24622-34-2

Basic information

• Product Name: 2-Benzothiazolamine,N-2-propenyl-(9CI)
• Synonyms: 2-Benzothiazolamine,N-2-propenyl-(9CI)
• CAS NO: 24622-34-2
• Molecular Formula: C10H10N2S
• Molecular Weight: 190.2648
• Product Categories: BENZOTHIAZOLE
• Mol File: 24622-34-2.mol

Chemical Properties

• Boiling Point: 299.5°Cat760mmHg
• Flash Point: 135°C
• Appearance: /
• Density: 1.236g/cm³
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 2-Benzothiazolamine,N-2-propenyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzothiazolamine,N-2-propenyl-(9CI)(24622-34-2)
• EPA Substance Registry System: 2-Benzothiazolamine,N-2-propenyl-(9CI)(24622-34-2)

Safety Data

• Hazardous Substances Data: 24622-34-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzothiazolamine, N-2-propenyl-(9CI) is utilized as an intermediate in the synthesis of pharmaceutical compounds due to its unique structure and reactivity. Its potential biological activities also make it a candidate for the development of new drugs in medicinal chemistry.
Used in Agriculture:
In the agricultural sector, 2-Benzothiazolamine, N-2-propenyl-(9CI) is employed as an intermediate in the production of agrochemicals, contributing to the development of effective and innovative solutions for crop protection and enhancement.
Used in Materials Science:
2-Benzothiazolamine, N-2-propenyl-(9CI) is used as a building block in the synthesis of various materials, such as polymers and composites, due to its versatile chemical properties. This allows for the creation of new materials with improved properties for various applications in the materials science field.

InChI:InChI=1/C10H10N2S/c1-2-7-11-10-12-8-5-3-4-6-9(8)13-10/h2-6H,1,7H2,(H,11,12)

Upstream product

• 30719-59-6 N-allyl-N'-(2-amino-phenyl)-thiourea 
• 136-95-8 2-amino-benzthiazole 
• 201230-82-2 carbon monoxide 
• 106-95-6 allyl bromide 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 107-11-9 1-amino-2-propene 

Relevant articles and documents

Convenient and reliable routes towards 2-aminothiazoles: Palladium-catalyzed versus copper-catalyzed aminations of halothiazoles

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key molecules in pharmaceutical research. Copyright

Laccase-catalysed homocoupling of primary aromatic amines towards the biosynthesis of dyes

Coloured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p-electron donor pri-mary aromatic amines using two different laccases, CotA-laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange-red to purple products, presenting high molar extinction coeffi-cients, presumably result from oxidative homocou-pling reactions, through the formation of N-C bonds at positions 2 and 5, of the laccase oxidised inter-mediate as showed in the proposed oxidative path-way. The product of 1,4-phenylenediamine is shown to be the trimer known as Bandrowski's base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p-electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data con-tribute for (i) understanding key features of laccase reactivity with p-substituted aromatic amines and (ii) establishing enzymatic processes that lead to the syn-thesis of coloured bio-products under mild condi-tions with potential impact in the cosmetic and dye industries.

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).

One-pot amide synthesis from allyl or benzyl halides and amines by Pd-catalysed carbonylation

Amides can be prepared from allyl or benzyl halides and primary or secondary amines, using Pd(0) catalyst under CO pressure, in a one-pot synthesis. The reaction proceeds through the acyl palladium halide formation which undergoes an acylic nucleophilic substitution from the amine.