6-Methoxy-2-tetralone Chemical Properties

Melting point:

28-35 °C

Boiling point:

114-116 °C (0.2 mmHg)

Density 

1.0431 (rough estimate)

refractive index 

n20/D 1.5645(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Crystalline Low Melting Solid

color 

Light yellow-beige to orange

Sensitive 

Air Sensitive

BRN 

513418

InChI

InChI=1S/C11H12O2/c1-13-11-5-3-8-6-10(12)4-2-9(8)7-11/h3,5,7H,2,4,6H2,1H3

InChIKey

RMRKDYNVZWKAFP-UHFFFAOYSA-N

SMILES

C1C2=C(C=C(OC)C=C2)CCC1=O

CAS DataBase Reference

2472-22-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29145090

MSDS

• Language:English Provider:6-Methoxy-2-tetralone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-Methoxy-2-tetralone Usage And Synthesis

Description

6-methoxy-2-tetralone has been selected as the starting material for the synthesis of many steroidal compounds, including 2-aminotetalin derivatives, which exhibit antifungal activities, tetrahydro benzocycloheptane and many terpenoid compounds. 6-methoxy-2-tetralone is more expensive, difficult to synthesize, and unstable in comparison to 6-methoxy-1-tetralone[1].

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.9.267
The Journal of Organic Chemistry, 26, p. 3237, 1961 DOI: 10.1021/jo01067a049

Synthesis

To a suspension of MCPBA (1.5g, 8.7mmol) in dry dichloromethane (16mL), cooled in ice, was added dihydro naphthalene (616mg, 3.8mmol) dissolved in dichloromethane (2mL). The reaction mixture was stirred overnight, filtered, diluted with dichloromethane, washed with a solution of sodium bicarbonate (5%), brine, dried, and evaporated to obtain an oil (591mg), which without purification was dissolved in ethanol (3mL) and treated with sulfuric acid (3mL, 10%) and heated under reflux for 3 hours. The reaction mixture was cooled, diluted with water, and extracted three times using chloroform. The organic extracts were washed with brine, dried, and evaporated to obtain an oil which, on purification (eluent hexane: ether 7:3), afforded 6-Methoxy-2-tetralone.

References

[1] Banerjee, A. K. et al. “A concise approach for the synthesis of 6-methoxy-2-tetralone.” 2018. 0.

6-Methoxy-2-tetralone (2472-22-2)Related Product Information

• 1,2,3,4-Tetrahydronaphthalene
• Decahydronaphthalene
• 1-Tetralone
• Nabumetone
• 6,7-Dimethoxy-2-tetralone
• 6,8-Dimethoxyl-2-tetralone
• 6,7-Dimethoxy-1-tetralone
• Methoxy-2-tetralone,5-,5-METHOXY-2-TETRALONE
• 6-Methoxy-1-Tetralone99%
• 8-METHOXY-2-TETRALONE
• 7-Methoxy-2-Tetralone(7-OHO),7-METHOXY-2-TETRALONE
• 7-METHOXY-1-TETRALONE,99.5+%,7-METHOXY-1-TETRALONE,7-Methoxy-1-tetralone/CH79635,7-Methoxy-1-tetralone,99%
• 6-methoxy-1-tetralone
• 8-Methoxy-α-Tetralone,8-METHOXY-A-TETRALONE,8-METHOXY-1-TETRALONE
• 5-METHOXY-1-TETRALONE,5-Methoxy-1-tetralone,97%,5-METHOXY-1-TETRALONE 97%,5-METHOXY-1-TETRALONE TECH 94+%
• 5-Chloro-8-methoxyl-2-tetralone
• 5,8-Dimethoxy-2-tetralone
• 6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALENE