ChemicalBook > CAS DataBase List > 4,4'-Diaminodiphenylsulfone

4,4'-Diaminodiphenylsulfone

Product Name
4,4'-Diaminodiphenylsulfone
CAS No.
80-08-0
Chemical Name
4,4'-Diaminodiphenylsulfone
Synonyms
DDS;K509;wr448;DADPS;1358F;f1358;DADDS;Udolac;WR 448;EPORAL
CBNumber
CB0152851
Molecular Formula
C12H12N2O2S
Formula Weight
248.3
MOL File
80-08-0.mol
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4,4'-Diaminodiphenylsulfone Property

Melting point:
175-177 °C(lit.)
Density 
1.2701 (rough estimate)
refractive index 
1.5950 (estimate)
storage temp. 
-20°C Freezer
solubility 
0.38g/l
form 
Crystalline Powder
pka
pKb 13.0(at 25℃)
color 
White to beige
PH
5.5-7.5 (H2O, 20℃)(saturated aqueous solution)
Water Solubility 
<0.1 g/100 mL at 20 ºC
Merck 
14,2822
BRN 
788055
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
MQJKPEGWNLWLTK-UHFFFAOYSA-N
CAS DataBase Reference
80-08-0(CAS DataBase Reference)
NIST Chemistry Reference
Dapsone(80-08-0)
EPA Substance Registry System
Benzenamine, 4,4'-sulfonylbis-(80-08-0)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
22
RIDADR 
3249
WGK Germany 
1
RTECS 
BY8925000
TSCA 
Yes
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29051620
HS Code 
29309070
Hazardous Substances Data
80-08-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 4000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H320Causes eye irritation

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P307+P311IF exposed: call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
46158
Product name
Dapsone
Purity
VETRANAL , analytical standard
Packaging
250mg
Price
$45.3
Updated
2018/11/13
Sigma-Aldrich
Product number
1164008
Product name
Dapsone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$348
Updated
2018/11/13
TCI Chemical
Product number
D0089
Product name
Bis(4-aminophenyl) Sulfone
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$24
Updated
2018/11/22
TCI Chemical
Product number
D0089
Product name
Bis(4-aminophenyl) Sulfone
Purity
>98.0%(HPLC)(T)
Packaging
100g
Price
$54
Updated
2018/11/22
Alfa Aesar
Product number
A18976
Product name
4,4'-Diaminodiphenyl sulfone, 98%
Packaging
100g
Price
$41.3
Updated
2018/11/13
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4,4'-Diaminodiphenylsulfone Chemical Properties,Usage,Production

Chemical Properties

Off -White Crystalline Solid

Uses

An antibacterial used in the treatment of dermatitis herpetiformis

Uses

antibacterial, leprostatic, dermatitis herpetiformis suppressant

Uses

4,4'-diaminodiphenylsulfone be used for preparation polyimide and epoxy resin material.

Uses

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

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.

Indications

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.

brand name

Hansolar (ParkeDavis).

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

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.

Clinical Use

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.

Clinical Use

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.

4,4'-Diaminodiphenylsulfone Preparation Products And Raw materials

Raw materials

Preparation Products

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4,4'-Diaminodiphenylsulfone Suppliers

Hubei Gemvon New Materials Co., Ltd.
Tel
027-84295986
Fax
0713-8529996
Email
zzf@gemvon.com
Country
China
ProdList
4
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Wuhan Hezhong Bio-chemical Manufacture co ltd
Tel
021-68580715 / 18930710487
Email
nikki@pharm-china.com
Country
China
ProdList
2000
Advantage
55
Zhuhai JiaYi Biological Technology Co., Ltd.
Tel
18578209868 QQ2355327026
Fax
18578209868 QQ:2355327026
Email
steroidbest@hotmail.com
Country
China
ProdList
6512
Advantage
58
Yueyang Tianqing Biological Technology Co., Ltd.
Tel
15173087635
Email
tq201818@163.com
Country
CHINA
ProdList
35
Advantage
58
Wuhan Yuancheng Gongchuang Technology Co., Ltd.
Tel
18038040196
Fax
18038040196
Email
yc-tang@yccreate.com
Country
China
ProdList
6173
Advantage
58
Chengdu Yuanda chemical co.,ltd
Tel
+86-28-85356300 Mob:18980937689 Skype:chemscu QQ:435018036
Fax
+86-28-85356300
Email
chenquanxing@126.com
Country
China
ProdList
100
Advantage
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WUHAN YUANCHENG GONGCHUANG TECHNOLOGY CO.,LTD
Tel
18121080540
Email
hyt@ycphar.com
Country
China
ProdList
1990
Advantage
55
J & K SCIENTIFIC LTD.
Tel
400-666-7788 +86-10-82848833
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96506
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
Fax
+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)
Email
sh@meryer.com
Country
China
ProdList
40269
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
86-21-50328103 * 801、802、803、804 Mobile:18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15881
Advantage
69
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View Lastest Price from 4,4'-Diaminodiphenylsulfone manufacturers

Hebei Guanlang Biotechnology Co., Ltd.
Product
4,4'-Diaminodiphenylsulfone 80-08-0
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10 mt
Release date
2019-04-25
career henan chemical co
Product
4,4'-Diaminodiphenylsulfone 80-08-0
Price
US $2.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2018-08-15
Hebei Chisure Biotechnology Co., Ltd.
Product
4,4'-Diaminodiphenylsulfone 80-08-0
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500tons/month
Release date
2019-04-29

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