2941-58-4

Basic information

• Product Name: 2-Bromo-6-methoxybenzothiazole
• Synonyms: 2-BROMO-6-METHOXYBENZOTHIAZOLE;Benzothiazole, 2-bromo-6-methoxy-;2-bromo-6-methoxybenzo[d]thiazole
• CAS NO: 2941-58-4
• Molecular Formula: C₈H₆BrNOS
• Molecular Weight: 244.11
• Product Categories: Thiazole
• Mol File: 2941-58-4.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 335.399oC at 760 mmHg
• Flash Point: 156.644oC
• Appearance: /
• Density: 1.667g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.53±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-6-methoxybenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-methoxybenzothiazole(2941-58-4)
• EPA Substance Registry System: 2-Bromo-6-methoxybenzothiazole(2941-58-4)

Safety Data

• Hazardous Substances Data: 2941-58-4(Hazardous Substances Data)

Usage

Uses

2-Bromo-6-methoxybenzothiazole is used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

2-Bromo-6-methoxybenzo[d]thiazole (B2) (Scheme 1). 6- Methoxybenzo[d]thiazol-2-amine (5.0 g; 27.7 mmol) was dissolved in 125 mL CHBCN. t- Butylnitrite (3.4 mL; 28 mmol) was added slowly. CuBr (5.0 g; 34.9 mmol) was added portion-wise through a funnel. The reaction was monitored by HPLC. After 3 hours, ethyl acetate (500 mL) was added, and the mixture was filtered through celite. The organic layer was washed with brine twice (200 mL each). The organic layer was dried over MgSO4. After filtration, the solvent was removed. The residual was dissolved in 50 mL CH2Cl2, and 2 g of silica gel was added. After drying, the silica gel loaded on a silica gel cake in hexane. The product was eluted with 5% ethyl acetate and 95% hexane. A yellowish band was collected (1.5 L). The solvent was removed to afford the product. Yield: 0.81 g 12%.

InChI:InChI=1/C8H6BrNOS/c1-11-5-2-3-6-7(4-5)12-8(9)10-6/h2-4H,1H3

Upstream product

• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 110-46-3 isopentyl nitrite 
• 7787-70-4 copper(I) bromide 

Downstream Products

• 808755-67-1 6-hydroxy-2-bromo-benzothiazole 
• 1042131-26-9 [4-(4-isopropyl-phenyl)-6-propargyloxy-quinazolin-2-yl]-(6-methoxy-benzothiazol-2-yl)-methanone 
• 953771-25-0 (1R,2R)-2-((6-methoxybenzo[d]thiazol-2-yl)amino)cyclohexan-1-ol 
• 953771-28-3 2-(((1R,2R)-2-hydroxycyclohexyl)amino)benzo[d]thiazol-6-ol 
• 945400-92-0 2-bromo-6-(tert-butyldimethylsilyloxy)benzo[d]thiazole 

Relevant articles and documents

alpha-SYNUCLEIN AGGREGATE BINDING AGENT AND IMAGING METHOD

The present invention provides an α-synuclein aggregate binding agent that has high binding selectivity for an α-synuclein aggregate. The α-synuclein aggregate binding agent contains a compound represented by a formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof: in the formula (I), R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl; R3 is hydrogen or halogen; the ring A is a benzene or pyridine ring; the ring B is represented by the following formula (i) or (ii): R4 and R5 are each independently selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl.

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties

Five new firefly luciferin (1) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains (2–4) and heterocyclic rings derived from amino acids (5 and 6) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin (6), possessing a pyrroline-substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP-carboluciferin (AMP=adenosine monophosphate) and AMP-firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower.