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== Reactions ==
== Reactions ==
<ref name=":1">{{Cite journal|last2=Poesche|first2=W. H.|last3=Higgins|first3=D.|last4=Heard|first4=D. D.|title=458. 1,2,3-Benzothiadiazole. Part I. Nitro-, amino-, and hydroxy-derivatives|url=https://pubs.rsc.org/en/content/articlelanding/1962/jr/jr9620002374|journal=Journal of the Chemical Society (Resumed)|year=1962|language=en|volume=|pages=2374–2379|doi=10.1039/JR9620002374|issn=0368-1769|via=|last1=Ward|first1=E. R.}}</ref>It may also react with [[amine]]s to create a 1,2,3-benzothiadiazoles derivative.<ref name=":1" />The fluoro-,chloro-,bromo- and iodo- 1,2,3-Benzothiadiazoles are used / found in electrophilic solutions.<ref>{{Cite journal|last1=Ward|first1=E. R.|last2=Heard|first2=D. D.|date=1965-01-01|title=183. 1,2,3-Benzothiadiazole. Part III. Electrophilic substitution in 5- and 7-amino-1,2,3-benzothiadiazoles and the preparation of some substituted 1,2,3-benzothiadiazoles|url=https://pubs.rsc.org/en/content/articlelanding/1965/jr/jr9650001023|journal=Journal of the Chemical Society (Resumed)|language=en|pages=1023–1028|doi=10.1039/JR9650001023|issn=0368-1769}}</ref>
<ref name=":1">{{Cite journal|last2=Poesche|first2=W. H.|last3=Higgins|first3=D.|last4=Heard|first4=D. D.|title=458. 1,2,3-Benzothiadiazole. Part I. Nitro-, amino-, and hydroxy-derivatives|url=https://pubs.rsc.org/en/content/articlelanding/1962/jr/jr9620002374|journal=Journal of the Chemical Society (Resumed)|year=1962|language=en|volume=|pages=2374–2379|doi=10.1039/JR9620002374|issn=0368-1769|via=|last1=Ward|first1=E. R.}}</ref>It may also react with [[amine]]s to create a 1,2,3-benzothiadiazoles derivative.<ref name=":1" />
Some of 1,2,3-Benzothiadiazole derivatives are either [[Pesticides]] or [[Herbicides]].<ref name=":2" /><ref>{{Cite web|last=Google|first=Patents|date=|title=US3536728A-1,2,3-Benzothiadiazole|url=https://www.patents.google.com/patents/US3536728A/en|url-status=live|archive-url=|archive-date=|access-date=|website=}}</ref>1,2,3-Benzothiadiazole has many more reactions and their derivatives, some of the most common ones being [[1,2,3-Benzothiadiazole-7-carboxylic acid]] and [[Acibenzolar-S-methyl]].
Some of 1,2,3-Benzothiadiazole derivatives are either [[Pesticides]] or [[Herbicides]].<ref name=":2" /><ref>{{Cite web|last=Google|first=Patents|date=|title=US3536728A-1,2,3-Benzothiadiazole|url=https://www.patents.google.com/patents/US3536728A/en|url-status=live|archive-url=|archive-date=|access-date=|website=}}</ref>1,2,3-Benzothiadiazole has many more reactions and their derivatives, some of the most common ones being [[1,2,3-Benzothiadiazole-7-carboxylic acid]] and [[Acibenzolar-S-methyl]].


Revision as of 17:16, 18 September 2020

1,2,3-Benzothiadiazole
Names
IUPAC name
1,2,3-Benzothiadiazole
Systematic IUPAC name
1,2,3-Benzothiadiazole
Other names
  • Benzothiadiazole
  • Benzthiadiazole
  • Azabenzothiadiazole
  • benzo-1,2,3-thiadiazole
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 205-989-4
MeSH benzo-1,2,3-thiadiazole
  • InChI=1S/C6H4N2S/c1-2-4-6-5(3-1)7-8-9-6/h1-4H
    Key: FNQJDLTXOVEEFB-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)N=NS2
Properties
C6H4N2S
Molar mass 136.17 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,2,3-Benzothiadiazole is an aromatic heterocyclic[1] organic compound which belongs to the benzothiadiazole category. It has a chemical formula of C6H4N2S.It consists of a benzene ring and a Thiadiazole.

It is a part of the compound acibenzolar-S-methyl, a pesticide.[2]

Reactions

[3]It may also react with amines to create a 1,2,3-benzothiadiazoles derivative.[3] Some of 1,2,3-Benzothiadiazole derivatives are either Pesticides or Herbicides.[2][4]1,2,3-Benzothiadiazole has many more reactions and their derivatives, some of the most common ones being 1,2,3-Benzothiadiazole-7-carboxylic acid and Acibenzolar-S-methyl.

Production.

1,2,3-Benzothiadiazole is readily prepared by the diazotisation reaction of 2-aminothiophenol with sodium nitrite. The Chemistry of this heterocycle and its simple derivatives have been reviewed.[5]

History

1,2,3-Benzothiadiazole has been known since 1888.[6][7]

References

  1. ^ "Search Results - Access Structures". doi:10.5517/cc9618s. {{cite journal}}: Cite journal requires |journal= (help)
  2. ^ a b [1], "Pesticidal compositions comprising 1,2,3-benzothiadiazole derivatives", issued 1999-07-28 
  3. ^ a b Ward, E. R.; Poesche, W. H.; Higgins, D.; Heard, D. D. (1962). "458. 1,2,3-Benzothiadiazole. Part I. Nitro-, amino-, and hydroxy-derivatives". Journal of the Chemical Society (Resumed): 2374–2379. doi:10.1039/JR9620002374. ISSN 0368-1769.
  4. ^ Google, Patents. "US3536728A-1,2,3-Benzothiadiazole". {{cite web}}: |last= has generic name (help)CS1 maint: url-status (link)
  5. ^ "1,2,3-Benzothiadiazole". Houben-Weyl Methods of Organic Chemistry Vol. E 8d, 4th Edition Supplement: Hetarenes III (Five-Membered Rings with Two and More Heteroatoms in the Ring System) - Part 4. 14 May 2014. pp. 93–104. ISBN 9783131812445.
  6. ^ Storr, R. C.; Gilchrist, T. L., eds. (2004). "Product Class 9: 1,2,3-Thiadiazoles". Science of Synthesis. Vol. 13: Category 2, Hetarenes and Related Ring Systems. doi:10.1055/sos-SD-013-00386. ISBN 9783131122810.
  7. ^ "1,2,3-Thiadiazoles and their Benzo derivatives".{{cite web}}: CS1 maint: url-status (link)
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