6-Methoxy-2-tetralone
Synonym(s):6-Methoxy-2-tetralone
- CAS NO.:2472-22-2
- Empirical Formula: C11H12O2
- Molecular Weight: 176.21
- MDL number: MFCD00001729
- EINECS: 219-592-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-06-04 15:29:52
What is 6-Methoxy-2-tetralone ?
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
The Uses of 6-Methoxy-2-tetralone
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.
Properties of 6-Methoxy-2-tetralone
Melting point: | 28-35 °C |
Boiling point: | 114-116 °C (0.2 mmHg) |
Density | 1.0431 (rough estimate) |
refractive index | n |
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 |
CAS DataBase Reference | 2472-22-2(CAS DataBase Reference) |
Safety information for 6-Methoxy-2-tetralone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P233:Keep container tightly closed. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304:IF INHALED: P312:Call a POISON CENTER or doctor/physician if you feel unwell. P321:Specific treatment (see … on this label). P340:Remove victim to fresh air and keep at rest in a position comfortable for breathing. P362:Take off contaminated clothing and wash before reuse. P302+P352:IF ON SKIN: wash with plenty of soap and water. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. P403:Store in a well-ventilated place. P405:Store locked up. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P501:Dispose of contents/container to..… |
Computed Descriptors for 6-Methoxy-2-tetralone
InChIKey | RMRKDYNVZWKAFP-UHFFFAOYSA-N |
SMILES | C1C2=C(C=C(OC)C=C2)CCC1=O |
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