32940-15-1

Basic information

• Product Name: 5-Methoxy-2-tetralone
• Synonyms: 2(1H)-NAPHTHALENONE, 3,4-DIHYDRO-5-METHOXY-;5-METHOXY-3,4-DIHYDRO-1H-NAPHTHALEN-2-ONE;5-METHOXY-2-TETRALONE;5M2T;5-METHOXY-3,4-DIHYDRONAPHTHALEN-2(1H)-ONE;5-Methoxyl-2-Tetralone;Methoxy-2-tetralone,5-;5-Methoxy-3,4-dihydronaphthalen-2(1H)-one 97%
• CAS NO: 32940-15-1
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• Product Categories: Naphthalene derivatives;Fused Ring Systems;C11 to C12;Carbonyl Compounds;Ketones;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 32940-15-1.mol

Chemical Properties

• Melting Point: 32-36 °C(lit.)
• Boiling Point: 165°C/10mmHg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.124 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• BRN: 1451623
• CAS DataBase Reference: 5-Methoxy-2-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-tetralone(32940-15-1)
• EPA Substance Registry System: 5-Methoxy-2-tetralone(32940-15-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 32940-15-1(Hazardous Substances Data)

Usage

Chemical Properties

Orange Solid

Uses

Intermediate in the production of Rotigotine

InChI:InChI=1/C11H12O2/c1-13-11-4-2-3-8-7-9(12)5-6-10(8)11/h2-4H,5-7H2,1H3

Upstream product

• 74-85-1 ethene 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 1190847-91-6 C₁₅H₂₄O₄ 
• 1160858-14-9 C₁₃H₁₆O₅ 
• 33892-75-0 5-Methoxy-1-tetralone 
• 60573-59-3 8-Methoxy-1,2-dihydronaphthalene 
• 28033-63-8 2-(2-methoxyphenyl)acetyl chloride 
• 135-02-4 ortho-anisaldehyde 
• 90-02-8 salicylaldehyde 
• 121985-99-7 2-hydroxy-2-(2-methoxyphenyl)acetonitrile 
• 124067-29-4 3-(2-anisyl)-α-diazo-2-propanone 
• 1011-54-7 2-methoxycinnamic acid 
• 93-25-4 2-methoxyphenylacetic acid 
• 22955-75-5 3-(2-methoxyphenyl)propionyl chloride 

Downstream Products

• 93601-86-6 (S)-(-)-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine hydrochloride 
• 1433830-21-7 C₁₈H₂₀N₂O₃S 
• 1321942-91-9 N-(5-methoxy-3,4-dihydronaphthalen-2-yl)propionamide 
• 102120-95-6 5-methoxy-N-2'-(thien-2-yl)ethyltetralin-2-amine 
• 1381993-84-5 (E)-1-(2,3,4-trimethoxybenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-60-7 (E)-1-(3,4-dichlorobenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-66-3 (E)-1-(4-dimethylaminobenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-48-1 (E)-1-(4-bromobenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-75-4 (E)-1-(3,4-dimethoxybenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-72-1 (E)-1-(4-hydroxy-3-methoxybenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-57-2 (E)-1-(2,4-dichlorobenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-30-1 (E)-1-(4-methoxybenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-39-0 (E)-1-(4-hydroxybenzylidene)-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 
• 1381993-27-6 (E)-1-benzylidene-5-methoxy-3,4-dihydronaphthalen-2(1H)-one 

Relevant articles and documents

An unexpected double-bond isomerization catalyzed by Crabtree's iridium(I) catalyst

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Synthesis and Dopaminergic Activity of 2-Substituted Octahydrobenzoquinolines

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Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant

Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.

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A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

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