2-HYDRAZINOBENZOTHIAZOLE Chemical Properties

Melting point:

198-202 °C (lit.)

Boiling point:

352.4±25.0 °C(Predicted)

Density 

1.2404 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Solubility in hot methanol almost transparent.

pka

2.81±0.20(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H7N3S/c8-10-7-9-5-3-1-2-4-6(5)11-7/h1-4H,8H2,(H,9,10)

InChIKey

JYSUYJCLUODSLN-UHFFFAOYSA-N

SMILES

S1C2=CC=CC=C2N=C1NN

CAS DataBase Reference

615-21-4(CAS DataBase Reference)

EPA Substance Registry System

2(3H)-Benzothiazolone, hydrazone (615-21-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38

Safety Statements 

26-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DL4725000

TSCA 

Yes

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29342000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-HYDRAZINOBENZOTHIAZOLE Usage And Synthesis

Chemical Properties

slightly yellow to beige-green crystalline powder

Uses

It is employed in the spectrophotometric analysis determination of methenamine and its salts. It is also used in the detection and repair mechanism of Etheno-DNA adducts.

Synthesis

General procedure for the synthesis of 2-hydrazinobenzothiazole from 2-aminobenzothiazole: Hydrazine hydrate (1 equiv.) was dissolved in ethylene glycol at 5 °C. Under stirring, concentrated hydrochloric acid (2 mL) was added slowly and dropwise, followed by 2-aminobenzothiazole (1 eq.). The reaction mixture was heated to reflux for 2-3 hours, after which it was cooled to room temperature. Upon completion of the reaction, the solid product formed was collected by filtration, washed with water and purified by recrystallization from ethanol to afford the target compound 2-hydrazinobenzo[d]thiazole (32). The product was white crystals in 90% yield with a melting point ranging from 200 °C to 202 °C. 1H NMR (DMSO-d6, 400 MHz) data were as follows: δ 4.84 (2H, s), 6.85-7.65 (4H, m), 8.62 (1H, s). ESI-MS (m/z) analysis showed the molecular ion peak as 166 (MH+).

References

[1] Helvetica Chimica Acta, 1980, vol. 63, # 3, p. 682 - 692
[2] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 418 - 428
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[4] Medicinal Chemistry Research, 2012, vol. 21, # 9, p. 2428 - 2442
[5] Journal of Molecular Structure, 2014, vol. 1060, # 1, p. 215 - 222

2-HYDRAZINOBENZOTHIAZOLE(615-21-4)Related Product Information

• 1-(6-CHLORO-1,3-BENZOTHIAZOL-2-YL)HYDRAZINE
• 2-HYDRAZINOBENZOTHIAZOLE
• ACETONE-BENZOTHIAZOLYL-2-HYDRAZONE
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• 6-BROMO-2-HYDRAZINO-1,3-BENZOTHIAZOLE
• HYDRAZINE
• (6-NITROBENZOTHIAZOL-2-YL)-HYDRAZINE
• 3-[1-(1,3-benzothiazol-2-yl)hydrazino]propanenitrile
• ETHYL 4-AZA-4-(BENZOTHIAZOL-2-YLAMINO)-3-(TRIFLUOROMETHYL)BUT-3-ENOATE
• AURORA 12505
• BUTTPARK 137\40-05
• PRINCETON PBMR000200
• 5-CHLORO-2-HYDRAZINO-1,3-BENZOTHIAZOLE
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• BUTTPARK 137\40-03
• BUTTPARK 137\40-57
• 3-{5-[(E)-(1,3-BENZOTHIAZOL-2-YLHYDRAZONO)METHYL]-2-FURYL}BENZOIC ACID
• AURORA 2430