Description

3,3′,4,4′-Tetraaminodiphenyl ether (CAS No. 2676-59-7) is a high-purity aromatic amine compound with the molecular formula C₁₂H₁₄N₄O. This tetrafunctional amine, also known by its IUPAC name 4-(3,4-diaminophenoxy)benzene-1,2-diamine, features two ortho-diaminobenzene groups linked by an ether bridge, making it a valuable building block for advanced polymer synthesis. The compound is supplied as a crystalline solid with ≥98% purity (HPLC), ideal for research applications requiring precise stoichiometry. Its unique structure enables participation in polycondensation reactions to form high-performance polyimides, polybenzimidazoles, and other thermally stable heterocyclic polymers. Proper storage under inert atmosphere at 2-8°C is recommended to prevent oxidation. Suitable for use as a crosslinking agent, epoxy hardener, or precursor for conductive polymers in electronics applications.

Properties

• CAS Number: 2676-59-7
• Complexity: 227
• IUPAC Name: 4-(3,4-diaminophenoxy)benzene-1,2-diamine
• InChI: InChI=1S/C12H14N4O/c13-9-3-1-7(5-11(9)15)17-8-2-4-10(14)12(16)6-8/h1-6H,13-16H2
• InChI Key: RQBIGPMJQUKYAH-UHFFFAOYSA-N
• Exact Mass: 230.11676108
• Molecular Formula: C12H14N4O
• Molecular Weight: 230.27
• SMILES: C1=CC(=C(C=C1OC2=CC(=C(C=C2)N)N)N)N
• Topological: 113
• Monoisotopic Mass: 230.11676108
• Synonyms: 3,3′,4,4′-Tetraaminodiphenyl ether, 4,4′-Oxybis(benzene-1,2-diamine), 1,2-Benzenediamine, 4,4′-oxybis-, 4,4′-Oxybis(1,2-benzenediamine), A8NR6PP85T, EINECS 220-226-5, DTXSID90181271, 3,4,3′,4′-TETRAAMINODIPHENYL ETHER, DTXCID00103762, 2676-59-7, 4-(3,4-diaminophenoxy)benzene-1,2-diamine, BIM-0011447.P001, 4,4′-oxydibenzene-1,2-diamine, CBMicro_011304, UNII-A8NR6PP85T, bis(3,4-diaminophenyl)ether, cid_75887, SCHEMBL296169, CHEMBL1448416, BDBM42079, SMSF0003872, STK072248, 3,3′,4,4′-Tetraminodiphenyl ether, AKOS000491323, CB14762, ST039912, 4-(3,4-Diaminophenoxy)-1,2-benzenediamine, CS-0336112, NS00028193, [2-amino-4-(3,4-diaminophenoxy)phenyl]amine, 4-[3,4-bis(azanyl)phenoxy]benzene-1,2-diamine

Application

3,3′,4,4′-Tetraaminodiphenyl ether serves as a critical monomer for synthesizing thermally stable polyimide films used in flexible printed circuits and aerospace composites. The compound’s tetrafunctional nature enables creation of highly crosslinked polymer networks with exceptional mechanical strength and chemical resistance. Researchers utilize this diamine to develop advanced adhesives and encapsulants for high-temperature electronic applications. In materials science, it functions as a precursor for conductive polymers when combined with appropriate dianhydrides or other electrophilic monomers.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P233, P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Resp. Sens. 1 (100%)
• STOT SE 3 (100%)

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