4,4′-Diaminodiphenylsulfone CAS 80-08-0
Category：Other Chemicals
Introduction
CAS:80-08-0,
80-08-0 – Names and Identifiers
| Name | 4-Aminophenyl sulfone |
| Synonyms | DDS EPORAL Dapsone 4,4′-DDS DISULONE NOVOPHONE AVLOSULFON SULFONA-MAE SULPHADIONE TIMTEC-BB SBB003168 4-Aminophenyl sulfone P-AMINOPHENYL SULFONE 4,4-Sulfonyldianiline diaminodiphenylsulfone P,P’-SULFONYLDIANILINE 4,4-sulphonyldianiline 4-Aminophenyl sulphone BIS(P-AMINOPHENYL)SULFONE BIS(4-AMINOPHENYL) SULFONE di(4-aminophenyl) sulphone 4,4′-Diaminodiphenylsulfone 4,4-Diaminodiphenyl sulfone 4,4-Diaminodiphenyl sulphone 4,4′-Diamino Diphenyl Sulfone 4,4′-Diaminodiphenyl sulphone 4,4′-Diamino Diphenyl Sulphone 4-((4-aminophenyl)sulfonyl)phenylamine 4,4′-Diaminodiphenyl sulfone for synthesis FREE SAMPLE NCV 4,4-DIAMINO DIPHENYL SULPHONE STD |
| CAS | 80-08-0 |
| EINECS | 201-248-4 |
| InChI | InChI=1/C12H10O2S.C7H6N2O5/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12;1-4-2-5(8(11)12)3-6(7(4)10)9(13)14/h1-10H;2-3,10H,1H3 |
| InChIKey | MQJKPEGWNLWLTK-UHFFFAOYSA-N |
80-08-0 – Physico-chemical Properties
| Molecular Formula | C12H12N2O2S |
| Molar Mass | 248.3 |
| Density | 1.2701 (rough estimate) |
| Melting Point | 175-177°C(lit.) |
| Boling Point | 511.7±35.0 °C(Predicted) |
| Water Solubility | <0.1 g/100 mL at 20 ºC |
| Solubility | 0.38g/l |
| Vapor Presure | 0.004Pa at 25℃ |
| Appearance | Crystalline Powder |
| Color | White to beige |
| Merck | 14,2822 |
| BRN | 788055 |
| pKa | pKb 13.0(at 25℃) |
| PH | 5.5-7.5 (H2O, 20℃)(saturated aqueous solution) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5950 (estimate) |
| Physical and Chemical Properties | Melting point 173-178°C water-soluble <0.1g/100 mL at 20°C |
| Use | The drug of choice for the treatment of leprosy, can also be combined with other anti-leprosy drugs |
80-08-0 – Risk and Safety
| Hazard Symbols | Xn – Harmful |
| Risk Codes | 22 – Harmful if swallowed |
| Safety Description | 22 – Do not breathe dust. |
| UN IDs | 3249 |
| WGK Germany | 1 |
| RTECS | BY8925000 |
| TSCA | Yes |
| HS Code | 29309070 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 4000 mg/kg |
80-08-0 – Standard
This product is 4,4 ‘-sulfonyl bis-aniline. Calculated as the dried product, the content of C12H12N202S shall not be less than 99.0%.
80-08-0 – Trait
- This product is white or off-white crystalline or crystalline powder; Odorless.
- This product is soluble in acetone, dissolved in methanol, slightly soluble in ethanol, almost insoluble in water; Dissolved in dilute hydrochloric acid.
melting point
The melting point of this product (General 0612) is 176~181°C.
80-08-0 – Differential diagnosis
- take this product, add methanol to make a solution containing 5ug per lml, according to UV-visible spectrophotometry (General 0401) determination, there is a maximum absorption at a wavelength of 261nm and 296Nm. The absorbance was 0.35-0.38 and 0.59-0.62, respectively.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 412).
- This product shows the identification reaction of aromatic first amines (General rule 0301).
80-08-0 – Exam
Related substances
take this product, add methanol to dissolve and dilute to make a solution containing about 10 mg per 1 ml, as a test solution; Take appropriate amount of precision, solutions containing about 20UG and 100ug per 1 ml, respectively, were prepared by dilution with methanol as Control Solutions (1) and (2). According to the thin layer chromatography (General 0502) test, draw 10ul of each of the above three solutions, respectively, on the same silica gel G thin layer plate, with toluene-acetone (2:1) as the developing solvent, dry, spray with 0.5% sodium nitrite 0. A 1 mol/L hydrochloric acid solution was then sprayed with a 0.1% dihydrochloric acid solution of naphthyl ethylenediamine after several minutes. Test solution such as impurity spots, compared with the control solution (1) of the main spot, not deeper; If there is more than 1~2 points, should not be deep in the control solution (2) the main spot.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 1.0% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
80-08-0 – Content determination
take this product about 0.25g, precision weighing, add water 30ml and hydrochloric acid solution (l-2)20ml, according to the permanent stop titration method (General rule 0701), with sodium nitrite titration solution (0.lmol/L) titration. Each l of sodium nitrite titration solution (0.1 mol/L) corresponds to 12.42mg of C12H12N202S.
80-08-0 – Category
anti-leprosy drugs.
80-08-0 – Storage
sealed storage.
80-08-0 – Dapsone tablets
This product contains dapsone (C12H12N202S) should be 93.0% to 107.0% of the label.
trait
This product is white or off-white.
identification
- take this product, add methanol to make a solution containing about 5ug dapsone per 1 ml, filter, take the filtrate according to dapsone under the identification (1) test, showed the same results.
