4-Methoxy-2-aminobenzothiazole Chemical Properties

Melting point:

153-155 °C (lit.)

Boiling point:

240°C (rough estimate)

Density 

1.2425 (rough estimate)

refractive index 

1.5690 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline Powder

pka

4.09±0.10(Predicted)

color 

Beige

Water Solubility 

<0.1 g/100 mL at 19.5 ºC

BRN 

141363

InChI

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

InChIKey

YEBCRAVYUWNFQT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5464-79-9(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-4-methoxybenzothiazole (5464-79-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22

Safety Statements 

36

WGK Germany 

3

RTECS 

DL2000000

Hazard Note 

Harmful

HS Code 

29342000

MSDS

• Language:English Provider:2-Amino-4-methoxybenzothiazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Methoxy-2-aminobenzothiazole Usage And Synthesis

Chemical Properties

Beige crystalline powder

Uses

2-Amino-4-methoxybenzothiazole is a useful research intermediate for the synthesis of various benzothiazole and aminobenzothiazoles derivatives with antibacterial and antifungal activity.

General Description

Beige chunky solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 4-Methoxy-2-aminobenzothiazole emits very toxic fumes of NOx and SOx.

Fire Hazard

Flash point data for 4-Methoxy-2-aminobenzothiazole are not available. 4-Methoxy-2-aminobenzothiazole is probably combustible.

Biochem/physiol Actions

2-Amino-4-methoxybenzothiazole on condensation reaction with 4-acetamidobenzaldehyde affords tridentate Schiff bases. It reacts with 2,4,6-trichloro 1,3,5-triazine to give 2-(4-methoxybenzothiazol-2′-ylamino)-4-(phenylthioureido)-6-(substitutedthioureido)-1,3,5-triazines.

Synthesis

General procedure for the synthesis of 2-amino-4-methoxybenzothiazole from 1-(2-methoxyphenyl)thiourea: 1-(2-methoxyphenyl)thiourea (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To this solution, lithium bromide (2.6 g, 0.03 mol) was added at room temperature, followed by slow dropwise addition of bromine (1 ml, 0.02 mol) under ice bath conditions. The reaction mixture was heated to 40°C and the reaction was stirred at this temperature for 17 hours. After completion of the reaction, the system was cooled to room temperature and allowed to stand for 2 hours. The reaction product was collected by filtration and washed with acetic acid. Finally, the resulting white solid was dried in a vacuum oven to afford the target product 2-amino-4-methoxybenzothiazole (3.5 g, 94.08% yield).

References

[1] Patent: US2016/102066, 2016, A1. Location in patent: Paragraph 0021; 0025; 0027
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[4] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189
[5] Chem.Abstr., 1941, p. 452

4-Methoxy-2-aminobenzothiazole(5464-79-9)Related Product Information

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• ALTRENOGEST
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• 2-Benzothiazolamine
• Tris(hydroxymethyl)aminomethane
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• 2-Benzothiazolamine,4-ethoxy-(9CI)
• 2(3H)-Benzothiazolone,4-methoxy-,hydrazone(9CI)
• 2-Benzothiazolamine,4,7-dimethoxy-(9CI)