Description
4,4′-Diaminodiphenyldisulfide (CAS No. 722-27-0) is a high-purity organic compound with the molecular formula C12H12N2S2, widely utilized in advanced research and industrial applications. This aromatic disulfide features two primary amine functional groups, making it a versatile building block for polymerization, crosslinking, and functionalization reactions. Its IUPAC name, 4-[(4-aminophenyl)disulfanyl]aniline, reflects its symmetrical structure, where two aniline moieties are linked by a disulfide bridge. The compound is supplied as a crystalline solid with exceptional purity, ensuring reproducibility in synthetic and material science applications. Ideal for use in pharmaceuticals, polymer chemistry, and conductive materials, this reagent is packaged under inert conditions to maintain stability and performance.
Properties
- CAS Number: 722-27-0
- Complexity: 175
- IUPAC Name: 4-[(4-aminophenyl)disulfanyl]aniline
- InChI: InChI=1S/C12H12N2S2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H,13-14H2
- InChI Key: MERLDGDYUMSLAY-UHFFFAOYSA-N
- Exact Mass: 248.04419074
- Molecular Formula: C12H12N2S2
- Molecular Weight: 248.4
- SMILES: C1=CC(=CC=C1N)SSC2=CC=C(C=C2)N
- Topological: 103
- Monoisotopic Mass: 248.04419074
- Synonyms: 4,4′-Dithiodianiline, 722-27-0, 4-Aminophenyl disulfide, Benzenamine, 4,4′-dithiobis-, 4,4′-Dithiobisaniline, 4,4′-Diaminodiphenyl disulfide, p,p’-Dithiodianiline, Bis(p-aminophenyl) disulfide, Bis(4-aminophenyl) disulfide, Bis(p-aniline)disulfide, 4,4′-Diaminodiphenyldisulfide, Dithiobis(4-aminobenzene), 4,4′-Dithiobisbenzenamine, Aniline, 4,4′-dithiodi-, p,p’-Diaminodiphenyl disulfide, ANILINE, p,p’-DITHIODI-, EINECS 211-961-2, NSC-62984, 11D9715VB7, NSC-677451, VTI-8, DTXSID3061057, DTXCID9047257, 211-961-2, 4-[(4-aminophenyl)disulfanyl]aniline, 4-(4-aminophenyl)disulfanylaniline, p,p’-Dithiobisaniline, 4-Aminophenyldisulfide, 4,4′-disulfanediyldianiline, 4,4′-Diaminodiphenyl disulphide, NSC677451, Bis-(4-aminophenyl) disulfide, NSC62984, MFCD00007882, DTDA, p-p’-Dithiodianiline, 4,4′-Dithioaniline, 4-aminophenyidisulfide, di4-aminophenyl disulfide, bis(4-aminophenyl)disulfide, 4,4′-Dithiobis-benzenamine, NCIOpen2_008205, Di(4-aminophenyl) Disulfide, SCHEMBL34346, YSWG874, 4-Aminophenyl disulfide, 95%, 4-Aminophenyl disulfide, 98%, CHEMBL120723, UNII-11D9715VB7, STK720143, AKOS003244773, FD41550, {4-[(4-Aminophenyl)dithio]phenyl}amine, AC-12619, 4-(2-(4-aminophenyl)disulfanyl)benzenamine, DB-022663, DB-294710, 4-[(4-Aminophenyl)disulfanyl]phenylamine #, A9410, D0291, NS00037345, ST51038236, D89623, Q63409629, 4-Aminophenyl disulfide; 4-[(4-Aminophenyl)disulfanyl]aniline, 4,4′-Disulfanediyldianiline; 4,4′-Dithiobisaniline;4-Aminophenyl disulfide
Application
4,4′-Diaminodiphenyldisulfide serves as a critical precursor in the synthesis of polyimides and other high-performance polymers due to its dual amine reactivity. It is employed in crosslinking agents for elastomers and adhesives, enhancing thermal and mechanical properties. Researchers also utilize it in electrochemical applications, such as modifying electrode surfaces for biosensors or energy storage devices. Its disulfide bond offers dynamic covalent chemistry opportunities in self-healing materials.
Safety and Hazards
GHS Hazard Statements
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H335 (97.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statements
- P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Skin Irrit. 2 (100%)
- Eye Irrit. 2 (100%)
- STOT SE 3 (97.6%)
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