81-11-8

Basic information

• Product Name: 4,4'-Diamino-2,2'-stilbenedisulfonic acid
• Synonyms: Diaminostilbene-2,2'-disulfonic acid;4,4'-Diaminostilbene-2,2'-disulphonicacid(Amsonicacid);4,4'-Diamino-2,2'-st;Benzenesulfonic acid,2,2'-(1,2-ethenediyl)bis[5-aMino-;2,2’-(1,2-ethenediyl)bis[5-amino-benzenesulfonicaci;2,2’-(1,2-ethenediyl)bis[5-amino-Benzenesulfonicacid;2,2’-(1,2-ethenediyl)bis[5-amino-benzenesulfonicacid];2,2’-(1,2-ethylenediyl)bis(5-amino-benzenesulfonicaci
• CAS NO: 81-11-8
• Molecular Formula: C₁₄H₁₄N₂O₆S₂
• Molecular Weight: 370.4
• EINECS: 201-325-2
• Product Categories: Stilbenes;Fluorescent Labels & Indicators;Intermediates of Dyes and Pigments
• Mol File: 81-11-8.mol

Chemical Properties

• Melting Point: 300 °C
• Appearance: Cream to yellow-brown/Crystalline Powder
• Density: 1.4732 (rough estimate)
• Vapor Pressure: 1.3hPa at 25℃
• Refractive Index: 1.6510 (estimate)
• Storage Temp.: -20°C Freezer
• PKA: -1.58±0.50(Predicted)
• Water Solubility: <0.1 g/100 mL at 23 oC
• Stability: Stable. Combustible. Incompatible with iron, strong oxidizing agents.
• Merck: 14,595
• BRN: 629516
• CAS DataBase Reference: 4,4'-Diamino-2,2'-stilbenedisulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Diamino-2,2'-stilbenedisulfonic acid(81-11-8)
• EPA Substance Registry System: 4,4'-Diamino-2,2'-stilbenedisulfonic acid(81-11-8)

Safety Data

• Hazard Codes: C,Xn
• Statements: 34-22-36/37/38-20/21/22
• Safety Statements: 24/25-45-36/37/39-26-22
• RIDADR: UN 2583
• RTECS: WJ6603000
• TSCA: Yes
• Hazardous Substances Data: 81-11-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4,4'-Diamino-2,2'-stilbenedisulfonic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable building block for the development of new molecules with potential applications in various fields.
Used in Dye Manufacturing:
In the dye industry, 4,4'-Diamino-2,2'-stilbenedisulfonic acid is used as a raw material for the production of dyes. Its chemical properties allow it to be incorporated into dye molecules, contributing to their color and stability.
Used in Bleaching Agent Production:
4,4'-Diamino-2,2'-stilbenedisulfonic acid is also utilized in the manufacturing of bleaching agents. Its reactivity and reducing properties make it suitable for use in various bleaching processes, enhancing the whiteness and brightness of fabrics and other materials.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4,4'-Diamino-2,2'-stilbenedisulfonic acid is incompatible with iron. 4,4'-Diamino-2,2'-stilbenedisulfonic acid forms sparingly water-soluble, crystalline salts with many bisquaternary ammonium bases.

Fire Hazard

Flash point data for 4,4'-Diamino-2,2'-stilbenedisulfonic acid are not available; however, 4,4'-Diamino-2,2'-stilbenedisulfonic acid is probably combustible.

