Description
Benzenediazonium, 2-methoxy-4-(phenylamino)-, sulfate (1:1) (CAS No. 36305-05-2) is a highly specialized diazonium salt with the molecular formula C13H13N3O5S. This compound is widely utilized in organic synthesis, particularly in diazo coupling reactions, where it serves as a critical intermediate for the preparation of azo dyes, pigments, and other functional materials. Its unique structure, featuring a methoxy and phenylamino substituent, allows for selective reactivity in electrophilic aromatic substitutions. The sulfate counterion enhances stability and solubility in aqueous systems, making it suitable for controlled reactions in both academic and industrial settings. Supplied as a high-purity solid, this reagent is ideal for researchers requiring precision in photochemistry, surface modification, and polymer science applications.
Properties
- CAS Number: 36305-05-2
- Complexity: 356
- IUPAC Name: 4-anilino-2-methoxy-benzenediazonium;hydrogen sulfate
- InChI: InChI=1S/C13H12N3O.H2O4S/c1-17-13-9-11(7-8-12(13)16-14)15-10-5-3-2-4-6-10;1-5(2,3)4/h2-9,15H,1H3;(H2,1,2,3,4)/q+1;/p-1
- InChI Key: HBDLDBQEQKQUPI-UHFFFAOYSA-M
- Exact Mass: 323.05759170
- Molecular Formula: C13H13N3O5S
- Molecular Weight: 323.33
- SMILES: COC1=C(C=CC(=C1)NC2=CC=CC=C2)[N+]#N.OS(=O)(=O)[O-]
- Topological: 135
- Monoisotopic Mass: 323.05759170
- Synonyms: 36305-05-2, Benzenediazonium, 2-methoxy-4-(phenylamino)-, sulfate (1:1), DTXSID60889398, EINECS 252-959-1, DTXCID201028659, 4-Diazo-3-methoxydiphenylamine Sulfate, 2-Methoxy-4-(phenylamino)benzenediazonium hydrogensulfate, Diazomethoxydiphenylaminesulfate, SCHEMBL5698877, 2-methoxy-4-(phenylamino)benzenediazonium hydrogen sulfate, MFCD00083004, D2285, 2-methoxy-4-(phenylamino)-benzenediazonium bisulfate, 2-methoxy-4- (phenylamino)benzenediazonium hydrogen sulfate
This compound is primarily employed as a photoactive diazonium salt in photolithography and surface functionalization. It enables covalent bonding to substrates such as metals, polymers, and glass, facilitating the creation of self-assembled monolayers (SAMs). Researchers also use it for synthesizing azo dyes with tailored optical properties. Its stability and reactivity make it valuable in electrochemical and sensor applications.
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 (92.9%): 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 (92.9%)
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