What is Triazine? - Derivatives & Synthesis

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

This lesson will focus on a class of nitrogen-containing heterocycles called triazines. We will get a brief overview of their structure, followed by some important derivatives, and wrap up with methods for their synthesis.

First Things First

What is one of the first things you have to do when you start to learn another language? If you said, ''Learn some vocabulary,'' you're correct! In many ways, learning organic chemistry is similar to learning another language. You have to learn the vocabulary first so you can understand the concepts. The vocabulary you are asked to learn can certainly seem VERY daunting and intimidating at first glance, but with a little practice and repetition, anyone can become proficient with organic chemistry lingo!

Triazines

The organic chemistry vocabulary term we are going to discuss today is a special class of organic compounds called triazines. Triazines are nitrogen-containing heterocycles. In organic chemistry, the term heterocycle refers to a ring system (or cyclic compound) that contains at least two different elements that make up the ring. A triazine is a heterocyclic structure that contains three nitrogen atoms and three carbon atoms. Let's get started and dive into some triazine explorations!

Structure

From a structural standpoint, there are three different triazine isomers and they differ from one another in the order of the nitrogen atoms relative to the carbons. An isomer refers to organic compounds that have the same chemical formula but different atom connectivity. The isomers are 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine.


Triazine isomers
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Notice how in the three isomers the nitrogen at the top of each ring is labeled atom number one, and then every other nitrogen or carbon is numbered relative to that position in a clockwise fashion. Another important structural feature of triazines is that they are aromatic. Aromatic means that there is a pattern of alternating double and single bonds all around the ring.

Triazine Derivatives

Triazine derivatives are well known. They are substituted at the carbon and nitrogen atoms. Melamine is a derivative of 1,3,5-triazine and contains three -NH2 groups, one bonded to each of the carbon atoms of the ring. Melamine finds applications as a fire-retardant agent and also is used as a pesticide in some cases.


Melamine: a 1,3,5-triazine derivative
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Another important triazine derivative is a compound called cyanuric chloride. This 1,3,5-triazine derivative is chlorinated at each of the three carbon atoms of the triazine ring and finds application as a precursor (building block or starting material) to a lot of popular pesticides.


Cyanuric chloride: a 1,3,5-triazine derivative
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Triazine Synthesis

Since triazine-containing compounds are not typically found in nature, they have to be made synthetically (man-made in the lab). Let's look at a couple of ways that triazines can be prepared.

Pinner Triazine Synthesis

2-hydroxyl-4,6-diaryltriazine is a substituted triazine that can be made by the reaction of an aromatic amidine and phosgene in a process called the Pinner triazine synthesis. The reaction is named after its inventor, Adolf Pinner, and was discovered in the late 1800's. An amidine is an organic building block that contains a carbon-nitrogen double bond as well as an amine functional group, and phosgene is a very reactive (and dangerous) organic compound that contains a carbon-oxygen double bond and two chlorine atoms. This reaction gives a 1,3,5-triazine product that is substituted at each of the three carbon atoms.


The Pinner triazine synthesis
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Notice that in this particular method, we need two molecules of the aromatic imidine for every one molecule of phosgene.

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