92-36-4

Basic information

• Product Name: 4-(6-Methyl-2-benzothiazolyl)benzeneamine
• Synonyms: 2-(P-AMINOPHENYL)-6-METHYLBENZOTHIAZOLE;2-(4-aminophenyl)-6-methylbenzothiazole;4-(6-methyl-2-benzothiazolyl)benzeneamine;4-(6-METHYL-BENZOTHIAZOL-2-YL)-PHENYLAMINE;4-(6-METHYL-1,3-BENZOTHIAZOL-2-YL)ANILINE;AKOS BBS-00003544;AKOS MSC-0727;AKOS BBB/024
• CAS NO: 92-36-4
• Molecular Formula: C₁₄H₁₂N₂S
• Molecular Weight: 240.32
• EINECS: 202-150-4
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 92-36-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 191-196°C
• Boiling Point: 434°C
• Flash Point: 217.3 °C
• Appearance: /
• Density: 1.1769 (rough estimate)
• Vapor Pressure: 8.62E-08mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.79±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 20℃
• CAS DataBase Reference: 4-(6-Methyl-2-benzothiazolyl)benzeneamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(6-Methyl-2-benzothiazolyl)benzeneamine(92-36-4)
• EPA Substance Registry System: 4-(6-Methyl-2-benzothiazolyl)benzeneamine(92-36-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 92-36-4(Hazardous Substances Data)

Usage

General Description

Light tan or light orange powder. Solutions have a violet-blue fluorescence.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-(6-Methyl-2-benzothiazolyl)benzeneamine is incompatible with strong oxidizing agents, acid chlorides and acid anhydrides.

Fire Hazard

Flash point data for 4-(6-Methyl-2-benzothiazolyl)benzeneamine are not available; however, 4-(6-Methyl-2-benzothiazolyl)benzeneamine is probably combustible.

InChI:InChI=1/C14H12N2S/c1-9-2-7-12-13(8-9)17-14(16-12)10-3-5-11(15)6-4-10/h2-8H,15H2,1H3

Upstream product

• 106-49-0 p-toluidine 
• 79560-96-6 N-(4-amino-benzyl)-p-toluidine 
• 31183-91-2 2-[(2-amino-5-methylphenyl)dithio]-4-methylphenylamine 
• 150-13-0 4-amino-benzoic acid 
• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 3622-19-3 2-bromo-6-methylbenzothiazole 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 488722-57-2 6-methyl-2-(4'-nitrophenyl)-1,3-benzothiazole 
• 23451-96-9 2-amino-5-methylthiophenol 
• 1145-66-0 1-(4-methylphenyl)-3-phenylthiourea 
• 62-53-3 aniline 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 102-08-9 N,N-diphenylthiourea 

Downstream Products

• 2390-54-7 thioflavine T 
• 67229-93-0 4-(6-methyl-2-benzothiazolyl)phenyl isocyanate 
• 32752-83-3 [4-(6-methyl-benzothiazol-2-yl)-anilino]-methanesulfonic acid ; sodium-salt 
• 95856-69-2 formic acid-[4-(6-methyl-benzothiazol-2-yl)-anilide] 
• 10205-63-7 N,N-diethyl-4-(6-methylbenzo[d]thiazol-2-yl)aniline 
• 82654-96-4 N-benzylidene-4-(6-methyl-benzothiazol-2-yl)-aniline 
• 95856-79-4 N-[4-(6-methyl-1,3-benzothiazol-2-yl)phenyl]benzamide 
• 65175-38-4 N-(4-dimethylamino-benzylidene)-4-(6-methyl-benzothiazol-2-yl)-aniline 
• 339223-67-5 4-nitro-benzenesulfonic acid-[4-(6-methyl-benzothiazol-2-yl)-anilide] 
• 10205-62-6 N,N-dimethyl-4-(6-methylbenzo[d]thiazole-2-yl)aniline 
• 47070-20-2 [2-(4-(dimethylamino)phenyl)-3,6-dimethylbenzo[d]thiazol-3-ium] iodide 
• 17205-68-4 bis-[4-(6-methyl-benzothiazol-2-yl)-phenyl]-diazene 
• 106-49-0 p-toluidine 
• 150-13-0 4-amino-benzoic acid 

Relevant articles and documents

Discovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist

Receptor-related orphan receptor γ (RORγ) has emerged as an attractive therapeutic target for the treatment of cancer and inflammatory diseases. Herein, we report our effort on the discovery, optimization, and evaluation of benzothiazole and benzimidazole derivatives as novel inverse agonists of RORγ. The representative compound27h(designated as XY123) potently inhibited the RORγ transcription activity with a half-maximal inhibitory concentration (IC50) value of 64 nM and showed excellent selectivity against other nuclear receptors.27halso potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-positive prostate cancer cell lines. In addition,27hdemonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life (t1/2= 4.98 h). Significantly, oral administration of compound27hachieved complete and long-lasting tumor regression in the 22Rv1 xenograft tumor model in mice. Compound27hmay serve as a new valuable lead compound for further development of drugs for the treatment of prostate cancer.

Discovery of Small Molecules that Induce the Degradation of Huntingtin

Huntington's disease (HD) is an autosomal dominant neurodegenerative disorder caused by the aggregation of mutant huntingtin (mHtt), and removal of toxic mHtt is expected to be an effective therapeutic approach. We designed two small hybrid molecules (1 and 2) by linking a ligand for ubiquitin ligase (cellular inhibitor of apoptosis protein 1; cIAP1) with probes for mHtt aggregates, anticipating that these compounds would recruit cIAP1 to mHtt and induce selective degradation by the ubiquitin-proteasome system. The synthesized compounds reduced mHtt levels in HD patient fibroblasts and appear to be promising candidates for the development of a treatment for HD.

Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions

Abstract A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental analysis. The resin could be easily recovered and reused for subsequent reactions.