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{{redirect|Vedita|the river|Vedița River}}
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
{{Chembox
! {{chembox header}} | 1,3,5-Triazine
| Watchedfields = changed
|-
| verifiedrevid = 477204630
| align="center" colspan="2" bgcolor="#ffffff" | ] ]
| Name = 1,3,5-Triazine
|-
| ImageFileL1 = 1,3,5-Triazin - 1,3,5-triazine.svg
! {{chembox header}} | General
| ImageNameL1 = 1,3,5-Triazine
|-
| ImageFileR1 = 1,3,5-triazine-3D-vdW.png
| ]
| 1,3,5-Triazine | ImageNameR1 = 1,3,5-Triazine
| PIN = 1,3,5-Triazine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
|-
| OtherNames = ''sym''-Triazine<br />''s''-Triazine<br />Cyanidine<br />Hydrogen cyanide trimer<br />Vedita
| Other names
|Section1={{Chembox Identifiers
| ''sym''-Triazine<br/>''s''-Triazine<br/>Cyanidine<br/>Hydrogen cyanide trimer<br/>Vedita
| SMILES = n1cncnc1
|-
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ]
| ChEBI_Ref = {{ebicite|correct|EBI}}
| C<sub>3</sub>H<sub>3</sub>N<sub>3</sub>
| ChEBI = 30259
|-
| ChemSpiderID = 8905
| ]
| InChI = 1/C3H3N3/c1-4-2-6-3-5-1/h1-3H
| C1=NC=NC=N1
| InChIKey = JIHQDMXYYFUGFV-UHFFFAOYAG
|-
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ]
| ChEMBL = 15698
| 81.08 g/mol
| EINECS = 206-028-1
|-
| PubChem = 9262
| Appearance
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| White crystalline solid
| StdInChI = 1S/C3H3N3/c1-4-2-6-3-5-1/h1-3H
|-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| ]
| StdInChIKey = JIHQDMXYYFUGFV-UHFFFAOYSA-N
|
| CASNo_Ref = {{cascite|correct|CAS}}
|-
| CASNo = 290-87-9
! {{chembox header}} | Properties
| UNII_Ref = {{fdacite|correct|FDA}}
|-
| UNII = 8B5F4CM81E
| ] and ]
| RTECS = XY2957000
| ? g/cm³, ? <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas -->
}}
|-
|Section2={{Chembox Properties
| ] in ]
| Formula = C{{sub|3}}H{{sub|3}}N{{sub|3}}
| ? g/100 ml (? °C) <!-- at least put miscible with, not soluble in -->
| MolarMass = 81.08 g/mol
|-
| Appearance = White crystalline solid
<!-- | Other solvents e.g. ], ] -->
| Density =
<!-- | solubility info on other solvents -->
| Solubility =
<!-- |- -->
| MeltingPtC = 81 to 83
| ]
| MeltingPt_notes =
| 81-83 °C (355 K)
| BoilingPt =
|-
}}
| ]
|Section3={{Chembox Structure
| ? °C (? K)
| MolShape = planar
|-
| Dipole = zero
! {{chembox header}} | Structure
}}
|-
|Section7={{Chembox Hazards
| ]
| MainHazards = Sensitive to water
| planar
| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}
|-
| GHSSignalWord = Danger
| ]
| HPhrases = {{H-phrases|302|314|315|335|360}}
| zero
| PPhrases = {{P-phrases|201|202|260|261|264|270|271|280|281|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|308+313|310|312|321|330|332+313|362|363|403+233|405|501}}
|-
| FlashPt =
! {{chembox header}} | Hazards
}}
|-
|Section8={{Chembox Related
| ]
| OtherFunction_label = ]
| ]
| OtherFunction =
|-
| OtherCompounds =
| Main ]s
}}
| Sensitive to water
}}
|-
| ]
| <!-- {{nfpa|4|4 ox|4}} These are set on "very dangerous" as default- adjust according to actual values -->
|-
| ]
| ? °C
|-
| ]
| ]: ? <br> ]: ?
|-
| ] number
| XY2957000
|-
! {{chembox header}} | ]
|-
| ]
| ], ], etc.
|-
| ]
| Phase behaviour<br>Solid, liquid, gas
|-
| ]
| ], ], ], ]
|-
! {{chembox header}} | Related compounds
|-
| Related ] <!-- PLEASE INSERT FUNCTIONAL GROUP (e.g. ]) FOR ORGANICS, please omit if not applicable -->
| ? <!-- Insert related organics e.g. on formaldehyde page put ] -->
|-
| Related compounds
<!-- A miscellaneous heading- use for covalent inorganics; e.g. for PCl<sub>3</sub> you would list PCl<sub>5</sub>, POCl<sub>3</sub>, PF<sub>3</sub>, PBr<sub>3</sub>, NCl<sub>3</sub> and AsCl<sub>3</sub>.
Please omit if not applicable -->
| ?
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their ]<br/>]</small>
|-
|}
The ] '''1,3,5-triazine''', also called '''s-triazine''', is an ] whose ] has a six-membered ] ] ring consisting of three ] ]s and three ] atoms. It is a common reagent, and readily form ]s, which are used as ] products and ]s.


