1,3,5-Triazine
Encyclopedia
1,3,5-triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazine
s. S-triazine and its derivatives are useful in a variety of applications.
, s-triazine is used as the equivalent of hydrogen cyanide (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the Gattermann reaction
, used to attach the formyl group to aromatic substrates.
It is a common reagent, and readily forms derivatives
, which are used as pharmaceutical products, as well as herbicide
s, such as atrazine
.
or cyanuramide. Trichloro-1,3,5-triazine (cyanuric chloride
) is the starting point for the manufacture of many herbicides such as Simazine
, as well as of many fiber reactive dyes
. Another important derivative is 2,4,6-trihydroxy-1,3,5-triazine better known as cyanuric acid
.
Triazine
A triazine is one of three organic chemicals, isomeric with each other, whose molecular formula is 333 and whose empirical formula is CHN.- Structure :...
s. S-triazine and its derivatives are useful in a variety of applications.
Use in organic chemistry
As a reagent in organic synthesisOrganic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
, s-triazine is used as the equivalent of hydrogen cyanide (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the Gattermann reaction
Gattermann reaction
The Gattermann rection, named for the German chemist Ludwig Gattermann, in organic chemistry refers to a reaction of hydrocyanic acid with an aromatic compound, in this case benzene, under catalysis with Friedel-Crafts catalyst .Catalyst used is Copper Powder in HX in the case of reaction of...
, used to attach the formyl group to aromatic substrates.
It is a common reagent, and readily forms derivatives
Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by some chemical or physical process. In the past it was also used to mean a compound that can be imagined to arise from another compound, if one atom is replaced with another atom or group of atoms, but modern...
, which are used as pharmaceutical products, as well as herbicide
Herbicide
Herbicides, also commonly known as weedkillers, are pesticides used to kill unwanted plants. Selective herbicides kill specific targets while leaving the desired crop relatively unharmed. Some of these act by interfering with the growth of the weed and are often synthetic "imitations" of plant...
s, such as atrazine
Atrazine
Atrazine, 2-chloro-4--6--s-triazine, an organic compound consisting of an s-triazine-ring is a widely used herbicide. Its use is controversial due to widespread contamination in drinking water and its associations with birth defects and menstrual problems when consumed by humans at concentrations...
.
Substituted triazines
The most common derivative of 1,3,5-triazine is 2,4,6-triamino-1,3,5-triazine, commonly known as melamineMelamine
Melamine is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses....
or cyanuramide. Trichloro-1,3,5-triazine (cyanuric chloride
Cyanuric chloride
Cyanuric chloride is the inorganic compound with the formula 3. This colorless solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride...
) is the starting point for the manufacture of many herbicides such as Simazine
Simazine
Simazine is a herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.-Physical properties:* Water solubility: 5 mg/L at 20 °C...
, as well as of many fiber reactive dyes
Reactive dye
In a reactive dye a chromophore contains a substituent that is activated and allowed to directly react to the surface of the substrate. Reactive dyes have good fastness properties owing to the bonding that occurs during dyeing....
. Another important derivative is 2,4,6-trihydroxy-1,3,5-triazine better known as cyanuric acid
Cyanuric acid
Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula 3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleaches, disinfectants, and herbicides...
.