2472-22-2

Basic information

• Product Name: 6-Methoxy-2-tetralone
• Synonyms: 3,4-DIHYDRO-6-METHOXY-2(1H)-NAPHTHALENONE;6-methoxy-1,2,3,4-tetrahydronaphthalen-2-one;6-Methoxy-3,4-dihydro-2(1H)-naphthalenone, 95%;6-Methoxy-2-tetralone,tech.90%;6-methoxy-3,4-dihydro-1H-naphthalene-2-one;3,4-Dihydro-6-methoxynaphthalen-2(1H)-one;6-methoxy-2-Tetrlone;6-methoxy-3,4-dihydronaphthalen-2-one
• CAS NO: 2472-22-2
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• EINECS: 219-592-9
• Product Categories: pharmacetical;Naphthalenes;Fused Ring Systems
• Mol File: 2472-22-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 28-35 °C
• Boiling Point: 114-116 °C (0.2 mmHg)
• Flash Point: >230 °F
• Appearance: Light yellow-beige to orange/Crystalline Low Melting Solid
• Density: 1.0431 (rough estimate)
• Vapor Pressure: 6.9E-05mmHg at 25°C
• Refractive Index: n20/D 1.5645(lit.)
• Storage Temp.: 0-6°C
• Sensitive: Air Sensitive
• BRN: 513418
• CAS DataBase Reference: 6-Methoxy-2-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-2-tetralone(2472-22-2)
• EPA Substance Registry System: 6-Methoxy-2-tetralone(2472-22-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2472-22-2(Hazardous Substances Data)

Usage

Chemical Properties

light yellow-beige to orange

Uses

6-Methoxy-3,4-dihydro-2(1H)-naphthalenone was used in the synthesis of 1, 2, 3, 4-tetrahydro-2-naphthylamine derivatives.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 9, p. 267, 1961 DOI: 10.1248/cpb.9.267The Journal of Organic Chemistry, 26, p. 3237, 1961 DOI: 10.1021/jo01067a049

InChI:InChI=1/C5H8N4.ClH/c1-2-9-4-7-8-5(9)3-6-1;/h4,6H,1-3H2;1H

Upstream product

• 52178-91-3 7-methoxy-1,2-dihydronaphthalene 
• 65472-33-5 3,7-dimethoxy-1,2-dihydro-naphthalene 
• 16821-34-4 cis-6-methoxy-1,2,3,4-tetrahydronaphthalene-1,2-diol 
• 73706-61-3 1-tosyloxy-4-(3-methoxyphenyl)-2-butanone 
• 2311-91-3 monoperoxyphthalic acid 
• 60-29-7 diethyl ether 
• 93-59-4 Perbenzoic acid 
• 75-09-2 dichloromethane 
• 7647-01-0 hydrogenchloride 
• 5486-55-5 2,6-dimethoxylnaphthalene 
• 66227-90-5 1-(trimethylsilyl)-3,4-dihydro-6-methoxynaphthalene 
• 115375-59-2 6-methoxy-3,4-dihydronaphthalene-1-yl triflate 
• 1190847-92-7 C₁₅H₂₄O₄ 
• 1160858-15-0 C₁₃H₁₆O₅ 

Downstream Products

• 873965-14-1 6-methoxy-1-(3-methoxy-phenethyl)-3,4-dihydro-1H-naphthalen-2-one 
• 71886-83-4 6-methoxy-1,1-dimethyl-3,4-dihydronaphthalene-2(1H)-one 
• 82763-23-3 N-propyl-6-methoxy-2-aminotetralin 
• 93877-51-1 6-methoxy-2-(p-methoxyphenyl)-3,4-dihydronaphthalene 
• 98130-18-8 3,4-Dihydro-6-methoxy-2-(4-methoxy-m-tolyl)-naphthalin 
• 22117-57-3 3,4-Dihydro-6-methoxy-2-phenylnaphthalene 
• 52727-28-3 6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-one 
• 38820-34-7 2,3,4,4a,9,10-hexahydro-7-methoxy-1,4aβ-dimethyl-2-phenanthrone 
• 90397-76-5 Benzenesulfonyl-acetic acid (1R,2R,4aR,4bS,9S,10aR)-2-methoxy-1,4a-dimethyl-7-oxo-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-9-yl ester 
• 90397-77-6 (4aS,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-decahydro-7-oxa-cyclopenta[k]phenanthrene-3,6-dione 
• 100467-47-8 (3R,3aS,4R,4aS,7S,8S,8aS,9aR)-3-Benzenesulfonyl-7-methoxy-4a,8-dimethyl-2-oxo-4-(3-oxo-propyl)-decahydro-naphtho[2,3-b]furan-3a-carbaldehyde 
• 100467-46-7 (4R,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-3,4-dihydroxy-10-methoxy-9,12a-dimethyl-dodecahydro-7-oxa-cyclopenta[k]phenanthren-6-one 
• 91186-27-5 C₂₅H₃₂O₇S 
• 100467-45-6 (4R,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-4-hydroxy-10-methoxy-9,12a-dimethyl-decahydro-7-oxa-cyclopenta[k]phenanthrene-3,6-dione 

Relevant articles and documents

Synthesis and biological evaluation of 7-methoxy-1-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2H-benzo[e]indazoles as new colchicine site inhibitors

The colchicine site inhibitors (CSIs) displayed both antimitotic and vascular disrupting activities, therefore are promising potential antitumor agents. In this study, a series 1-phenyl-4,5-dihydro-2H-benzo[e]indazoles were found as new CSIs of which the bioactive configuration was locked. Among them, compounds C1 and C2 displayed the best activity, with tubulin polymerization IC50 of 3.4 and 1.5 μM, and growth IC50 of low nanomolar concentrations against human colon cancer cell lines. In addition, compound C1 showed excellent broad-spectrum antitumor activity in the NCI-60 Human Tumor Cell Lines Screen, encouraging further study of this antitumor compound.

Carbonyl 1,2-transposition through triflate-mediated a-amination

To date, it remains challenging to selectively migrate a carbonyl oxygen within a given molecular scaffold, especially to an adjacent carbon. In this work, we describe a simple one- or two-pot protocol that transposes a ketone to the vicinal carbon. This approach first converts the ketone to the corresponding alkenyl triflate, which can then undergo the palladium- and norbornene-catalyzed regioselective a-amination and ipso-hydrogenation enabled by a bifunctional hydrogen and nitrogen donor. The resulting "transposed enamine" intermediate can subsequently be hydrolyzed to produce the 1,2-carbonyl-migrated product. This method allows rapid access to unusual bioactive analogs through late-stage functionalization.

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

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.