'''1,3,5-Triazine''', also called '''''s''-triazine''', is an ] with the formula (HCN){{sub|3}}. It is a six-membered ] ] ring, one of several isomeric ]s. ''s''-Triazine —the "symmetric" isomer—and its derivatives are useful in a variety of applications.
== Chemistry ==


==Preparation==
The atoms in triazine rings are analogous to those in benzene rings, which makes triazines ]s like benzene.
Symmetrical 1,3,5-triazines are prepared by ] of certain nitriles such as ] or ]. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from ] and dicyandiamide.<ref>''Benzoguanamine'' J. K. Simons and M. R. Saxton ] Coll. Vol. 4, p.78; Vol. 33, p.13 {{Webarchive|url=https://web.archive.org/web/20120716191545/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0078 |date=2012-07-16 }}</ref> In the ] (named after ])<ref>A. Pinner, Ber. 23, 2919 (1890)</ref> the reactants are an alkyl or aryl ] and ].<ref>''Name reactions and reagents in organic synthesis'', Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro</ref><ref>{{cite journal | doi = 10.1021/ja01592a028| title = Triazines. XIV. The Extension of the Pinner Synthesis of Monohydroxy-s-triazines to the Aliphatic Series. 2,4-Dimethyl-s-triazine1-3| year = 1956| last1 = Schroeder| first1 = Hansjuergen| last2 = Grundmann| first2 = Christoph| journal = Journal of the American Chemical Society| volume = 78| issue = 11| pages = 2447–2451}}</ref> Insertion of an N-H moiety into a ] by a copper ], followed by treatment with ] also gives the triazine core.<ref>{{cite journal | doi = 10.1021/ol901502u| title = A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction| year = 2009| last1 = Shi| first1 = Baolu| last2 = Lewis| first2 = William| last3 = Campbell| first3 = Ian B.| last4 = Moody| first4 = Christopher J.| journal = Organic Letters| volume = 11| issue = 16| pages = 3686–3688| pmid = 19719202}}</ref>


Amine-substituted triazines called ]s are prepared by the condensation of ] with the corresponding ]:<ref>{{cite journal|journal=Org. Synth. |year=1953 |volume=33 |page=13 |doi=10.15227/orgsyn.033.0013 |title=Benzoguanamine |author1=J. K. Simons |author2=M. R. Saxton}}</ref>
The most common ] of 1,3,5-triazine is 2,4,6-triamino-1,3,5-triazine, commonly known as ] or ]. Another important derivative is 2,4,6-trihydroxy-1,4,5-triazine better known as ].
:(H{{sub|2}}N){{sub|2}}C=NCN + RCN → (CNH{{sub|2}}){{sub|2}}(CR)N{{sub|3}}


=== Isomers === ==Applications==
As a reagent in ], ''s''-triazine is used as the equivalent of ] (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the ], used to attach the ] to aromatic substrates.<ref>{{cite book | doi = 10.1002/047084289X.rt158.pub2| chapter = 1,3,5-Triazine| title = Encyclopedia of Reagents for Organic Synthesis| year = 2008| last1 = Böhme| first1 = Roswitha M.| last2 = Dang| first2 = Qun| isbn = 978-0471936237}}</ref>


===Triazine derivatives===
The 1,3,5-triazine is one of three ]s, the two other ]s being 1,2,3-triazine and 1,2,4-triazine.
''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 ] or cyanuramide. Another important derivative is 1,3,5-triazine-2,4,6-triol better known as ].
<!-- Henry Padleckas: I planned to write the ] article a long time ago and I made and uploaded the Triazine isomers pic into WikiCommons. Someone else pre-empted me in writing the Triazine article and put in his/her own pic, so mine have been sitting in WikiCommons unused until now. -->


] (2,4,6-trichloro-1,3,5-triazine) is the starting point for the manufacture of many ]s such as ] and ]. Chlorinated triazines are the basis of an important family of ]s, which are covalently attached to cellulosic materials.<ref name=Ullmann>{{cite book | doi = 10.1002/14356007.a22_651| chapter = Reactive Dyes| title = Ullmann's Encyclopedia of Industrial Chemistry| year = 2000| last1 = Tappe| first1 = Horst| last2 = Helmling| first2 = Walter| last3 = Mischke| first3 = Peter| last4 = Rebsamen| first4 = Karl| last5 = Reiher| first5 = Uwe| last6 = Russ| first6 = Werner| last7 = Schläfer| first7 = Ludwig| last8 = Vermehren| first8 = Petra| isbn = 3527306730}}</ref>
]
]
<br clear=left>


Triazines are also found in ] products.<ref>{{cite journal | doi = 10.1007/s10593-009-0243-5| title = Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (Review)| year = 2009| last1 = Aksenov| first1 = A. V.| last2 = Aksenova| first2 = I. V.| journal = Chemistry of Heterocyclic Compounds| volume = 45| issue = 2| pages = 130–150| s2cid = 94191027}}</ref>
==External links==


==References==
{{ChemicalSources}}
{{reflist}}


] {{DEFAULTSORT:Triazine, 1, 3, 5-}}
] ]

Latest revision as of 05:22, 22 September 2024

"Vedita" redirects here. For the river, see Vedița River.
1,3,5-Triazine
1,3,5-Triazine
1,3,5-Triazine
1,3,5-Triazine
1,3,5-Triazine
Names
Preferred IUPAC name 1,3,5-Triazine
Other names sym-Triazine
s-Triazine
Cyanidine
Hydrogen cyanide trimer
Vedita
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.481 Edit this at Wikidata
EC Number
  • 206-028-1
PubChem CID
RTECS number
  • XY2957000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H3N3/c1-4-2-6-3-5-1/h1-3HKey: JIHQDMXYYFUGFV-UHFFFAOYSA-N
  • InChI=1/C3H3N3/c1-4-2-6-3-5-1/h1-3HKey: 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
Occupational safety and health (OHS/OSH):
Main hazards Sensitive to water
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H302, H314, H315, H335, H360
Precautionary statements P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P362, P363, P403+P233, P405, P501
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. In the Pinner triazine synthesis (named after Adolf Pinner) the reactants are an alkyl or aryl amidine and phosgene. Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core.

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

(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.

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.

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

Triazines are also found in pharmaceutical products.

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 Archived 2012-07-16 at the Wayback Machine
  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. S2CID 94191027.
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