16954-69-1

Basic information

• Product Name: N-methylbenzothiazol-2-amine
• Synonyms: N-methylbenzothiazol-2-amine;2-MethylAminoBenzethiazole;2-Benzothiazolamine,N-methyl-(9CI);N-METHYL-1,3-BENZOTHIAZOL-2-AMINE HYDROBROMIDE;2-(Methylamino)benzothiazole;N-Methylbenzo[d]thiazol-2-aMine
• CAS NO: 16954-69-1
• Molecular Formula: C₈H₈N₂S
• Molecular Weight: 164.22752
• EINECS: 241-025-9
• Product Categories: BENZOTHIAZOLE;Thiazoles
• Mol File: 16954-69-1.mol
• Article Data: 27

Chemical Properties

• Melting Point: 140-142°
• Boiling Point: 270.1 °C at 760 mmHg
• Flash Point: 117.2 °C
• Appearance: /
• Density: 1.306 g/cm³
• Vapor Pressure: 0.00697mmHg at 25°C
• Refractive Index: 1.73
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.13±0.10(Predicted)
• CAS DataBase Reference: N-methylbenzothiazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylbenzothiazol-2-amine(16954-69-1)
• EPA Substance Registry System: N-methylbenzothiazol-2-amine(16954-69-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16954-69-1(Hazardous Substances Data)

Usage

General Description

N-methylbenzothiazol-2-amine is a chemical compound with the molecular formula C8H9NHS. It is an organic compound with a benzothiazole backbone and a methyl group attached to the nitrogen atom. This chemical is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and dyes. It is also used as a rubber accelerator and in the production of antioxidants and antidegradants for rubber products. N-methylbenzothiazol-2-amine is known for its potential toxic and irritant effects, so proper handling and safety precautions should be taken when working with this compound.

InChI:InChI=1/C8H8N2S/c1-9-8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H,9,10)

Upstream product

• 34551-29-6 4-methyl-5-phenylimino-Δ²-1,2,3,4-thiatriazoline 
• 52599-27-6 N-(2-bromo-phenyl)-N'-methyl-thiourea 
• 615-43-0 2-iodophenylamine 
• 556-61-6 methyl thioisocyanate 
• 136-95-8 2-amino-benzthiazole 
• 50-00-0 formaldehyd 
• 116928-25-7 benzo[d]thiazol-2-yltriphenylphosphonium trifluoromethanesulfonate 
• 74-89-5 methylamine 
• 95-16-9 1,3-Benzothiazole 
• 67-56-1 methanol 
• 103-72-0 phenyl isothiocyanate 
• 6919-36-4 1-hydroxy-1-methyl-3-phenylthiourea 
• 615-36-1 2-bromoaniline 
• 95-51-2 o-chloroaniline 

Downstream Products

• 18691-97-9 methabenzthiazuron 
• 90349-90-9 N--N-methyl-thiocarbamid 
• 92969-18-1 1-benzothiazol-2-yl-2-benzyl-1-methyl-isothiourea 
• 53065-94-4 1-benzothiazol-2-yl-1-methyl-urea 
• 53159-45-8 1-Benzthiazol-1yl-1-methyl-3-hydroxymethylharnstoff 
• 53065-93-3 N-(benzothiazolyl-2)-N-methylformamid 
• 118215-11-5 N-Benzothiazol-2-yl-N-methyl-thiobenzamide 
• 97684-79-2 2-Benzyl-3,4-bis(diethylamino)-1H-pyrido<2,1-b>benzothiazol-1-on 
• 97684-80-5 3,4-Bis(diethylamino)-2-phenyl-1H-pyrido<2,1-b>benzothiazol-1-on 
• 97684-77-0 3,4-Dibenzoyl-2-methyl-1H-pyrido<2,1-b>benzothiazol-1-on 
• 97684-87-2 2-Benzyl-3-diethylamino-4-methyl-1H-pyrido<2,1-b>benzothiazol-1-on 
• 97684-76-9 3,4-Dibenzoyl-1H-pyrido<2,1-b>benzothiazol-1-on 
• 97684-84-9 2-Benzyl-1-oxo-1H-pyrido<2,1-b>benzothiazol-4-carbonsaeure-methylester 
• 97684-88-3 3-Diethylamino-4-methyl-2-phenyl-1H-pyrido<2,1-b>benzothiazol-1-on 

Relevant articles and documents

One-pot synthesis of 2-aminobenzothiazoles using a new reagent of [Bmim]Br3 in [Bmim]BF4

The one-pot direct synthesis of 2-aminobenzothiazoles from phenyl isothiocyanate and amines using a new reagent of 1-butyl-3-methylimidazolium tribromide ([Bmim]Br3) in ionic liquid 1-butyl-3-methyl-imidazolium tetraflouoroborate ([Bmim]BF4) is described.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.