4,4'-Diaminodiphenylsulfone

Modify Date: 2024-01-02 10:21:20

4,4'-Diaminodiphenylsulfone Structure
4,4'-Diaminodiphenylsulfone structure
 Common Name 4,4'-Diaminodiphenylsulfone
CAS Number 80-08-0 Molecular Weight 248.301
Density 1.4±0.1 g/cm3 Boiling Point 511.7±35.0 °C at 760 mmHg
Molecular Formula C12H12N2O2S Melting Point 175-177 °C(lit.)
MSDS Chinese USA Flash Point 263.2±25.9 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of 4,4'-Diaminodiphenylsulfone


Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae.Target: AntibacterialDapsone is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). Dapsone antagonized all of the I/R end points measured, showing a remarkable ability to decrease markers of damage through antioxidant, antiinflammatory, and anti-apoptotic effects [1]. As an antibacterial, dapsone inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthetase. Dapsone has anti-inflammatory and immunomodulatory effects [2].

 Names

Name dapsone
Synonym More Synonyms

 4,4'-Diaminodiphenylsulfone Biological Activity

Description Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae.Target: AntibacterialDapsone is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). Dapsone antagonized all of the I/R end points measured, showing a remarkable ability to decrease markers of damage through antioxidant, antiinflammatory, and anti-apoptotic effects [1]. As an antibacterial, dapsone inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthetase. Dapsone has anti-inflammatory and immunomodulatory effects [2].
Related Catalog
References

[1]. Diaz-Ruiz, A., et al., Antioxidant, antiinflammatory and antiapoptotic effects of dapsone in a model of brain ischemia/reperfusion in rats. J Neurosci Res, 2008. 86(15): p. 3410-9.

[2]. Begon, E., O. Chosidow, and P. Wolkenstein, [Disulone]. Ann Dermatol Venereol, 2004. 131(12): p. 1062-73.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 511.7±35.0 °C at 760 mmHg
Melting Point 175-177 °C(lit.)
Molecular Formula C12H12N2O2S
Molecular Weight 248.301
Flash Point 263.2±25.9 °C
Exact Mass 248.061951
PSA 94.56000
LogP 0.94
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.662
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
Water Solubility <0.1 g/100 mL at 20 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BY8925000
CHEMICAL NAME :
Aniline, 4,4'-sulfonyldi-
CAS REGISTRY NUMBER :
80-08-0
BEILSTEIN REFERENCE NO. :
0788055
LAST UPDATED :
199710
DATA ITEMS CITED :
46
MOLECULAR FORMULA :
C12-H12-N2-O2-S
MOLECULAR WEIGHT :
248.32
WISWESSER LINE NOTATION :
ZR DSWR DZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
112 mg/kg/4W-I
TOXIC EFFECTS :
Behavioral - muscle weakness Cardiac - pulse rate increase, without fall in BP Blood - oxidant related (GPD deficient) anemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
300 mg/kg/21W-I
TOXIC EFFECTS :
Blood - eosinophilia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - cyanosis Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
18 gm/kg/15Y
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Musculoskeletal - joints
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
36 mg/kg
TOXIC EFFECTS :
Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
196 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
313 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
225 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
357 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - domestic
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - muscle contraction or spasticity Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
1400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6750 mg/kg/45D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
910 mg/kg/26W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
44 mg/m3/17W-I
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Kidney, Ureter, Bladder - proteinuria Nutritional and Gross Metabolic - changes in chlorine
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
500 ug/m3/24H/13W-C
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
150 mg/kg/3D-I
TOXIC EFFECTS :
Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10800 mg/kg/45D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1890 mg/kg/30D-I
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20 gm/kg/80W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Blood - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1312 mg/kg/8W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39 gm/kg/78W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Blood - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 gm/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - changes in spleen Musculoskeletal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
78450 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Endocrine - thyroid tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
21840 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Blood - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2100 mg/kg
SEX/DURATION :
male 6 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Human Leukocyte
DOSE/DURATION :
4 mg/L
REFERENCE :
IJLEAG International Journal of Leprosy and Other Mycobacterial Diseases. (POB 1097, Bloomfield, NJ 07003) V.1- 1933- Volume(issue)/page/year: 43,41,1975 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,59,1980 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,59,1980 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,185,1987 TOXICOLOGY REVIEW IJDEBB International Journal of Dermatology. (J.B. Lippincott Co., E. Washington Sq., Philadelphia, PA 19105) V.9- 1970- Volume(issue)/page/year: 14,494,1975 TOXICOLOGY REVIEW JSIRAC Journal of Scientific and Industrial Research. (Pub. & Information Directorate, CSIR, Hillside Rd., New Delhi 110012, India) V.1-4, 1942-45; V.22- 1963- Volume(issue)/page/year: 34,521,1975 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-FINLAND;Carcinogen JAN 1993 OEL-RUSSIA:STEL 5 mg/m3 JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - T0798 No. of Facilities: 24 (estimated) No. of Industries: 2 No. of Occupations: 8 No. of Employees: 1510 (estimated) No. of Female Employees: 198 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S22
RIDADR 3249
WGK Germany 1
RTECS BY8925000
Packaging Group III
Hazard Class 6.1(b)
HS Code 29309070

 Synthetic Route

 Customs

HS Code 2921590090
Summary 2921590090. other aromatic polyamines and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Articles96

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 Synonyms

Aradur 976-1
Seikacure S
4,4'-Sulfonylbisbenzeneamine
Dapsone (USP)
Dapsone
1,1'-Sulfonylbis[4-aminobenzene]
ACZONE
4-(4-aminophenyl)sulfonylaniline
EINECS 201-248-4
4,4'-Sulfonyldianiline
Diaphenylsulfone (JAN)
MFCD00007887
4,4'-Diaminodiphenylsulfone
Benzenamine, 4,4'-sulfonylbis-
ZR DSWR DZ
4-Aminophenylsulfone
Bis(p-aminophenyl)sulfone
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