5,6-Dichloro-2-benzothiazolamine Chemical Properties

Melting point:

175-180°C

Boiling point:

379.7±45.0 °C(Predicted)

Density 

1.654±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.79±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Water Solubility 

<0.1 g/100 mL at 17 ºC

CAS DataBase Reference

24072-75-1(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-5,6-dichlorobenzothiazole (24072-75-1)

Safety Information

Safety Statements 

24/25

HS Code 

29342000

MSDS

• Language:English Provider:5,6-Dichloro-2-benzothiazolamine

5,6-Dichloro-2-benzothiazolamine Usage And Synthesis

Chemical Properties

White powder

General Description

White solid or powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated organosulfide and an amine. 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.

Fire Hazard

Flash point data for 5,6-Dichloro-2-benzothiazolamine are not available. 5,6-Dichloro-2-benzothiazolamine is probably combustible.

Synthesis

To a solution of acetic acid (160 mL) containing 3,4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol), a solution of acetic acid (160 mL) with liquid bromine (31 g, 0.19 mol) was slowly added at 0 °C, while stirring was maintained. The reaction temperature was maintained at 0 °C throughout the addition. After addition, the reaction mixture was continued to be stirred at 0 °C for 2 h, and then warmed up to 15 °C for 14 h. The reaction temperature was kept constant at 0 °C for 2 h. The reaction temperature was kept constant at 15 °C for 2 h. Upon completion of the reaction, the reaction solution was diluted with water (100 mL), the pH was adjusted to 7-8 with ammonium hydroxide, and then extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with brine (3 x 300 mL) and subsequently concentrated under reduced pressure. The crude product was purified by preparative HPLC [Apparatus: GX-B; Column: GEMINI 250 × 50 mm, particle size: 10 μm; Mobile phase: 25-50% acetonitrile in water (containing 0.1% TFA, v/v)] to afford the target compound 5,6-dichlorobenzo[d]thiazol-2-amine (2.6 g, 19% yield) as a white solid.LCMS ( ESI): tR = 0.694min, m/z (M+H)+ 219.0. 1H-NMR (CD3OD, 400MHz): δ 7.89 (s, 1H), 7.55 (s, 1H).

References

[1] Patent: WO2017/69980, 2017, A1. Location in patent: Paragraph 00319; 00320
[2] Bioorganic Chemistry, 2016, vol. 67, p. 130 - 138

5,6-Dichloro-2-benzothiazolamine (24072-75-1)Related Product Information

• 2-Benzothiazolamine
• 2-Amino-6-chlorobenzothiazole
• 2,2'-Dithiobis(benzothiazole)
• EC 2.6.1.2
• Benzothiazole
• Glucosamine
• 2-Aminothiazole
• ALTRENOGEST
• 3-Aminophenol
• Acetaminophen
• 6-Aminocaproic acid
• 2-Mercaptobenzothiazole
• Glycine
• Dichloroethane
• Tris(hydroxymethyl)aminomethane
• 2-AMINO-5,6-DICHLOROBENZOTHIAZOLE
• 2-AMINO-4,6-DICHLOROBENZOTHIAZOLE
• 6-CHLOROBENZOTHIAZOLE