

α,β-dibromo-α-methylpropionyl chloride

dapsone
80-08-0

dapsone

2,3-Dibromo-N-{4-[4-(2,3-dibromo-2-methyl-propionylamino)-benzenesulfonyl]-phenyl}-2-methyl-propionamide
82820-79-9

2,3-Dibromo-N-{4-[4-(2,3-dibromo-2-methyl-propionylamino)-benzenesulfonyl]-phenyl}-2-methyl-propionamide

Conditions
ConditionsYield
96%
dapsone
80-08-0

dapsone

dapsone-D8
557794-38-4

dapsone-D8

Conditions
ConditionsYield
With water-d2; platinum on carbon; palladium 10% on activated carbon at 180℃; for 24h; Product distribution / selectivity;96%
With water-d2; platinum on carbon at 180℃; for 24h; Product distribution / selectivity;82%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

dapsone
80-08-0

dapsone

tetraethyl (sulfonylbis{4,1-phenyleneimino[(3-nitrophenyl)methylene]})bis(phosphonate)
1448137-82-3

tetraethyl (sulfonylbis{4,1-phenyleneimino[(3-nitrophenyl)methylene]})bis(phosphonate)

Conditions
ConditionsYield
With CeCl3·7H2O-SiO2 In neat liquid for 0.0666667h; Concentration; Reagent/catalyst; Solvent; Time; Kabachnik-Fields Reaction; Microwave irradiation;96%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

dapsone
80-08-0

dapsone

4’4’-bis(4-carboxybenzylidene)diaminodiphenylsulfone

4’4’-bis(4-carboxybenzylidene)diaminodiphenylsulfone

Conditions
ConditionsYield
In methanol at 30℃; for 18h;96%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(2-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(2-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.416667h;96%
acetic anhydride
108-24-7

acetic anhydride

dapsone
80-08-0

dapsone

acedapsone
77-46-3

acedapsone

Conditions
ConditionsYield
With acetic acid at 60℃; for 5h; Temperature;95%
With ZnAl2O4 nanoparticles at 20℃; for 0.0833333h; Neat (no solvent);92%
With acetic acid
maleic anhydride
108-31-6

maleic anhydride

dapsone
80-08-0

dapsone

4,4'-(diaminodiphenyl sulfone)bismaleimide
13102-25-5

4,4'-(diaminodiphenyl sulfone)bismaleimide

Conditions
ConditionsYield
With sodium acetate; acetic anhydride In acetone at 50℃; for 3h;95%
dapsone
80-08-0

dapsone

sulfonylbis(4,1-phenylene)bis(sulfamic acid)

sulfonylbis(4,1-phenylene)bis(sulfamic acid)

Conditions
ConditionsYield
With hydrogenchloride; chlorosulfonic acid In dichloromethane at 20℃; for 2.33333h; Cooling with ice;95%
dimedone
126-81-8

dimedone

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(4-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(9-(4-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.25h;95%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.333333h;95%
2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

dapsone
80-08-0

dapsone

1,1'-{sulfonylbis[(1,4-phenylene)iminomethyl]}bis(2-naphthol)
21708-77-0

1,1'-{sulfonylbis[(1,4-phenylene)iminomethyl]}bis(2-naphthol)

Conditions
ConditionsYield
With formic acid In methanol Reflux;94%
With zinc ferrite In water at 100℃; for 1.16667h;82%
With ethanol
With piperidine for 2h; Heating;
C20H18Cl2N2O6

C20H18Cl2N2O6

dapsone
80-08-0

dapsone

C32H30N4O9S

C32H30N4O9S

Conditions
ConditionsYield
With chloro-trimethyl-silane; p-dimethylaminocinnamaldehyde for 0.133333h; Reflux;94%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

dimedone
126-81-8

dimedone

dapsone
80-08-0

dapsone

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

10,10’-(sulfonylbis(4,1-phenylene))bis(3,3,6,6-tetramethyl-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione)

Conditions
ConditionsYield
With L-proline covalented silicapropyl mediated Fe3O4 nanoparticles In water at 20℃; for 0.333333h;94%
formic acid
64-18-6

formic acid

dapsone
80-08-0

dapsone

N,N'-(4,4'-sulfonylbis(4,1-phenylene))diformamide
6784-25-4

N,N'-(4,4'-sulfonylbis(4,1-phenylene))diformamide

Conditions
ConditionsYield
With Na+-MMT-[pmim]HSO4 In neat (no solvent) at 60℃; for 0.416667h; chemoselective reaction;93%

80-08-0Relevant articles and documents

Novel catalyst based on mono- and di-vanadium substituted Keggin polyoxometalate incorporated in poly(acrylic acid-co-acrylamide) polymer for the oxidation of sulfides

Frenzel, Romina A.,Romanelli, Gustavo P.,Pizzio, Luis R.

, p. 8 - 16 (2018)

Composite materials based on [PVxW12-xO40](3+x)? with x = 1 or 2 (PVW and PV2W respectively), included in poly(acrylic acid-co-acrylamide) gel (PAACA), were synthesized. The samples were characterized by different techniques such as FT-IR, 31P MAS-NMR, 51V-NMR, XRD, DTA-TGA, UV–vis DRS, and the acidic properties were estimated by means of potentiometric titration with n-butylamine. Samples containing 10, 20 and 30% (w/w) of polyoxotungstovanadate (POTV) were prepared by inclusion of the POTV in the polymer during its synthesis. According to Fourier transform infra-red and magic angle spinning-nuclear magnetic resonance studies, the predominat anion present in the samples is [PVxW12-xO40](3+x)?, and there is no evidence of its decomposition during the synthesis of hybrid materials and the drying step. According to XRD results, these anions are greatly dispersed in the PAACA or present as amorphous phases. UV–vis DRS data reveal that the samples synthesized using POTV with two vanadium atoms (PAACA-PV2W) exhibit lower values of absorption edge energy than those prepared using PVW (PAACA-PVW), which correlates with a higher oxidizing capacity. The potentiometric titration shows strong acid sites of the hybrid materials, and their number increases with the number of vanadium atoms and with the amount of POTV incorporated in the PAACA grid. The hybrid materials prepared by inclusion of POTV during the polymer synthesis exhibit appropriate physicochemical features to catalyze the oxidation of diphenyl sulfide (DPS) to its sulfone employing acetonitrile as solvent H2O2 as a green oxidant. The samples with 30% w/w of POVT, which show higher catalytic performance, are suitable for the DPS oxidation and can be reused without remarkable drop of their catalytic activity. Furthermore, they show high activity as a catalyst in the oxidation reaction of 4,4′-diamino diphenyl sulfide to the corresponding sulfone (dapsone) used for malaria treatment.

Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide

Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu

supporting information, p. 8691 - 8695 (2021/10/22)

A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.

C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin

, (2019/08/26)

An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.

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