56048-54-5

Basic information

• Product Name: 2-(2-BENZOTHIAZOLYL)-5-METHYLPHENOL
• Synonyms: 2-(1,3-Benzothiazol-2-yl)-5-methylphenol;2-(2-HYDROXY-4-METHYLPHENYL)BENZOTHIAZOLE;2-(2-BENZOTHIAZOLYL)-5-METHYLPHENOL;2-(2-BENXOTHIAZOLYL)-5-METHYLPHENOL;TIMTEC-BB SBB007905;2-(2-HYDROXY-4-METHYLPHENYL)BENZOTHIAZOLE ---WHITE CRYSTALLINE---
• CAS NO: 56048-54-5
• Molecular Formula: C₁₄H₁₁NOS
• Molecular Weight: 241.31
• Mol File: 56048-54-5.mol

Chemical Properties

• Boiling Point: 410.6 °C at 760 mmHg
• Flash Point: 202.1 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Refractive Index: 1.684
• PKA: 8.18±0.35(Predicted)
• CAS DataBase Reference: 2-(2-BENZOTHIAZOLYL)-5-METHYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-BENZOTHIAZOLYL)-5-METHYLPHENOL(56048-54-5)
• EPA Substance Registry System: 2-(2-BENZOTHIAZOLYL)-5-METHYLPHENOL(56048-54-5)

Safety Data

• Hazardous Substances Data: 56048-54-5(Hazardous Substances Data)

Usage

Uses

Used in Rubber and Plastic Industries:
2-(2-Benzothiazolyl)-5-methylphenol is used as an antioxidant for the protection of rubber and plastic materials against heat and oxygen-induced degradation. It helps in maintaining the durability and performance of these materials by inhibiting oxidation reactions.
Used in Dyes and Pigments Production:
2-(2-Benzothiazolyl)-5-methylphenol is used as an intermediate in the production of dyes and pigments. Its unique chemical structure contributes to the development of various colorants used in different industries.
Used in Pharmaceutical Synthesis:
2-(2-Benzothiazolyl)-5-methylphenol is also utilized in the synthesis of pharmaceuticals. Its chemical properties make it a valuable component in the development of various drugs.
Safety Precautions:
It is important to handle and use 2-(2-benzothiazolyl)-5-methylphenol with proper safety measures, as it can be harmful if ingested or inhaled and may cause skin and eye irritation. Adequate protective equipment and handling procedures should be followed to minimize potential risks.

InChI:InChI=1/C14H11NOS/c1-9-6-7-10(12(16)8-9)14-15-11-4-2-3-5-13(11)17-14/h2-8,15H,1H3/b14-10-

Upstream product

• 50-85-1 2-hydroxy-p-toluic acid 
• 137-07-5 2-amino-benzenethiol 
• 16112-21-3 2-(4-methylphenyl)-1,3-benzothiazole 
• 698-27-1 4-methylsalicylaldehyde 
• 1141-88-4 2-Aminophenyl disulfide 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 263153-50-0 2-[2-[(methoxymethyl)oxy]-4-methylphenyl]benzothiazole 
• 263153-51-1 2-[2-[(methoxymethyl)oxy]-4-(bromomethyl)phenyl]benzothiazole 
• 263153-90-8 2-(tritylamino)-α-[[3-[(methoxymethyl)oxy]-4-(2-benzothiazolyl)benzyloxy]imino]-4-thiazoleacetic acid 
• 263154-23-0 [(Z)-4-Benzothiazol-2-yl-3-methoxymethoxy-benzyloxyimino]-[2-(trityl-amino)-thiazol-4-yl]-acetic acid allyl ester 
• 263154-24-1 (2R,3S)-3-{2-[(Z)-4-Benzothiazol-2-yl-3-methoxymethoxy-benzyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid 

Relevant articles and documents

A ratiometric fluorescent probe for rapid, sensitive and selective detection of sulfur dioxide with large Stokes shifts by single wavelength excitation

4-(Benzothiazol-2-yl)-3-hydroxybenzaldehyde, probe 1, has been developed as a ratiometric fluorescent probe for the sensitive and selective detection of sulfur dioxide with a fast response time (within seconds). This probe itself exhibited a yellow emissi

