621-18-1

Basic information

• Product Name: 3,3'-AZODIBENZOIC ACID
• Synonyms: AZOBENZENE-3,3'-DICARBOXYLIC ACID;AZONENZENE-3,3'-DICARBOXYLIC ACID;3,3'-AZODIBENZOIC ACID;AZOBENZENE-3,;3,3'-(Diazene-1,2-diyl)dibenzoic acid;3-[(3-carboxyphenyl)diazenyl]benzoic acid
• CAS NO: 621-18-1
• Molecular Formula: C₁₄H₁₀N₂O₄
• Molecular Weight: 270.24
• Mol File: 621-18-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 170-171 °C
• Boiling Point: 561.434°C at 760 mmHg
• Flash Point: 293.345°C
• Appearance: /
• Density: 1.354g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.635
• PKA: 3.54±0.10(Predicted)
• CAS DataBase Reference: 3,3'-AZODIBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-AZODIBENZOIC ACID(621-18-1)
• EPA Substance Registry System: 3,3'-AZODIBENZOIC ACID(621-18-1)

Safety Data

• Hazardous Substances Data: 621-18-1(Hazardous Substances Data)

Usage

General Description

3,3’-Azodibenzoic acid, also known as ADBA, is a yellow powder often used as a dye intermediate. It is a chemical compound with the molecular formula C14H10N2O4 and a molecular weight of 266.24 g/mol. ADBA is commonly employed in the production of azo dyes and pigments, as well as in the manufacturing of photographic emulsions. It is a versatile chemical with applications in various industries including textiles, printing, and photography. ADBA is known for its stable and insoluble nature in water, but it can be dissolved in organic solvents such as dimethylformamide and chloroform. However, it should be handled with care as it is considered a hazardous chemical and may cause skin and eye irritation upon contact.

InChI:InChI=1/C14H10N2O4/c17-13(18)9-3-1-5-11(7-9)15-16-12-6-2-4-10(8-12)14(19)20/h1-8H,(H,17,18)(H,19,20)

Upstream product

• 587-55-3 3,3'-azoxybis-benzoic acid 
• 121-92-6 3-nitrobenzoic acid 
• 621-17-0 3,3'-hydrazo-di-benzoic acid 
• 99-05-8 meta-aminobenzoic acid 
• 1843-35-2 3-azidobenzoic acid 
• 586-96-9 Nitrosobenzene 
• 99-09-2 3-nitro-aniline 
• 1743-37-9 diazotierte 3-Amino-benzoesaeure 
• 619-25-0 3-Nitrobenzyl alcohol 
• 143450-90-2 C₇H₅NO₂ 

Downstream Products

• 53171-92-9 3,3'-azo-di-benzoic acid dimethyl ester 
• 92-82-0 Phenazin 
• 621-17-0 3,3'-hydrazo-di-benzoic acid 
• 17557-76-5 4,4'-diamino-[1,1'-biphenyl]-2,2'-dicarboxylic acid 
• 1227476-15-4 Azobenzene 

Relevant articles and documents

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.

Correlation analysis of reactivity in the oxidation of anilines by nicotinium dichromate in nonaqueous media

The kinetics of oxidation of 15 para- and meta-substituted anilines by nicotinium dichromate (NDC) in different organic solvent media in the presence of p-toluenesulfonic acid (TsOH) has been investigated. The rate of the reaction is zero order with respect to substrate, first order in NDC, and is found to increase with increase in [TsOH]. The various thermodynamic parameters for the oxidation have been reported and discussed along with the validity of the isokinetic relationship. The specific rate of oxidizing species-anilines reaction (k2) correlates with Hammett's substituent constants affording negative reaction constants. The effect of paraand meta-substituents on the oxidation rates confirms to Swain et al.'s substituent constants F and R. both with negative reaction constants. The rate data failed to correlate with macroscopic solvent parameters such as εr, and E TN while showing satisfactory correlation with Kamlet-Taft's solvatochromic parameters (α. β. and π*).

Mechanism and reactivity in perborate oxidation of anilines in acetic acid

Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.