Azo compounds are a diverse set of both natural and synthetic molecules containing at least one double-bonded nitrogen group (the “azo” group). Though there is an extremely wide range of azo compounds, the most common are pigments and dyes.
Bismarck Brown was the first commercial azo dye, which was produced from 1863. This sparked significant growth in the use of azo compounds during the 1880s, yielding a rich variety of additional azo dyes that were primarily used in the textile industry. Current applications for azo compounds include textiles, paints, printing ink, plastics, agrochemicals, pharmaceuticals, and more.
Fine Chemical Azo Compounds
Pigment and dye production generally do not require fine chemistry. However, for pharmaceutical, biomedical and agrochemical applications, fine chemical custom manufacturers play a critical role in the supply chain, addressing strict assay and impurity profiles.
Azo Compounds for Healthcare
Certain azo compounds are known to have antibiotic, antiviral, antifungal, antineoplastic, and cytotoxic properties. Fine chemical azo compounds can be a regulated starting material or an active pharmaceutical ingredient (API) for medications. Azo compounds can also be used to improve the delivery of a drug or for cellular staining to help the study of cells. Current research into naturally-occurring azo compounds is continually identifying potential new drugs to treat a wide variety of diseases.
Azo Compounds for Agrochemicals
Because of the way azo compounds react to light, there are many unique opportunities for their use in agrochemicals. For example, azobisisobutyronitrile (AIBN), an alkyl rather than an aromatic azo compound, is commercially important as a radical initiator in a wide variety of processes. Azo compounds have also been used to study how insecticides work by using azo compounds to turn the insecticide on and off with light for easier handling and more controlled experiments.
How are Fine Chemical Azo Compounds Produced?
There are several different methods of producing fine chemical azo compounds. One is through the use of azo coupling with a diazonium salt, formed by the oxidation of an aniline with nitric acid, and another aniline type molecule. Another route involves the oxidation of substituted hydrazines and the condensation of anilines with aryl nitro compounds, followed by oxidation of the azoxy intermediate. Finding the best pathway depends on a multitude of factors – a fine chemical manufacturing partner can help identify and refine the best way to obtain commercial quantities.
Azo Chemistry at CABB
CABB Group is a leading fine chemical custom manufacturer of starting materials, advanced intermediates, and active ingredients. CABB’s Custom Manufacturing business supports customers from 3 locations: Pratteln, Switzerland; Kokkola, Finland; and Jayhawk, USA, to offer creative solutions involving Azo chemistry.
If you would like more information about our products and services, simply contact a member of the CABB team today.
References:
https://www.ncbi.nlm.nih.gov/pubmed/29792144
https://aip.scitation.org/doi/pdf/10.1063/1.4945973
https://www.nature.com/articles/srep13962
