2-Aminobenzothiazole

2-Aminobenzothiazole
Names
	Other names 2-aminobenzthiazole
Identifiers
CAS Number	136-95-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:167751;
ChEMBL	ChEMBL329785;
ChemSpider	8382;
ECHA InfoCard	100.004.790
EC Number	205-268-4;
PubChem CID	8706;
UNII	08K5TLY3EQ;
UN number	2811 (2-AMINOBENZOTHIAZOLE)
CompTox Dashboard (EPA)	DTXSID1024467 ;
	InChI InChI=1S/C7H6N2S/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H,(H2,8,9) Key: UHGULLIUJBCTEF-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)N=C(S2)N;
Properties
Chemical formula	C7H6N2S
Molar mass	150.20 g·mol−1
Density	1.753 g/cm3
Melting point	126–129 °C (259–264 °F; 399–402 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H319, H400
Precautionary statements	P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Aminobenzothiazole is the organic compound with the formula C₆H₄S(N)CNH₂. It is related to the parent benzothiazole, but with an amino group at the unique methyne position on the thiazole ring. As confirmed by X-ray crystallography, it is a planar molecule, which exists as the amine tautomer.^[1]

2-Aminobenzothiazoles are often prepared by cyclization of 2-bromo-substituted arylthioureas.^[2]

BrC₆H₄NHC(S)NH₂ → C₆H₄SNCNH₂ + HBr

Isothiocyanic acid, which can be generated in situ from sodium thiocyanate, adds to anilines to also afford 2-aminobenzothiazoles.^[3] Many other methods are available.^[4]

Diazotization of 2-aminobenzothiazoles gives diazonium salts. These salts undergo azo coupling with anilines. In this way some are prepared some useful dyes such as Basic Blue 54.^[5]

References

^ ^a ^b Altaf, Muhammad; Stoeckli-Evans, Helen (2009). "1,3-Benzothiazol-2-amine". Acta Crystallographica Section E: Structure Reports Online. 65 (8): o1894. Bibcode:2009AcCrE..65o1894A. doi:10.1107/S1600536809027561. PMC 2977242. PMID 21583584.
^ Ding, Qiuping; He, Xiaodan; Wu, Jie (2009). "Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate". Journal of Combinatorial Chemistry. 11 (4): 587–591. doi:10.1021/cc900027c. PMID 19449803.
^ Allen, C. F. H.; VanAllan, J. (1942). "2-Amino-6-Methylbenzothiazole". Organic Syntheses. 22: 16. doi:10.15227/orgsyn.022.0016{{cite journal}}: CS1 maint: multiple names: authors list (link).
^ Prajapati, Neelam P.; Vekariya, Rajesh H.; Borad, Mayuri A.; Patel, Hitesh D. (2014). "Recent Advances in the Synthesis of 2-Substituted Benzothiazoles: A Review". RSC Adv. 4 (104): 60176–60208. Bibcode:2014RSCAd...460176P. doi:10.1039/C4RA07437H.
^ Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_487.pub2. ISBN 978-3-527-30385-4.

[XRD-1] Altaf, Muhammad; Stoeckli-Evans, Helen (2009). "1,3-Benzothiazol-2-amine". Acta Crystallographica Section E: Structure Reports Online. 65 (8): o1894. Bibcode:2009AcCrE..65o1894A. doi:10.1107/S1600536809027561. PMC 2977242. PMID 21583584.

[2] Ding, Qiuping; He, Xiaodan; Wu, Jie (2009). "Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate". Journal of Combinatorial Chemistry. 11 (4): 587–591. doi:10.1021/cc900027c. PMID 19449803.

[3] Allen, C. F. H.; VanAllan, J. (1942). "2-Amino-6-Methylbenzothiazole". Organic Syntheses. 22: 16. doi:10.15227/orgsyn.022.0016{{cite journal}}: CS1 maint: multiple names: authors list (link).

[4] Prajapati, Neelam P.; Vekariya, Rajesh H.; Borad, Mayuri A.; Patel, Hitesh D. (2014). "Recent Advances in the Synthesis of 2-Substituted Benzothiazoles: A Review". RSC Adv. 4 (104): 60176–60208. Bibcode:2014RSCAd...460176P. doi:10.1039/C4RA07437H.

[5] Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_487.pub2. ISBN 978-3-527-30385-4.

[1]

[2]

[3]

[4]

[5]