54346-87-1

Basic information

• Product Name: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE
• Synonyms: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE;5-METHOXY-BENZOTHIAZOL-2-YLAMINE;5-methoxybenzothiazol-2-amine;2-Benzothiazolamine,5-methoxy-(9CI);5-methoxybenzo[d]thiazol-2-amine;5-Methoxy-2-benzothiazolamine;2-Amino-5-methoxybenzothiazole;5-Methoxy-1,3-benzothiazole-2-amine
• CAS NO: 54346-87-1
• Molecular Formula: C8H8N2OS
• Molecular Weight: 180.23
• EINECS: 259-118-8
• Product Categories: BENZOTHIAZOLE;Amines;Thiazoles, Isothiazoles &Benzothiazoles;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 54346-87-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 154 °C
• Boiling Point: 347.5 °C at 760 mmHg
• Flash Point: 163.9 °C
• Appearance: /
• Density: 1.359 g/cm³
• Vapor Pressure: 5.38E-05mmHg at 25°C
• Refractive Index: 1.704
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.53±0.10(Predicted)
• CAS DataBase Reference: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(54346-87-1)
• EPA Substance Registry System: 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE(54346-87-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 54346-87-1(Hazardous Substances Data)

Usage

General Description

5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE is a chemical compound with the molecular formula C8H8N2OS. It is a benzothiazole derivative and contains a methoxy group attached to the benzene ring. 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE is commonly used in the pharmaceutical industry as a building block for the synthesis of various heterocyclic compounds with potential biological activities. Its structural features make it a valuable intermediate for the development of new drugs and biologically active molecules. The presence of the amino group also makes it useful for chemical reactions such as amidation, acylation, and condensation. Overall, 5-METHOXY-1,3-BENZOTHIAZOL-2-AMINE plays an important role in medicinal chemistry and drug discovery.

InChI:InChI=1/C8H8N2OS/c1-11-5-2-3-7-6(4-5)10-8(9)12-7/h2-4H,1H3,(H2,9,10)

Upstream product

• 37014-08-7 3-methoxyphenylthiourea 
• 3425-46-5 potassium selenocyanate 
• 2942-14-5 5-methoxy-1,3-benzothiazole 
• 333-20-0 potassium thioacyanate 
• 536-90-3 m-Anisidine 
• 27191-09-9 m-anisidine hydrochloride 

Downstream Products

• 118526-19-5 5-hydroxy-1,3-benzothiazol-2-amine 
• 2941-72-2 6-methoxy-2-methylbenzothiazole 
• 6274-29-9 2-amino-5-methoxy-thiophenol 
• 14482-32-7 2-amino-4-methoxybenzenethiol 
• 918154-63-9 3-(5-methoxy-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 343615-77-0 C₂₄H₂₉N₃O₅S₂ 
• 103040-91-1 N-(5-methoxybenzo[d]thiazol-2-yl)acetamide 
• 80945-74-0 2-hydrazinyl-5-methoxybenzo[d]thiazole 
• 36210-53-4 2-[(2-amino-4-methoxyphenyl)disulfanyl]-4-methoxyaniline 
• 19397-84-3 5-methoxy-2-(methylthio)aniline 
• 26278-79-5 2-amino-6-hydroxybenzothiazole 

Relevant articles and documents

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Neurodegenerative Therapies

The present invention provides a compound of formula (I) wherein: Y represents a C or N atom which may be substituted or form a cyclic group with R′″ but may not be a quaternary C atom; R′ is —OR1, —CONH2, —CF3, F, —OH, —NO2, —CN or —OCOR1 in which R1, is C1-3 alkyl and each may be in the beta or gamma position; R″ is C1-3 alkyl or H; and R′″ is H or a group consisting of 1-12 non-hydrogen atoms and may be linear, branched and/or incorporate one or more cyclic groups, cyclic groups may be aromatic and/or heterocyclic and 2 or more cyclic groups may be linked or fused and each may be substituted; or a salt, hydrate or solvate of a compound of formula (I) for use in the treatment or prevention of a neurodegenerative disorder by inhibiting formation of neurofibrillary (tau) tangles and/or by inhibiting Dyrk 1A. The invention further relates to non-therapeutic uses of these compounds.