HBT-based methyl derivative fluorescent probe and preparation and application thereof

The invention provides a fluorescent probe 5-HBT as well as preparation and application of the fluorescent probe 5-HBT to fluorescence detection through research on introduction of methyl groups at different positions on a benzene ring of an HBT molecule, so residual sodium hypochlorite in a water body can be rapidly and visually detected on site. Studies prove that the position of a methyl group on a benzene ring can generate huge influence on some fluorescent molecules, mainly including fluorescence intensity and fluorescence stability, and most obviously, 5-HBT fluorescence is greatly weakened; and the obtained 5-HBT probe can emit fluorescence in a solid state, has great advantages when used for manufacturing a paper fluorescence sensor, is obvious in fluorescence effect, and can rapidly and visually detect a sodium hypochlorite solution on site.

Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis

This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.

Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions

The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)2 as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.

Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine

A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.

Metal-free synthesis of benzothiazoles from disulfides of 2-aminobenzenethiol and carboxylic acid via PCl3-promoted tandem reaction

A metal-free process for the synthesis of benzothiazoles via PCl3-promoted cleavage/acylation/ cyclization of disulfides and carboxylic acids has been developed. In addition to acting as the acylating reagent which converted carboxylic acids into acyl chlorides, PCl3 also converted disulfides to thiols, which promoted disulfides of 2-aminobenzenethiol reacted with carboxylic acid to produce benzothiazoles. The developed method is applicable to a wide range of carboxylic acids containing different functional groups.

FeCl3/ultrasound mediated reaction of 2-aminothiophenol with aldehydes in water: Synthesis of 2-substituted benzothiazoles of pharmacological interest

We report a FeCl3?6H2O mediated green and rapid access to benzothiazole derivatives having a substituent at C-2 via the condensation of 2-aminothiophenol with various aldehydes under ultrasound irradiation and air. The reaction progressed well in water affording the expected products in good yields. Two of these compounds known to be potent anticancer agents showed good interactions with PDE4B in silico and inhibited this enzyme when tested in vitro.

Regioselective ortho-hydroxylation of 2-arylbenzothiazole via substrate directed C-H activation

An efficient protocol has been developed for the direct ortho-hydroxylation of 2-arylbenzothiazole using Pd(OAc)2 as the catalyst and either of DIB/AcOH or Oxone/TFA combinations under air atmosphere. Under both these conditions, the methodology tolerates a diverse array of substituents giving good to excellent yields of corresponding ortho-hydroxylated products. Regioselective hydroxylation is observed at the less sterically hindered site of the phenyl ring possessing substituents at its meta position.

Correlation between molecular structure and optical properties for the bis(2-(2-hydroxyphenyl)benzothiazolate) complexes

A series of methyl-substituted bis(2-(hydroxyphenyl)benzothiazolate)zinc derivatives [Zn(n-MeBTZ)2, n = 3 (1a), 4 (1b), 5 (1c)] were synthesized to investigate the correlation between molecular structures and optical properties. The results indicate that the blue-emitting (λmax = 470 nm) complex 1b is monomer with a higher PL quantum efficiency than complexes 1, 1a, 1c. Two green-emitting (λmax = 507 nm and 499 nm) complexes 1a and 1c have special bi-molecular structures. The molecular structure for Zn(BTZ)2 (complex 1) is dimer. Bilayer organic light-emitting devices were fabricated by using these complexes as emitting layer. The maximum emission wavelengths of the devices are in the range of 501-553 nm. The devices show turn-on voltages at 9.2, 12.7, 2.3 and 10.7 V for complex 1, 1a, 1b, and 1c, respectively. In particular, the device with complex 1b shows a higher brightness than the other complexes under the same conditions.

Solid-state Fluorescent Photophysics of Some 2-Substituted Benzothiazoles

The solid-state fluorescence properties of a series of benzothiazoles with phenyl, napthalene, and coumarin moieties substituted at the 2-position have been investigated.The necessity for a 2'-OH substituent for fluorescence has been confirmed and the effects of further substitution in the 2-phenyl ring are reported.