| Identification | More | [Name]
5,6-Dichloro-2-benzothiazolamine | [CAS]
24072-75-1 | [Synonyms]
5,6-dichloro-2-benzothiazolamin
5,6-dichlorobenzothiazol-2-amine
5,6-Dichlorobenzo[d]thiazol-2-amine
2-Benzothiazolamine,5,6-dichloro-(9CI)
2-AMINODICHLOROBENZOTHIAZOLE,98%
2-Amino-5,6-dichlorobenzothiazole
5,6-Dichloro-2-benzothiazolamine
2-Benzothiazolamine, 5,6-dichloro-
5,6-Dichloro-1,3-benzothiazol-2-amine | [EINECS(EC#)]
246-006-9 | [Molecular Formula]
C7H4Cl2N2S | [MDL Number]
MFCD00053558 | [Molecular Weight]
219.09 | [MOL File]
24072-75-1.mol |
| Hazard Information | Back Directory | [General Description]
White solid or powder. | [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. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available. 5,6-DICHLORO-2-BENZOTHIAZOLAMINE is probably combustible. | [Chemical Properties]
White powder | [Uses]
5,6-Dichloro-2-benzothiazolamine is used as an intermediate for disperse dyes and azo dyes. | [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 |
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J & K SCIENTIFIC LTD.
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https://www.jkchemical.com |
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