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1,2,3-Benzothiadiazole

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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

1,2,3-Benzothiadiazole reacts with Fluorine,Chlorine,Bromine and Iodine to form their own respective 1,2,3-Benzothiadiazoles.[3]It may also react with Nitrogen and Amine to create their own respective 1,2,3-Benzothiadiazoles.[3]The fluoro-,chloro-,bromo- and iodo- 1,2,3-Benzothiadiazoles are used / found in electrophilic solutions.[4] Some of 1,2,3-Benzothiadiazole derivatives are either Pesticides or Herbicides.[2][5]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.[6]

History

1,2,3-Benzothiadiazole has been known since 1888.[7][8]

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. ^ Ward, E. R.; Heard, D. D. (1965-01-01). "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". Journal of the Chemical Society (Resumed): 1023–1028. doi:10.1039/JR9650001023. ISSN 0368-1769.
  5. ^ Google, Patents. "US3536728A-1,2,3-Benzothiadiazole". {{cite web}}: |last= has generic name (help)CS1 maint: url-status (link)
  6. ^ "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.
  7. ^ 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.
  8. ^ "1,2,3-Thiadiazoles and their Benzo derivatives".{{cite web}}: CS1 maint: url-status (link)
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