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| CAS No.: | 80-08-0 |
|---|---|
| Name: | 4,4'-Diaminodiphenylsulfone |
| Molecular Structure: | |
|
|
|
| Formula: | C12H12N2O2S |
| Molecular Weight: | 248.305 |
| 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; |
| EINECS: | 201-248-4 |
| Density: | 1.361 g/cm3 |
| Melting Point: | 175-177 °C(lit.) |
| Boiling Point: | 511.7 °C at 760 mmHg |
| Flash Point: | 263.2 °C |
| Solubility: | <0.1 g/100 mL at 20℃ |
| Appearance: | Off-white crystalline solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 22 |
| Transport Information: | UN 3249 |
| PSA: | 94.56000 |
| LogP: | 3.92700 |
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| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With copper(I) oxide; ammonium hydroxide In dimethyl sulfoxide at 90℃; for 20h; Sealed tube; | 98% |
| Conditions | Yield |
|---|---|
| With methanol; sodium sulfide for 0.0833333h; | 95% |
| Conditions | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
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IUPAC Name: 4-(4-Aminophenyl)sulfonylaniline
Molecular Formula: C12H12N2O2S
Molecular Weight: 248.30 g/mol
Canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
InChI: InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
EINECS: 201-248-4
Classification Code: Anti-Bacterial Agents; Anti-infective agents; Antibacterial [leprostatic]; Antibacterial [tuberculostatic]; Antimalarials; Antiparasitic Agents; Antiprotozoal Agents; Dermatitis herpetiformis suppressant; Drug / Therapeutic Agent; Enzyme Inhibitors; Folic acid antagonists; Human Data; Leprostatic agents; Mutation data; Reproductive Effect; Suppressant [dermatitis herpetiformis]; Tumor data
Melting Point: 175-177 °C(lit.)
Water Solubility: <0.1 g/100 mL at 20 °C
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Index of Refraction: 1.662
Molar Refractivity: 67.51 cm3
Molar Volume: 182.3 cm3
Surface Tension: 62.6 dyne/cm
Density: 1.361 g/cm3
Flash Point: 263.2 °C
Enthalpy of Vaporization: 78.27 kJ/mol
Boiling Point: 511.7 °C at 760 mmHg
Vapour Pressure of Dapsone (CAS NO.80-08-0): 1.39E-10 mmHg at 25 °C
Uses
Dapsone (CAS NO.80-08-0) is a pharmacological medication most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). It is also used to treat Pneumocystis carinii pneumonia (PCP) caused by Pneumocystis jiroveci. Dapsone is used in combination with pyrimethamine in the treatment of malaria.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | oral | 357mg/kg (357mg/kg) | Archives of Neurology and Psychiatry. Vol. 54, Pg. 319, 1945. | |
| child | TDLo | oral | 5mg/kg (5mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 1061, 1982/1983. |
| child | TDLo | oral | 37500ug/kg (37.5mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | Pediatric Emergency Care. Vol. 13, Pg. 127, 1997. |
| domestic animals - goat/sheep | LDLo | unreported | 200mg/kg (200mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | British Journal of Pharmacology and Chemotherapy. Vol. 5, Pg. 565, 1950. |
| guinea pig | LD50 | oral | 300mg/kg (300mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991. | |
| human | TDLo | oral | 18gm/kg/15Y (18000mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES MUSCULOSKELETAL: JOINTS | British Medical Journal. Vol. 1, Pg. 78, 1978. |
| mammal (species unspecified) | LD50 | unreported | 1400mg/kg (1400mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 43(9), Pg. 23, 1978. | |
| man | TDLo | oral | 36mg/kg (36mg/kg) | BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | Human Toxicology. Vol. 2, Pg. 507, 1983. |
| mouse | LD50 | intraperitoneal | 313mg/kg (313mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952. | |
| mouse | LD50 | intravenous | 225mg/kg (225mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952. | |
| mouse | LD50 | oral | 250mg/kg (250mg/kg) | American Review of Tuberculosis. Vol. 60, Pg. 62, 1949. | |
| mouse | LD50 | subcutaneous | 250mg/kg (250mg/kg) | American Review of Tuberculosis. Vol. 60, Pg. 62, 1949. | |
| rabbit | LD50 | skin | > 4gm/kg (4000mg/kg) | Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974. | |
| rat | LD50 | intraperitoneal | 196mg/kg (196mg/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 183, Pg. 36, 1970. |
| rat | LD50 | oral | 1gm/kg (1000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955. | |
| women | TDLo | oral | 18mg/kg (18mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | Acta Medica Scandinavica. Vol. 214, Pg. 215, 1983. |
| women | TDLo | oral | 28mg/kg (28mg/kg) | BLOOD: AGRANULOCYTOSIS | British Medical Journal. Vol. 286, Pg. 1244, 1983. |
| women | TDLo | oral | 112mg/kg/4W-I (112mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BLOOD: OXIDANT RELATED (GPD DEFICIENT) ANEMIA | Clinical and Experimental Dermatology. Vol. 20, Pg. 155, 1995. |
| women | TDLo | oral | 300mg/kg/21W- (300mg/kg) | BLOOD: EOSINOPHILIA | Lancet. Vol. 343, Pg. 860, 1994. |
Safety Profile
Hazard Codes: 
Xn
Risk Statements: 22
R22:Harmful if swallowed.
Safety Statements: 22
S22:Do not breathe dust.
RIDADR: 3249
WGK Germany: 1
RTECS: BY8925000
HazardClass: 6.1(b)
PackingGroup of Dapsone (CAS NO.80-08-0): III
Specification
Dapsone (CAS NO.80-08-0), its Synonyms are 1,1'-Sulfonylbis(4-aminobenzene) ; 1,1'-Sulphonylbis(4-aminobenzene) ; 4,4'-Dapsone ; 4,4'-Diaminodiphenyl sulfone ; 4,4'-Diaminodiphenyl suphone ; 4,4'-Sulfonylbisaniline ; 4,4'-Sulfonylbisbenzamine ; 4,4'-Sulfonylbisbenzenamine ; 4-Aminophenyl sulfone ; Benzenamine, 4,4'-sulfonylbis- ; Bis(4-aminophenyl) sulfone ; Aniline, 4,4'-sulfonyldi- . It is odorless white or creamy white crystalline powder and slightly bitter taste.