68867-20-9

Basic information

• Product Name: 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90
• Synonyms: 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90;6-IODO-2-METHYL-1,3-BENZOTHIAZOLE;6-Iodo-2-methyl-1,3-benzothiazole 90%;6-Iodo-2-methylbenzothiazole;6-IODO-2-METHYL-1,3-BENZOTHIAZOLE(WXG02695)
• CAS NO: 68867-20-9
• Molecular Formula: C₈H₆INS
• Molecular Weight: 275.10941
• Mol File: 68867-20-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 134 °C
• Boiling Point: 323.4°C at 760 mmHg
• Flash Point: 149.4°C
• Appearance: /
• Density: 1.902g/cm³
• Vapor Pressure: 0.000495mmHg at 25°C
• Refractive Index: 1.739
• CAS DataBase Reference: 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90(CAS DataBase Reference)
• NIST Chemistry Reference: 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90(68867-20-9)
• EPA Substance Registry System: 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90(68867-20-9)

Safety Data

• Hazardous Substances Data: 68867-20-9(Hazardous Substances Data)

Usage

General Description

6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90 is a chemical compound characterized by the presence of an iodo group, a methyl group, and a benzothiazole ring. 6-IODO-2-METHYL-1,3-BENZOTHIAZOLE 90 is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes. It is a versatile building block in organic chemistry due to its ability to participate in a variety of reactions, including Suzuki coupling, Sonogashira coupling, and nucleophilic substitution. Additionally, it is known for its mild odor and can be harmful if ingested or inhaled, so proper safety precautions should be taken when handling this substance.

InChI:InChI=1/C8H6INS/c1-5-10-7-3-2-6(9)4-8(7)11-5/h2-4H,1H3

Upstream product

• 533-70-0 2,4-diiodoaniline 
• 861613-82-3 N-(2-iodo-4-iodophenyl)acetamide 
• 120-75-2 2-Methylbenzothiazole 
• 540-37-4 p-aminoiodobenzene 
• 62-53-3 aniline 
• 2941-62-0 6-amino-2-methylbenzothiazole 
• 20980-01-2 N-(4-iodophenyl)thioacetamide 
• 622-50-4 4-Acetamido-1-iodobenzene 
• 2941-63-1 2-methyl-6-nitrobenzothiazole 

Downstream Products

• 1223510-99-3 (E)-6-[4-(N,N-dimethylamino)phenylethenyl]-2-methylbenzothiazole 
• 1223511-01-0 (E)-6-[4-(N,N-diphenylamino)phenylethenyl]-2-methylbenzothiazole 
• 1338574-35-8 6-[(4-diphenylaminophenyl)ethyn-1-yl]benzothiazole-2-carbaldehyde 
• 1338574-38-1 2-{{6-[(4-diphenylaminophenyl)ethyn-1-yl]benzothiazol-2-yl}methylene}malononitrile 
• 103983-99-9 3-(2-methyl-benzothiazol-6-yl)-acrylonitrile 
• 1613640-02-0 2-(4-methoxybenzyl)-5-(2-methylbenzo[d]thiazol-6-yl)isothiazolidine 1,1-dioxide 

Relevant articles and documents

Direct iodination of electron-deficient benzothiazoles: Rapid access to two-photon absorbing fluorophores with quadrupolar D-π-A-π-D architecture and tunable heteroaromatic core

Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1-2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected bu

Structure-Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimers Disease Brains

In order to explore novel tau-imaging agents that can selectively detect neurofibrillary tangles in Alzheimers disease (AD) brains, we designed and synthesized a series of heterocyclic phenylethenyl and (3-pyridinyl)ethenyl derivatives with or without a dimethyl amino group. In in vitro autoradiography using AD brain sections, all radioiodinated ligands with a dimethyl amino group bound to Aβ deposits in the sections. In contrast, the ligands without a dimethyl amino group showed different patterns of radioactivity accumulation in the sections depending on the kind of heterocycle contained in their molecules. Particularly, a phenylethenyl benzimidazole derivative ([125I]64) showed marked radioactivity accumulation in the temporal lobe which corresponded with the distribution of tau deposits. [125I]64 also showed the most favorable pharmacokinetics in normal mouse brains (3.69 and 0.06% ID/g at 2 and 60 min postinjection, respectively) among all ligands in this study. Taken together, these results suggest that [123I]64 may be a new candidate tau-imaging agent.

Synthesis and characterization of near-infrared absorbing water soluble squaraines and study of their photodynamic effects in DLA live cells

Here, we report the synthesis, photophysical properties and photodynamic effects in DLA live cells of three water soluble squaraine dyes, viz. bisbenzothiazolium squaraine dyes SQMI and SQDI with iodine in one and both benzothiazolium units, respectively, and an unsymmetrical squaraine dye ASQI containing iodinated benzothiazolium and aniline substituents. The diiodinated SQDI showed an anomalous trend in both fluorescence and triplet quantum yields over the monoiodinated SQMI, with SQDI showing higher fluorescence and lower triplet quantum yields compared to SQMI. Nanosecond laser flash photolysis of SQDI and SQMI indicated the formation of triplet excited states with quantum yield of 0.19 and 0.26, respectively. On photoirradiation, both the SQDI and SQMI generate singlet oxygen and it was observed that both dyes undergoing oxidation reactions with the singlet oxygen generated. ASQI which exhibited a lower triplet quantum yield of 0.06 was, however, stable and did not react with the singlet oxygen generated. In vitro cytotoxicity studies of these dyes in DLA live cells were performed using Trypan blue dye exclusion method and it reflect an order of cytotoxicity of SQDI>SQMI>ASQI. Intracellular generation of the ROS was confirmed by dichlorofluorescein assay after the in vitro PDT. Synthesis, photophysical properties and photodynamic effects in DLA live cells of three water soluble squaraine dyes, SQDI, SQMI and ASQI, are presented. On photoirradiation, both the SQDI and SQMI generate singlet oxygen where both the dyes undergoing oxidation reactions with the singlet oxygen generated, whereas ASQI was stable and did not react with the singlet oxygen. In vitro cytotoxicity studies of these dyes in DLA cells were performed using Trypan blue dye exclusion method and intracellular generation of ROS was confirmed using dichlorofluorescein assay after the in vitro PDT.