1,2,3-Benzothiadiazole

Organic heterocyclic aromatic chemical 1,2,3-Benzothiadiazole 1,2,3-Benzothiadiazole.png Benzothiadiazole Benzthiadiazole Azabenzothiadiazole benzo-1,2,3-thiadiazole 1,2,3-Benzothiadiazole 67505 273-77-8 correct FDA R3PA3EL3RP 205-989-4 benzo-1,2,3-thiadiazole 60829 1S/C6H4N2S/c1-2-4-6-5(3-1)7-8-9-6/h1-4H FNQJDLTXOVEEFB-UHFFFAOYSA-N C1=CC=C2C(=C1)N=NS2 6 4 2 1 36-37 220.5 1.499 g/cm3 colorless solid 2,1,3-Benzothiadiazole 1,2,3-Benzothiadiazole is a bicyclic aromatic chemical composed of a benzene ring that is fused to a 1,2,3-thiadiazole. A colorless solid, the compound is soluble in organic solvents. Preparation 1,2,3-Benzothiadiazole is readily prepared by the diazotisation reaction of 2-aminothiophenol or its disulfide with sodium nitrite, as originally reported in 188710.1002/cber.188702001423 Zur Kenntniss der orthoamidirten aromatischen Mercaptane Jacobson J. Berichte der Deutschen Chemischen Gesellschaft 1887 20 1895–1903 and reviewed in several subsequent publications.10.1111/j.1478-4408.1948.tb02498.x A Review of the Chemistry of the Arylthiadiazoles or Internal Diazo–Sulphides Hodgson H.H. Dodoson D.P. Journal of the Society of Dyers and Colourists 1964 64 2 65–71 10.1016/B978-008096519-2.00092-8 1,2,3-Thiadiazoles and their Benzo Derivatives Comprehensive Heterocyclic Chemistry 1984 Thomas E.W. 447–462 9780080965192 Science of Synthesis 13: Category 2, Hetarenes and Related Ring Systems Storr R. C. Gilchrist T. L. 2004 10.1055/sos-SD-013-00386 Product Class 9: 1,2,3-Thiadiazoles 9783131122810 9783131812445 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 93–104 1,2,3-Benzothiadiazole Georg Thieme Verlag 400px By the Herz reaction anilines can be converted to benzothiadiazole. The method is attractive since less elaborate precursors (merely anilines) are required. Upon treatment with disulfur dichloride, the anilines give the intermediate 1,3,2-benzothiazathiolium salt, which is diazotised to complete the formation of a 1,2,3-benzothiadiazole. The parent system cannot be made this way, since the use of aniline in this reaction leads to formation of the 6-chloro derivative. Structure and bonding The molecule is planar. The N-N and S-N distances are respectively 128 and 171 picometers, indicative of multiple bond character.10.1016/0022-328X(91)86290-7 Transition metal heterocyclic chemistry: XI. Manganese cyclopentadienyldicarbonyl complexes of 1,2,3-selena- and thiadiazoles including structural comparison of free and complexed 1,2,3-benzothiadiazole and 4-phenyl-1,2,3-thiadiazole 1991 Mayr Armin J. Carrasco-Flores Benjamin Cervantes-Lee Francisco Pannell Keith H. Párkányi László Raghuveer Krishan Journal of Organometallic Chemistry 405 3 309–322 Like naphthalene, this heterocycle is a 10-electron system. Reactions 1,2,3-benzothiadiazole is much less nucleophilic than naphthalene. Nitration is slow.10.1039/JR9630004794 1,2,3-Benzothiadiazole. Part II. Electrophilic substitution in 4- and 6-amino-1,2,3-benzothiadiazoles 1963 Ward E. R. Heard D. D. Journal of the Chemical Society (Resumed) 4794–4803 For that reason, many of its simple derivatives have been made from 2-aminothiophenols already having additional substituents.10.1039/J39700002250 1,2,3-Benzothiadiazoles. Part I. A simplified synthesis of 1,2,3-benzothiadiazoles 1970 Kirby P. Soloway S. B. Davies J. H. Webb Shirley B. Journal of the Chemical Society C: Organic 16 2250 1,2,3-benzothiadiazole is a very weak base and alkylation reactions give exclusively the 3-amino quaternary salt.10.1039/J39700002060 1,2,3-Benzothiadiazole. Part VI. Investigations on the quaternisation of 1,2,3-benzothiadiazole and 1,2,3-benzoselenadiazole 1970 Jaffari G. A. Nunn A. J. Ralph J. T. Journal of the Chemical Society C: Organic 15 2060 Applications 1,2,3-benzothiadiazole has been claimed to synergise insecticides including dicrotophos10.1021/jf60170a011 Benzothiadiazoles, a novel group of insecticide synergists 1970 Felton John C. Jenner Donald W. Kirby Peter. Journal of Agricultural and Food Chemistry 18 4 671–673 but has not been commercialised for that application. The only derivative to have found significant use is the fungicide acibenzolar-S-methyl. References Category:Benzothiadiazoles