Upstream product

• 121-03-9 4-nitrotoluene-2-sulfonic acid 
• 1211962-72-9 4,4'-dinitrostilbene 2,2'-disulfonic acid 
• 119-72-2 4-nitro-4'-amino-stilbene-2,2'-disulphonic acid 
• 7647-01-0 hydrogenchloride 
• 16473-79-3 4',4'''-dinitro-4,4''-azo-bis-stilbene-2,2'-disulfonic acid 
• 7803-57-8 hydrazine hydrate 
• 111-46-6 diethylene glycol 
• 6404-60-0 4,4'-dinitrobibenzyl-2,2'-disulfonic acid 
• 7732-18-5 water 
• 108-88-3 toluene 
• 88-20-0 o-toluenesulfonic acid 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 56682-96-3 5,5'-bis-(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-2,2'-ethene-1,2-diyl-bis-benzenesulfonic acid 
• 58727-02-9 4,4'-bis-sulfanilylamino-stilbene-2,2'-disulfonic acid 
• 6421-83-6 4,4'-bis-(3-amino-benzoylamino)-stilbene-2,2'-disulfonic acid 
• 69851-86-1 5-amino-2-formyl-benzenesulfonic acid 
• 28097-15-6 trans-stilbene-disulfonic acid-(2,2') 
• 26092-49-9 4,4'-bis-hydrazino-stilbene-2,2'-disulphonic acid 
• 5136-34-5 6,6'-(ethane-1,2-diyl)bis(3-aminobenzenesuIfonic acid) 
• 7336-20-1 disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid 
• 56682-91-8 5,5'-bis-(4-amino-6-chloro-[1,3,5]triazin-2-ylamino)-2,2'-ethene-1,2-diyl-bis-benzenesulfonic acid 
• 26110-34-9 5,5'-bis-(4-chloro-6-methoxy-[1,3,5]triazin-2-ylamino)-2,2'-ethene-1,2-diyl-bis-benzenesulfonic acid 

Relevant articles and documents

Stilbene type compound as well as synthesis method and application thereof

The invention discloses a stilbene type compound as well as a synthesis method and application thereof, wherein the synthesis method comprises the steps: taking an intermediate 2 and an intermediate 4 as initiators, sequentially carrying out Wittig reaction, reduction reaction, amino protection reaction, condensation reaction, deprotection reaction and amidation reaction, and then refining to obtain the stilbene type compound. The synthesis process is high in controllability, used reagents are low in price, and the method is simple and easy to industrialize. The stilbene type compound can be used as a medicine for resisting tumors and viruses and treating fungal infection and cardiovascular and cerebrovascular diseases.

A reduction of nitro aromatic substituent amino aromatic of substituted method (by machine translation)

The invention relates to amino aromatic substituted object synthesis technology field, in particular to a process for preparing nitro aromatic substituent amino aromatic of substituted method. The method comprises the following steps, water, catalyst is added to the 1st in the reactor, and the reactor temperature, adding reducing iron, adjusting pH, at the same time added to the 1st nitro aromatic substituent in the reactor, thermal insulation reaction, to obtain a reaction liquid; regulating the reaction liquid of pH, thermal reaction, the addition of a stabilizing agent, containing the amino aromatic of substituted 1st solution and iron oxide black crude; adjusting the pH of the 1st solution, solid-liquid separation, obtained amino aromatic substituent. The present invention provides a process for the production of the method is simple, can be continuously produced, with high operation safety and higher selectivity, the reaction time is short, a yield as high as 90% or more, the product quality is good, the content of 98% or more. (by machine translation)

Nitrogen doped carbon supported iron catalysts for highly selective production of 4,4′-diamino-2,2′-stilbenedisulfonic acid

Nitrogen doped carbon supported iron catalysts were prepared from pyrolysis of a multidentate nitrogen ligand iron complex supported on chitosan at different temperature, and showed good performances in the reduction of 4,4′-dinitrostilbene-2,2′-disulfonic acid (DNS acid) to 4,4′-diamino-2,2′-stilbenedisulfonic acid (DSD acid) with hydrazine hydrate (N2H4·H2O) as reductant. Characterization results revealed that the iron is mainly present in the form of Fe2O3 and metallic iron nanoparticles. The doped N atoms functionalized as anchoring sites to stabilize iron nanoparticles, which endows the catalysts with excellent activity and superior reusability.

DSD acid preparation method

The invention relates to the field of chemical synthesis, in particular to a DSD acid preparation method. The DSD acid preparation method includes the steps that methylbenzene is subjected to sulfonation, purification and separation to obtain OTS, wherein the byproduct is PTS; OTS is subjected to mixed acid nitration to obtain PNTS; PNTS is subjected to chlorine oxidative condensation to obtain DNS; DNS is subjected to catalyzed hydrogeneration reduction to obtain the high-quality target product, namely DSD acid which can be directly used for synthesizing a fluorescent whitening agent. The synthesis method greatly reduces dangerousness of the process, greatly reduces generation of harmful byproducts and waste, particularly, does not generate a lot of carcinogenic intermediate, namely ortho-nitrotoluene, completely solves the nitration safety problem of the old technology, and has the advantages of being simple in step, high in yield and the like.

