| Identification | More | [Name]
6-Methoxy-1H-indanone | [CAS]
13623-25-1 | [Synonyms]
6-METHOXY-1H-INDANONE
6-METHOXY-1-INDANONE
6-METHOXY-INDAN-1-ONE
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
6-Methoxyindane-1-one
NSC 338231
6-Methoxy-2,3-dihydro-1H-indene-1-one | [EINECS(EC#)]
603-948-9 | [Molecular Formula]
C10H10O2 | [MDL Number]
MFCD00021232 | [Molecular Weight]
162.19 | [MOL File]
13623-25-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [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 | [Usage]
Indanone derivative as a1-adrenoceptor antagonist. | [BRN ]
1238602 | [InChI]
InChI=1S/C10H10O2/c1-12-8-4-2-7-3-5-10(11)9(7)6-8/h2,4,6H,3,5H2,1H3 | [InChIKey]
UJGDLLGKMWVCPT-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=CC(OC)=C2)CC1 | [CAS DataBase Reference]
13623-25-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29145090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
6-Methoxy-1-indanone was used in the synthesis of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione). | [Uses]
Indanone derivative as a1-adrenoceptor antagonist. | [Uses]
Indanone derivative as α1-adrenoceptor antagonist. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 71, p. 1092, 1949 DOI: 10.1021/ja01171a092 | [Synthesis]
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-tube?pressure 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 Methods]
Crystallise 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 |
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