CAS No.80-08-0,4,4'-Diaminodiphenylsulfone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	80-08-0
Name:	4,4'-Diaminodiphenylsulfone
Article Data:	67

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

Synthetic route

: 1156-50-9
4-nitrophenyl sulfone

: 80-08-0
dapsone

Conditions

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

: 2050-48-8
4,4'-dibromodiphenyl sulfone

: 80-08-0
dapsone

Conditions

Conditions	Yield
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

Conditions	Yield
With methanol; sodium sulfide for 0.0833333h;	95%

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

: 80-08-0
dapsone

Conditions

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℃;

: 101-59-7
4-amino-4'-nitrodiphenyl sulfide

: 80-08-0
dapsone

Conditions

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

: 77-46-3
acedapsone

: 80-08-0
dapsone

Conditions

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

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

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

B: 80-08-0
dapsone

Conditions

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℃;

: 139-65-1
4,4'-thiobisaniline

: 80-08-0
dapsone

Conditions

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

: 106-40-1
4-bromo-aniline

: 80-08-0
dapsone

Conditions

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%

: 540-37-4
p-aminoiodobenzene

: 80-08-0
dapsone

Conditions

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%

Raw Materials

80-09-1

103-84-4

66294-58-4

121-60-8

100-66-3

4462-61-7

64-17-5

106-53-6

Downstream Products

2050-48-8

23038-36-0

565-20-8

127-63-9

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Chemistry

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: Harmful 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.