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4,4'-Diaminodiphenylsulfone
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Name

4,4'-Diaminodiphenylsulfone

 EINECS 201-248-4
CAS No. 80-08-0 Density 1.361 g/cm3
PSA 94.56000 LogP 3.92700
Solubility <0.1 g/100 mL at 20℃ Melting Point 175-177 °C(lit.)
Formula C12H12N2O2S Boiling Point 511.7 °C at 760 mmHg
Molecular Weight 248.305 Flash Point 263.2 °C
Transport Information UN 3249 Appearance Off-white crystalline solid
Safety 22 Risk Codes 22
Molecular Structure Molecular Structure of 80-08-0 (4,4'-Diaminodiphenylsulfone) Hazard Symbols HarmfulXn
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;

Article Data 67

4,4'-Diaminodiphenylsulfone Synthetic route

1156-50-9

4-nitrophenyl sulfone

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
2050-48-8

4,4'-dibromodiphenyl sulfone

80-08-0

dapsone

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

bis-(4-azido-phenyl)-sulfone

80-08-0

dapsone

Conditions
ConditionsYield
With methanol; sodium sulfide for 0.0833333h;95%
80-07-9

4,4'-dichlorodiphenyl sulphone

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℃;
101-59-7

4-amino-4'-nitrodiphenyl sulfide

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
77-46-3

acedapsone

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
80-07-9

4,4'-dichlorodiphenyl sulphone

A

7146-68-1

4-(4-chloro-benzenesulfonyl)-aniline

B

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℃;
139-65-1

4,4'-thiobisaniline

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
106-40-1

4-bromo-aniline

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%
540-37-4

p-aminoiodobenzene

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'-Diaminodiphenylsulfone Chemical Properties


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

4,4'-Diaminodiphenylsulfone 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.

4,4'-Diaminodiphenylsulfone 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.

4,4'-Diaminodiphenylsulfone Safety Profile

Hazard Codes: HarmfulXn
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

4,4'-Diaminodiphenylsulfone 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.

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