- take an appropriate amount of fine powder of this product (approximately equivalent to dapsone O. 1G), 20ml of acetone was added, stirred, dapsone was dissolved, filtered, the filtrate was evaporated to dryness, and the residue showed the same reaction according to the identification (3) test under dapsone.
examination
- dissolution: according to the determination method of dissolution and release (General rule 0931, Method 1), the dissolution medium is 20ml of hydrochloric acid and water to 100 ml, and the rotation speed is rpm, operate according to the law, after 60 minutes, take the solution and filter, continue the filtrate (50mg specification) or take the continued filtrate accurately, A solution containing 50ug of dapsone per 1 mL (lOOmg specification) was prepared by quantitative dilution with dissolution medium as a test solution; An appropriate amount of dapsone reference was accurately weighed, the dissolution medium was added to dissolve and quantitatively dilute to prepare a solution containing about 50ug per 1 ml as a reference solution. Take 2ml of test solution and 2ml of reference solution respectively, put them in 25ml measuring flask, add 5ml of sodium hydroxide solution each, shake well, dilute with water to scale, shake well, the absorbance was measured at a wavelength of 0401 nm by ultraviolet-visible spectrophotometry (general), and the elution amount of each tablet was calculated. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product, precise weighing, fine grinding, precise weighing to take an appropriate amount (equivalent to dapsone 0.25g), according to the method under the dapsone determination. Each 1 ml of sodium nitrite titration solution (0.1 mol/L) corresponds to 12.42mg of C12H12N202S.
category
Same as dapsone.
specification
(l)50mg (2)100mg
storage
sealed storage.
80-08-0 – Reference Information
| LogP | 0.97 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 24, Sup 7) 1987 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | 4-4 ‘-diaminodiphenyl sulfone is a widely used chemical entity, it is used both as a hardener in the curing of epoxy resins and as a therapeutic agent for the treatment of bacterial infections in humans or animals, and has been approved as an antibiotic by the Food and Drug Administration since 1963. With regard to its use in human medicine, dapsone is in fact an effective antibiotic for the initial treatment of leprosy and subsequently also as an inhibitor of dermatitis herpetiformis. |
| Application | 4,4 ‘-diaminodiphenyl sulfone is an important aryl sulfone compound refined by high temperature and high pressure through ammoniation reaction. It is mainly used in the synthesis of polysulfone amide resin and other polymer synthetic materials, synthesis of a variety of acid azo dyes and disperse dyes. Can be used as epoxy resin curing agent and electrical insulation materials, textile equipment, can also be used as a catalyst, can also be used in the pharmaceutical industry for the treatment of leprosy and dermatitis herpetiformis, AIDS, etc. |
| preparation process | will melt 4,4 ‘-dichlorodiphenyl sulfone is pumped into the pipeline reactor at a flow rate of 140g/h via a high pressure pump, at the same time, the mixture of ammonia water and cuprous chloride with a mass fraction of 25% is also injected into the pipeline reactor together through a high-pressure pump at a flow rate of 800g/h (wherein the flow rate of cuprous chloride is 5.6g/h), the continuous aminolysis reaction is carried out at a pressure of 14Mpa and a temperature of 220 ℃, and the residence time of the reaction material in the high-pressure pipe is 20 minutes. The product is analyzed by liquid chromatography after being discharged under reduced pressure through a pressure reducing valve, the ammonolysis product contains 0.1% of 4,4’-dichlorodiphenyl sulfone, and the output is sent to the recovery unit to distill the excess ammonia and separate the crude 4,4 ‘-diaminodiphenyl sulfone; the crude product is dissolved in hydrochloric acid with a mass fraction of 10% at 30 ℃, decolorized with activated carbon, filtered, cooled to below 10 ℃, and adjusted to Ph 2-10% with sodium carbonate solution with a mass fraction of 2.5, centrifugal filtration, then washed with water until neutral, and dried to obtain finished product, purity of 99.5% 4,4’-diaminodiphenyl sulfone product (liquid chromatography analysis), the total yield of 97.1% (4,4 ‘-dichlorobis Phenyl sulfone meter). |
| Use | for the synthesis of polysulfonamide resin and other polymers, anti-leprosy drugs. used as medicine, polymer material intermediates for the treatment of leprosy drug of choice, can also be combined with other anti-leprosy drugs for the treatment of various types of leprosy. It is industrially used as a curing agent for epoxy resins. used as gas chromatography stationary liquid, organic synthesis intermediate and epoxy resin curing agent |
| production method | add 4,4 ‘-dichlorodiphenyl sulfone, ketone powder, methylene chloride and ammonia water into the autoclave, heat with stirring, under the pressure of 170~202 ℃ and 3MPA, the reaction was carried out for 14h, then the temperature was lowered to 60 ℃, filtered, washed with water and dried to obtain the crude product 4,4’-diaminodiphenyl sulfone. According to the purpose of the product, the crude product is refined. For example, the crude product can be dissolved in 10% hydrochloric acid, decolorized with activated carbon, filtered, cooled to below 10 ℃, adjusted to Ph 2~2.5 with sodium carbonate solution, and centrifuged and filtered, after washing with water until neutral, the product is obtained by drying. The yield was more than 78%. (1) with p-nitrochlorobenzene and p-aminobenzene sulfonic acid as raw materials (2) with p-nitrochlorobenzene as raw materials (3) with p-chlorobenzene sulfonyl chloride and chlorobenzene as raw materials |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 1000 mg/kg; Oral-mouse LD50: 250 mg/kg |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| fire extinguishing agent | carbon dioxide, sand, dry powder |
| Occupational Standard | SEL 5 mg/m3 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
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