103-18-4

Basic information

• Product Name: 4-Amino-4'-hydroxyazobenzene
• Synonyms: 4-[(4-aminophenyl)azo]phenol;4'-Hydroxy-4-aminoazobenzene;4-(4-Hydroxyphenylazo)aniline;4-Amino-4'-hydroxyazobenzene;4'-Aminoazobenzene-4-ol;4'-Hydroxyazobenzene-4-amine;p-[(p-Aminophenyl)azo]phenol
• CAS NO: 103-18-4
• Molecular Formula: C₁₂H₁₁N₃O
• Molecular Weight: 213.23524
• EINECS: 203-085-4
• Mol File: 103-18-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 185-190 °C (decomp)(Solv: ethyl acetate (141-78-6))
• Boiling Point: 353.22°C (rough estimate)
• Flash Point: 193.9°C
• Appearance: /
• Density: 1.1594 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6340 (estimate)
• PKA: 8.85±0.15(Predicted)
• CAS DataBase Reference: 4-Amino-4'-hydroxyazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-4'-hydroxyazobenzene(103-18-4)
• EPA Substance Registry System: 4-Amino-4'-hydroxyazobenzene(103-18-4)

Safety Data

• Hazardous Substances Data: 103-18-4(Hazardous Substances Data)

Usage

General Description

4-Amino-4'-hydroxyazobenzene is a member of the azobenzene class of compounds and is characterized by its distinctive azo bond (-N=N-) connecting two aromatic rings. It is commonly known as p-aminoazophenol and is used primarily as a dye intermediate in the production of azo dyes, which are widely employed in the textile and printing industries to impart vibrant colors to fabrics and materials.

InChI:InChI=1/C12H11N3O/c13-9-1-3-10(4-2-9)14-15-11-5-7-12(16)8-6-11/h1-8,16H,13H2

Upstream product

• 5302-39-6 N-(4-((4-hydroxyphenyl)diazenyl)phenyl)acetamide 
• 14368-49-1 p-nitrobenzenediazonium 
• 108-95-2 phenol 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 547-58-0 methyl orange 
• 1435-60-5 4-(4'-hydroxyphenylazo)nitrobenzene 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 5302-39-6 N-(4-((4-hydroxyphenyl)diazenyl)phenyl)acetamide 
• 1373771-76-6 C₂₀H₂₅N₃O₃ 
• 21811-64-3 4,4'-p-phenylene-bis-azo-di-phenol 
• 1119750-25-2 2-acetyl-2-ethoxycarbonyl-1-[4-(4-hydroxyphenylazo)phenyl]-3-(4-dimethylaminophenyl)aziridine 
• 316365-01-2 6-O-[(4-Aminophenylazo)phenyl]-permethylated α-cyclodextrin 
• 106-51-4 p-benzoquinone 
• 15658-50-1 4-(4-sulfooxy-phenylazo)-aniline 

Relevant articles and documents

Microwave synthesis of a photocatalytically active SnO-based material

Tin(II) oxide nanopowder has been prepared through microwave processing of an ammoniacal Sn6O4(OH)4 suspension, and the effect of synthesis duration on the surface morphology, acid-base properties, and photocatalytic activity of the SnO has been examined. The results demonstrate that the surface morphology plays a key role in determining the photocatalytic activity of powder SnO for methyl orange photo-degradation.

Stimuli responsive materials supported by orthogonal hydrogen and halogen bonding or i···alkene interaction

Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye I-azo-NO2, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As far as compound I–azo–NH–MMA is concerned, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures showing the same I···CH2=C contact. For all compounds, an19F-NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, the intermediate I–azo–NH2 also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design future multi-stimuli responsive materials for highly functional devices.

COLORING COMPOSITION, DICHROIC DYE COMPOUND, LIGHT ABSORPTION ANISOTROPIC FILM, LAMINATE, AND IMAGE DISPLAY DEVICE

A dichroic dye compound has an excellent alignment property when used in a light absorption anisotropic film, and has excellent solubility. A coloring composition contains the dichroic dye compound having a structure represented by Formula (1). In Formula (1), A and B represent a crosslinkable group, a and b are 0 or 1, and a+b is not less than 1. L1 and L2 represent a monovalent substituent, a single bond, or a divalent linking group. Each of Ar1 to Ar3 represents an aromatic hydrocarbon group or heterocyclic group. R1 to R3 represent a monovalent substituent. k represents an integer of 1 to 4. n1, n2, and n3 represent an integer of 0 to 4. In a case where k is 1, n1+n2+n3 is not less than 0, and in a case where k is not less than 2, n1+n2+n3 is not less than 1.