Preparation method of 4,4'-diamino diphenylethene-disulfonic acid

The invention discloses a preparation method of 4,4'-diamino diphenylethene-disulfonic acid. 4,4'-binitro diphenylethene-disulfonic acid or 4,4'-binitro diphenylethene-disulfonate serves as a raw material, the raw material and a supported catalyst are co-dispersed in a solvent, and 4,4'-diamino diphenylethene-disulfonic acid is prepared through a hydrogenation reaction. Based on the total mass of the supported catalyst, active ingredients in the supported catalyst comprise, by mass, 0.1-10% of platinum, 0-5% of ruthenium and 0-5% of iridium, wherein the mass fraction of ruthenium and the mass fraction of iridium cannot be 0 at the same time. According to the preparation method of 4,4'-diamino diphenylethene-disulfonic acid, the high-activity and high-selectivity supported catalyst is adopted, and the produced product reaches the China chemical industry standard HG/T 2279-2011.

Facile, mild and convenient preparation and characterization of some novel schiff base ligands from synthetic diamines and salicylaldehyde

Some novel Schiff base ligands have been prepared through condensation of salicylaldehyde with synthetic various primary diamines under mild reaction conditions. The used aromatic diamines were synthesized in good yields starting from low-cost commercially available materials. In these reactions, the Schiff base products have been afforded with excellent yields and appropriate reaction times. The structure of these ligands has been characterized by IR, 1H NMR and 13C NMR techniques.

Supported nano-sized gold catalysts for selective reduction of 4,4′-dinitrostilbene-2,2′-disulfonic acid using different reductants

Gold nanoparticles supported on three metal oxides, TiO2, Al2O3 and Fe2O3, were prepared by a modified precipitation-deposition method using urea as an additive. These catalysts were tested in chemoselective reduction of 4,4′-dinitrostilbene- 2,2′-disulfonic acid to 4,4′-diaminostilbene-2,2′-disulfonic acid. Three reagents, hydrogen, carbon monoxide, and sodium formate, were employed as reductants. It was found that >94% of the nitrostilbene was transformed into the aminostilbene without the reduction of olefinic group. In addition, these catalysts exhibited stable performance after regeneration by calcination at 400 °C for 5 h. This clean approach provides a promising application for synthesis of amino substituted stilbene sulfonic acid on an industrial scale.

SUSTAINABLE CHEMICAL PROCESS FOR REDUCTION OF NITRO COMPOUNDS (R-NO2) OR NITROSO COMPOUNDS (R-NO) CONTAINING SULPHONIC OR CARBOXYLIC GROUP INTO CORRESPONDING AMINO COMPOUNDS (R-NH2) WITH INHERENT RECYCLE OF ALL ACIDIC STREAMS GENERATED IN SYNTHESIS

The process of the present invention creates a sustainable and closed water loop allowing inherent recycles of all liquid streams generated in the process. The liquid streams generated during the process of the invention are inherently recycled completely, making the process of the present invention a zero liquid discharge process which is environmentally friendly and sustainable. This invention further relates to a sustainable chemical process of reduction of R- NO2 or R-NO into corresponding R-NH2 that produces environmentally friendly R-NH2 in good yields and selectivity with large of mother liquor recycle. The process has a wide scope in that it can be applied to a number of molecules.

Selective reduction of 4,4′-dinitrostilbene-2,2′-disulfonic acid catalyzed by supported nano-sized gold with sodium formate as hydrogen source

Gold nanoparticles supported on four different metal oxides were prepared and applied in the chemoselective reduction of 4,4′-dinitrostilbene-2, 2′-disulfonic acid (DNS). With sodium formate as hydrogen source, > 99% of the DNS was transformed into 4,4′-diaminostilbene-2,2′- disulfonic acid (DSD) without the reduction of olefinic group, which uncovers a clean synthetic approach for useful amino substituted stilbene sulfonic acids.

Reduction of 4,4′-dinitrostilbene-2,2′-disulfonic acid with hydrogen on raney nickel

Reduction of 4,4′-dinitrostilbene-2,2′-disulfonic acid with hydrogen in aqueous solution on Raney nickel yields a trisazo compound identical to Direct Yellow K dye.