24072-75-1

Basic information

• Product Name: 5,6-Dichloro-2-benzothiazolamine
• 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-
• CAS NO: 24072-75-1
• Molecular Formula: C₇H₄Cl₂N₂S
• Molecular Weight: 219.09
• EINECS: 246-006-9
• Product Categories: Intermediates of Dyes and Pigments;BENZOTHIAZOLE
• Mol File: 24072-75-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 175-180°C
• Boiling Point: 379.7 °C at 760 mmHg
• Flash Point: 183.5 °C
• Appearance: White solid or powder
• Density: 1.654 g/cm³
• Vapor Pressure: 5.73E-06mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2.79±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 17℃
• CAS DataBase Reference: 5,6-Dichloro-2-benzothiazolamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dichloro-2-benzothiazolamine(24072-75-1)
• EPA Substance Registry System: 5,6-Dichloro-2-benzothiazolamine(24072-75-1)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 24072-75-1(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C7H4Cl2N2S/c8-3-1-2-4-6(5(3)9)12-7(10)11-4/h1-2H,(H2,10,11)

Upstream product

• 333-20-0 potassium thioacyanate 
• 95-76-1 m,p-dichloroaniline 
• 19250-09-0 3,4-dichlorophenylthiourea 
• 33240-95-8 3,4-dichloroaniline hydrochloride 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 6647-24-1 2-Amino-4,5-dichloro-benzenethiol 
• 875895-69-5 C₁₂H₈Cl₄N₂S₂ 
• 1316270-49-1 C₂₀H₁₁Cl₂N₇O₂S 
• 89642-32-0 2-bromo-5,6-dichlorobenzo[d]thiazole 
• 104495-87-6 C₂₁H₂₀Cl₂N₄O₄S 
• 1191403-91-4 C₁₆H₁₃Cl₂N₃O₃S₂ 
• 1233400-96-8 C₂₂H₁₇Cl₂N₃O₄S₂ 
• 1233400-95-7 C₂₁H₁₄Cl₃N₃O₃S₂ 
• 1233400-94-6 C₂₁H₁₅Cl₂N₃O₃S₂ 
• 1191404-00-8 C₁₄H₁₁Cl₂N₃O₂S₂ 
• 1268376-14-2 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-5,6-dichloro-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 100601-38-5 (2S,3S)-7,8-Dichloro-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 875895-76-4 2-(2-amino-4,5-dichloro-phenylsulfanylmethyl)-benzoic acid methyl ester 
• 875895-88-8 [2-(2-amino-4,5-dichloro-phenylsulfanylmethyl)-phenyl]-methanol 

Relevant articles and documents

Benzothiazole disperse dye monomer compound, synthesis method and application thereof

The invention discloses a benzothiazole disperse dye monomer compound. The structure of the compound is shown as formula (I) in the specification, wherein X1 and X4 are hydrogen, halogen, nitro, methyl or methoxy independently; X2 and X3 are independently hydrogen, halogen, nitro, methyl, methoxy or cyano; X5 is hydrogen or C1-C4 alkoxy; X6 is hydrogen, C1-C4 alkyl, NHCOR1 or halogen, and R1 is C1-C4 alkyl. The invention also discloses a preparation method of the benzothiazole disperse dye monomer compound and application thereof in preparation of disperse dyes. According to the invention, a phenylthiourea compound is adopted as the starting raw material, and by means of condensation ring closure, diazotization and coupling, a disperse dye filter cake can be obtained. The obtained dispersedye has bright color, high coloring intensity, good dyeing reproducibility, and has excellent promotion performance, dye uptake, dyeing fastness, sunlight resistance and sublimation fastness.

Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives

In the present study, 7-subsituted coumarin derivatives were synthesized using various aromatic and heterocyclic amines, and evaluated in vivo for anti-inflammatory and analgesic activity, and for ulcerogenic risk. The most active compounds were evaluated in vitro for 5-lipoxygenase (5-LOX) inhibition. Docking study was performed to predict the binding affinity, and orientation at the active site of the enzyme. In vivo anti-inflammatory and analgesic activity, and in vitro 5-LOX enzyme inhibition study revealed that compound 33 and 35 are the most potent compounds in all the screening methods. In vitro kinetic study of 35 showed mixed or non-competitive type of inhibition with 5-LOX enzyme. Presence of [Formula presented]3 group in 35 and [Formula presented] in 33 at C6-position of benzothiazole ring were found very important substitutions for potent activity.

Synthesis, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles

In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of ≤ 1 μM against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 μM), THP-1 (IC50 = 3 μM) and Caco-2 cell lines (IC50 = 9.9 μM), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation (radj2) obtained by leave-one-out technique.