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6-Methoxy-1H-indanone

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6-Methoxy-1H-indanone Basic information
Product Name:6-Methoxy-1H-indanone
Synonyms:6-METHOXY-INDAN-1-ONE;6-METHOXY-1H-INDANONE;6-METHOXY-1-INDANONE;6-METHOXY-1-INDANONE, 97+%;6-Methoxy-I-indanone;6-Methoxy-1-indenone;6-METHOXY INDANONE;2,3-Dihydro-6-methoxy-1H-inden-1-one
CAS:13623-25-1
MF:C10H10O2
MW:162.19
EINECS:603-948-9
Product Categories:Indane/Indanone and Derivatives;indanone;Aromatics Compounds;Aromatics;C10;Carbonyl Compounds;Ketones
Mol File:13623-25-1.mol
6-Methoxy-1H-indanone Structure
6-Methoxy-1H-indanone Chemical Properties
Melting point 105-109 °C (lit.)
Boiling point 228.88°C (rough estimate)
density 1.0281 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. Sealed in dry,Room Temperature
form Fine Crystalline Powder
color White to yellow
BRN 1238602
InChIInChI=1S/C10H10O2/c1-12-8-4-2-7-3-5-10(11)9(7)6-8/h2,4,6H,3,5H2,1H3
InChIKeyUJGDLLGKMWVCPT-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=CC(OC)=C2)CC1
CAS DataBase Reference13623-25-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/37/38
Safety Statements 22-24/25-36/37-36-26
WGK Germany 3
HS Code 29145090
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Acute 1
Aquatic Chronic 1
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
6-Methoxy-1H-indanone Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
UsesIndanone derivative as a1-adrenoceptor antagonist.
UsesIndanone derivative as α1-adrenoceptor antagonist.
Uses6-Methoxy-1-indanone was used in the synthesis of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione).
Synthesis Reference(s)Journal of the American Chemical Society, 71, p. 1092, 1949 DOI: 10.1021/ja01171a092
Synthesis
3-(4-Methoxyphenyl)propionic acid

1929-29-9

6-Methoxy-1H-indanone

13623-25-1

General procedure for the synthesis of 6-methoxy-1-indanone from 3-(4-methoxyphenyl)propionic acid: trifluoromethanesulfonic acid (3 eq.) was slowly added to a solution of 3-(4-methoxyphenyl)propionic acid (0.5 mmol) dissolved in anhydrous CH2Cl2 (1.0 mL) in a 12 mL Q-tubepressure tube (provided by QLabtech). The reaction mixture was then warmed to room temperature. A PTFE septum was placed on top of the reaction tube and sealed with the appropriate cap and pressure adapter. The sealed reaction tube was heated in an oil bath at 80°C. The reaction process was monitored by thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC/MS) until the feedstock completely disappeared. After completion of the reaction, the mixture was poured into ice water and extracted three times with CH2Cl2. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. Finally, the target compound 6-methoxy-1-indanone was purified from the crude product by fast column chromatography.

Purification MethodsCrystallise it from MeOH, then sublime it at high vacuum. [Beilstein 8 IV 894.]
References[1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 470 - 475
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[4] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
Tag:6-Methoxy-1H-indanone(13623-25-1) Related Product Information
DONEPEZIL HYDROCHLORIDE Donepezil 6-Methoxy-1H-indanone 4-METHOXY-1-INDANONE 5-METHOXY-1-INDANONE-3-ACETIC ACID Flosulide 5,6-Dimethoxy-1-indanone 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine 4,5-DIMETHOXY-1-INDANONE 5-Methoxy-1-indanone Ethyl 2,3-dihydro-5,6-dimethoxy-1-oxo-1H-indene-2-carboxylate 1-Indanone 2-BROMO-2,3-DIHYDRO-5,6-DIMETHOXY-1H-INDEN-1-ONE 4,5,6-TRIMETHOXY-INDANONE 4-Bromo-6,7-dimethoxyindanone 5-METHOXYNINHYDRIN MONOHYDRATE 1H-Indene-4-carboxylic acid, 2,3-dihydro-6,7-dimethoxy-1-oxo- 5,6-DIMETHOXY-2-((3-PHENOXYPHENYL)METHYLENE)INDAN-1-ONE