Basic information
- CAS
722-27-0- Standard SMILES
Nc1ccc(SSc2ccc(N)cc2)cc1- InChIKey
MERLDGDYUMSLAY-UHFFFAOYSA-N- Molecular formula
- C12H12N2S2
- Average molar mass
- 248.4 g/mol
- Monoisotopic mass
- 248.04419074
Names & identifiers
- Preferred name
- 4-Aminophenyl disulfide
- IUPAC
- 4-[(4-aminophenyl)disulfanyl]aniline
- English name
- 4,4'-Dithiodianiline
- Molecular formula
- C12H12N2S2
- Molecular weight
- 248.37
Names & synonyms
4,4'-Dithiodianiline722-27-04-Aminophenyl disulfidep,p'-Dithiobisaniline4,4'-DiaminodiphenyldisulfideVTI-811D9715VB7NSC-677451DTXSID3061057NSC-62984RefChem:506608DTXCID9047257
Show more names
4-aminophenylP-AMINOPHENYL DISULFIDEDithioaniline4,4'-Dithio-Aniline4,4’-dithiodi-anilinp,p’-dithiodi-anilinp,p’-dithiodianilinep-p'-Dithiodianiline
211-961-24-[(4-aminophenyl)disulfanyl]anilineBenzenamine, 4,4'-dithiobis-4,4'-disulfanediyldianiline4,4'-DithiobisanilineBis(p-aminophenyl) disulfideBis(4-aminophenyl) disulfide4,4'-Diaminodiphenyl disulfide
Database identifiers
- CAS
722-27-0- PubChem CID
- 12875
- DTXSID
DTXSID3061057- ChEMBL
CHEMBL120723- UNII
- 11D9715VB7
- EC Number
- 211-961-2
- Nikkaji
- J6.950G
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 175
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 77 · 77-78 °C(lit.)
- Boiling point
- 447 · 447.0±30.0 °C(Predicted)
- Density
- 1.2716 · 1.2716 (rough estimate)
- refractive index
- 1.57 · 1.5700 (estimate)
- solubility
- soluble in Methanol
- form
- powder to crystal
- pka
- 4.1 · 4.10±0.10(Predicted)
- color
- White to Yellow to Green
- Stability
- Stable. Incompatible with acids, acid chlorides, acid anhydrides, chloroformates, strong oxidizing agents. Sensitive to air.
- 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
- InChIKey
- MERLDGDYUMSLAY-UHFFFAOYSA-N
- SMILES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
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 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BX9580000
- hs_code
- 29309090
- Toxicity
- mma-sat 100 mg/plate MUREAV 67,123,79
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P501-P261-P271-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P304+P340+P312-P403+P233-P405
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzenamine, 4,4'-dithiobis-: ACTIVE
Applications
Uses4-Aminophenyl disulfide can be used as: A crosslinker in the synthesis of self-healing poly(urea-urethane) elastomers because of its quantitative healing efficiency. These self-healing materials find applications in various fields such as drug delivery, wound healing, and tissue engineering, electronics, aerospace, and coatings. A hardener in the formulation of re-processable, repairable, and recyclable epoxy networks due to the presence of dynamic disulfide bonds, which enable the epoxy networks to undergo chemical recycling. These epoxy networks are widely used in various applications which include, composite materials, coatings, adhesives, and fiber-reinforced thermoset composites. A crosslinking agent for the development of epoxy vitrimers and carbon fiber composites with enhanced mechanical properties, multi-shape memory capabilities for the potential applications in high-performance materials.4-Aminophenyl disulfide can also be used in the following:Bioconjugation: The amine group can react with carboxylic acids or their derivatives, making it useful for conjugating biomolecules like proteins and peptides. This is particularly valuable in developing targeted drug delivery systems where the drug is directly linked to a molecule th at can home in on cancer cells or other disease sites.Diagnostic Agents: It can be used to modify surfaces of diagnostic devices, such as biosensors. They can help in the immobilization of biomolecules on sensor surfaces, improving the sensitivity and specificity of detection.
Upstream & downstream products
Upstream raw materials
Suppliers86 total
Related reactions
6 records
Compound notes
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