1,3,5-Triazine

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1,3,5-Triazine
IUPAC name 1,3,5-Triazine
Other names sym-Triazine s-Triazine Cyanidine Hydrogen cyanide trimer Vedita
Identifiers
CAS number	290-87-9 Y
ChemSpider	8905 Y
ChEBI	CHEBI:30259 Y
ChEMBL	CHEMBL15698 Y
RTECS number	XY2957000
Jmol-3D images	Image 1
SMILES n1cncnc1
InChI InChI=1S/C3H3N3/c1-4-2-6-3-5-1/h1-3H Y Key: JIHQDMXYYFUGFV-UHFFFAOYSA-N Y InChI=1/C3H3N3/c1-4-2-6-3-5-1/h1-3H Key: JIHQDMXYYFUGFV-UHFFFAOYAG
Properties
Molecular formula	C3H3N3
Molar mass	81.08 g/mol
Appearance	White crystalline solid
Melting point	81-83 °C (355 K)
Structure
Molecular shape	planar
Dipole moment	zero
Hazards
Main hazards	Sensitive to water
Related compounds
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 triazines. S-triazine and its derivatives are useful in a variety of applications.

Use in organic chemistry

As a reagent in organic synthesis, 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 herbicides, such as atrazine.

Substituted triazines

The most common derivative of 1,3,5-triazine is 2,4,6-triamino-1,3,5-triazine, commonly known as melamine 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.