2-Amino-6-nitrobenzothiazole

2-Amino-6-nitrobenzothiazole Property

Melting point:

247-249 °C (lit.)

Boiling point:

411.7±37.0 °C(Predicted)

Density 

1.4666 (rough estimate)

refractive index 

1.6740 (estimate)

storage temp. 

2-8°C, protect from light

pka

1.76±0.10(Predicted)

Appearance

Light yellow to green yellow Solid

CAS DataBase Reference

6285-57-0(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-6-nitrobenzothiazole (6285-57-0)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

2

RTECS 

DL0865000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29342080

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Amino-6-nitrobenzothiazole Chemical Properties,Usage,Production

Chemical Properties

yellow crystalline powder

Uses

2-Amino-6-nitrobenzothiazole has been used:

• as model analyte for voltammetric determination of electrochemically reducible organic substances
• in the synthesis of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide derivatives
• in the preparation of push-pull nonlinear optical chromophores containing thiazole and benzothiazole acceptors
• as a base in dye production by diazotation reaction

General Description

Orange crystals or yellow powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Amino-6-nitrobenzothiazole is incompatible with strong oxidizing agents and strong acids.

Fire Hazard

Flash point data for 2-Amino-6-nitrobenzothiazole are not available; however, 2-Amino-6-nitrobenzothiazole is probably combustible.

Synthesis

GENERAL METHOD: A solution of 4-nitroaniline (2 mmol) in acetonitrile (15 ml) was slowly added to a solution of potassium thiocyanate (8 mmol) in acetonitrile (15 ml). Subsequently, 0.06 g (30 mol%) of BF3/SiO2 nanocatalyst was added to the reaction system and the mixture was placed in an ice salt bath and mechanically stirred for 30 min. A solution of bromine (4 mmol, 0.2 ml) in acetonitrile (3 ml) was slowly added through a dropping funnel, and the dropping rate was controlled to ensure that the reaction temperature did not exceed 0 °C. After the addition of the bromine solution, the reaction continued to be stirred at room temperature for 4 h, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, the reaction mixture was poured into water, heated in a 70 °C water bath and thermally filtered to remove the catalyst. The catalyst was washed with acetone and recycled for reuse. The filtrate was neutralized to neutrality with 10% NaOH solution and the precipitated solid was collected by filtration, dried and recrystallized with ethanol (10 ml) to give the target product 2-amino-6-nitrobenzothiazole. The structure of the product was confirmed by the following physical and spectral data and verified by comparison with standards. Spectral data of 2-amino-6-nitrobenzothiazole: yellow solid; yield = 93%; melting point = 202-204 °C (literature value 203 °C); FT-IR (KBr, cm^-1): 3315, 3012, 2835, 1580, 1476, 1261, 920, 742, 512; ^1H NMR (400 MHz, CDCl3 , δ ppm): 5.44 (s, 2H, NH2), 7.4-7.5 (d, 2H, Ar-H), 7.71 (s, 1H, Ar-H); ^13C NMR (100 MHz, DMSO-d6, δ ppm): 119, 120.9, 125.15, 126.07, 133.1, 152.15, 167.75.

References

[1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[2] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 7855 - 7868
[3] European Journal of Medicinal Chemistry, 2008, vol. 43, # 5, p. 1114 - 1122
[4] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 41 - 51
[5] Russian Journal of Applied Chemistry, 2015, vol. 88, # 12, p. 2065 - 2073