24224-30-4

Basic information

• Product Name: 3-methyl-9H-carbazol-2-ol
• Synonyms: 3-methyl-9H-carbazol-2-ol;2-Hydroxy-3-methylcarbazole
• CAS NO: 24224-30-4
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23254
• Mol File: 24224-30-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 245-246 °C
• Boiling Point: 430.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.308±0.06 g/cm3(Predicted)
• PKA: 10.39±0.30(Predicted)
• CAS DataBase Reference: 3-methyl-9H-carbazol-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-9H-carbazol-2-ol(24224-30-4)
• EPA Substance Registry System: 3-methyl-9H-carbazol-2-ol(24224-30-4)

Safety Data

• Hazardous Substances Data: 24224-30-4(Hazardous Substances Data)

Usage

General Description

3-Methyl-9H-carbazol-2-ol, also known as 3-methylcarbazole-2-ol, is a chemical compound with the molecular formula C13H11NO. It is a derivative of carbazole, a heterocyclic compound with a nine-membered ring structure containing nitrogen. 3-Methyl-9H-carbazol-2-ol is a pale yellow to brown solid that is used in various industrial applications, including as a dye intermediate, a polymerization catalyst, and a chemical intermediate for pharmaceuticals. It is also a potential candidate for use in organic electronics. The compound has been studied for its antioxidant, antibacterial, and antifungal properties, and it has shown potential therapeutic effects in the treatment of neurodegenerative diseases.

Upstream product

• 4630-20-0 3-Methyl-9H-carbazole 
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• 1197392-20-3 3-(tert-butyldiphenylsilyloxy)-4-methylaniline 
• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 
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• 108-86-1 bromobenzene 

Downstream Products

• 21104-28-9 mahanimbine 
• 23095-44-5 girinimbine 
• 27300-29-4 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde 
• 25488-37-3 mahanimbidine 
• 166990-10-9 (-)-murrayamine-O 
• 166990-10-9 (+)-murrayamine-O 
• 166990-10-9 (-)-murrayamine P 
• 166990-10-9 (+)-murrayamine P 
• 17750-35-5 2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde 

Relevant articles and documents

Asymmetric oxidative coupling of hydroxycarbazoles: Facile synthesis of (+)-bi-2-hydroxy-3-methylcarbazole

Asymmetric oxidative coupling reactions of hydroxycarbazoles have been established using a chiral dinuclear vanadium complex. To demonstrate the utility of vanadium-catalyzed reactions, we have used them to synthesize (+)-bi-2-hydroxy-3-carbazole in three steps from cyclohexanone and commercially available aniline derivatives.

Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke.

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Br?nsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee.