2-Amino-6-methoxybenzothiazole Chemical Properties

Melting point:

165-167 °C (lit.)

Boiling point:

240°C

Density 

1.2425 (rough estimate)

refractive index 

1.5690 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

very slightly in Methanol

pka

pK1: 4.50(+1) (25°C)

form 

Crystalline Powder

color 

White to beige

Water Solubility 

<0.1 g/100 mL at 21 ºC

Stability:

Stable, but may be light sensitive. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C8H8N2OS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3,(H2,9,10)

InChIKey

KZHGPDSVHSDCMX-UHFFFAOYSA-N

SMILES

S1C2=CC(OC)=CC=C2N=C1N

CAS DataBase Reference

1747-60-0(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-6-methoxybenzothiazole (1747-60-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

RTECS 

DL2100000

TSCA 

Yes

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29342080

Toxicity

mouse,LD50,intravenous,140mg/kg (140mg/kg),Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 486, 1952.

MSDS

• Language:English Provider:6-Methoxy-2-aminobenzothiazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-6-methoxybenzothiazole Usage And Synthesis

Uses

2-Amino-6-methoxybenzothiazole is an intermediate used to prepare novel series of Schiff bases and 4-thiazolidinones. It is also used in the synthesis of 2-cyano-6-methoxybenzothiazole.

Chemical Properties

off-white to tan-coloured powder

Uses

2-Amino-6-methoxybenzothiazole was used as building block in the syntheses of novel series of Schiff bases and 4-thiazolidinones. It was used in the synthesis of 2-cyano-6-methoxybenzothiazole, key intermediate for the synthesis of firefly luciferin.

General Description

Fine off-white to light tan powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Amino-6-methoxybenzothiazole may be sensitive to exposure to light. 2-Amino-6-methoxybenzothiazole is incompatible with strong oxidizers.

Fire Hazard

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

Synthesis

0.1 mole of p-aminoanisole and 0.1 mole of potassium thiocyanate (KCNS) were dissolved in 100 mL of glacial acetic acid (AcOH) and the mixture was cooled and stirred in an ice bath for 10-20 minutes. Subsequently, 0.1 mol of bromine in glacial acetic acid solution was slowly added dropwise, with the rate of dropwise acceleration controlled to maintain the reaction temperature below 10 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 2-4 hours. After completion of the reaction, the resulting hydrobromide (HBr) salt was separated by filtration, washed with glacial acetic acid and dried. The dried salt was dissolved in hot water and alkalized by adjusting the pH to 11.0 with ammonia solution (NH4OH). The precipitate precipitated was filtered, washed with water and dried to give the target product 2-amino-6-methoxybenzothiazole. The reaction process was monitored by thin layer chromatography (TLC) using toluene: acetone (8:2) as unfolding agent.

References

[1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[2] Synlett, 2009, # 16, p. 2682 - 2684
[3] Heterocyclic Communications, 2018, vol. 24, # 5, p. 255 - 258
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 5, p. 1124 - 1133
[5] European Journal of Medicinal Chemistry, 2008, vol. 43, # 5, p. 1114 - 1122

2-Amino-6-methoxybenzothiazole(1747-60-0)Related Product Information

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• Basic Blue 54