1,3,5-Triazine

1,3,5-Triazine  | 1,3,5-Triazine | 1,3,5-Triazine

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Names
Preferred IUPAC name

1,3,5-Triazine[1]

Other names

sym-Triazine
s-Triazine
Cyanidine
Hydrogen cyanide trimer
Vedita

Identifiers

CAS Number

* 290-87-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:30259 Y

ChEMBL |

* ChEMBL15698 Y

ChemSpider |

* 8905 Y

EC Number |

* 206-028-1

PubChem CID

* 9262

RTECS number |

* XY2957000

UNII |

* 8B5F4CM81E Y

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

SMILES

* n1cncnc1

Properties

Chemical formula

| C3H3N3
Molar mass | 81.08 g/mol
Appearance  | White crystalline solid
Melting point |  81 to 83 °C (178 to 181 °F; 354 to 356 K)
Structure

Molecular shape

| planar

Dipole moment

| zero
Hazards
Main hazards | Sensitive to water
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H302, H314, H315, H335, H360

GHS precautionary statements

| P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P308+313, P310, P312, P321, P330, P332+313, P362, P363, P403+233, P405
Related compounds

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
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—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

## Contents

* 1 Preparation
* 2 Applications
* 2.1 Triazine derivatives
* 3 References

## Preparation

Symmetrical 1,3,5-triazines are prepared by trimerization of certain nitriles such as cyanogen chloride or cyanamide. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from benzonitrile and dicyandiamide.[2] In the Pinner triazine synthesis (named after Adolf Pinner)[3] the reactants are an alkyl or aryl amidine and phosgene.[4][5] Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core.[6]

Amine-substituted triazines called Guanamines are prepared by the condensation of cyanoguanidine with the corresponding nitrile:[7]

(H2N)2C=NCN + RCN → (CNH2)2(CR)N3

## Applications

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.[8]

### Triazine derivatives

N\- and C-substituted triazines are used industrially. The most common derivative of 1,3,5-triazine is 1,3,5-triazine-2,4,6-triamine, commonly known as melamine or cyanuramide. Another important derivative is 1,3,5-triazine-2,4,6-triol better known as cyanuric acid.

Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is the starting point for the manufacture of many herbicides such as Simazine and atrazine. Chlorinated triazines are the basis of an important family of reactive dyes, which are covalently attached to cellulosic materials.[9]

Methods for attaching reactive dyes to fibres (Cell = cellulose; R = chromophore).

Triazines are also found in pharmaceutical products.[10]

## References

1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 147. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
2. ↑ Benzoguanamine J. K. Simons and M. R. Saxton Organic Syntheses Coll. Vol. 4, p.78; Vol. 33, p.13 Article
3. ↑ A. Pinner, Ber. 23, 2919 (1890)
4. ↑ Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro
5. ↑ Schroeder, Hansjuergen; Grundmann, Christoph (1956). "Triazines. XIV. The Extension of the Pinner Synthesis of Monohydroxy-s-triazines to the Aliphatic Series. 2,4-Dimethyl-s-triazine1-3". Journal of the American Chemical Society 78 (11): 2447–2451. doi:10.1021/ja01592a028.
6. ↑ Shi, Baolu; Lewis, William; Campbell, Ian B.; Moody, Christopher J. (2009). "A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction". Organic Letters 11 (16): 3686–3688. doi:10.1021/ol901502u. PMID 19719202.
7. ↑ J. K. Simons; M. R. Saxton (1953). "Benzoguanamine". Org. Synth. 33: 13. doi:10.15227/orgsyn.033.0013.
8. ↑ Böhme, Roswitha M.; Dang, Qun (2008). "1,3,5-Triazine". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt158.pub2. ISBN 978-0471936237.
9. ↑ Tappe, Horst; Helmling, Walter; Mischke, Peter; Rebsamen, Karl; Reiher, Uwe; Russ, Werner; Schläfer, Ludwig; Vermehren, Petra (2000). "Reactive Dyes". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a22_651. ISBN 3527306730.
10. ↑ Aksenov, A. V.; Aksenova, I. V. (2009). "Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (Review)". Chemistry of Heterocyclic Compounds 45 (2): 130–150. doi:10.1007/s10593-009-0243-5.

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*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H314]: Causes severe skin burns and eye damage
*[H315]: Causes skin irritation
*[H335]: May cause respiratory irritation
*[H360]: May damage fertility or the unborn child
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up