| Identification | More | [Name]
2'-Hydroxy-5'-methoxyacetophenone | [CAS]
705-15-7 | [Synonyms]
1-(2-HYDROXY-5-METHOXYPHENYL)ETHAN-1-ONE
1-(2-HYDROXY-5-METHOXYPHENYL)ETHANONE
2'-HYDROXY-5'-METHOXYACETOPHENONE
2-HYDROXY-5'-METHOXYACETOPHENONE
2-HYDROXY-5-METHOXYACETOPHENONE
2'-HYDROXY-5'-METHOXYACETYLPHENONE
ASISCHEM D38760
5-Methoxy-2-hydroxyacetophenone
Acetophenone, 2'-hydroxy-5'-methoxy-
2'-HYDROXY-5'-METHOXYACETOPHENONE,99% | [EINECS(EC#)]
211-882-3 | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00008731 | [Molecular Weight]
166.17 | [MOL File]
705-15-7.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline powder | [Melting point ]
52 °C(lit.) | [Boiling point ]
254.38°C (rough estimate) | [density ]
1.1708 (rough estimate) | [refractive index ]
1.5500 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Crystalline Powder | [pka]
10.65±0.18(Predicted) | [color ]
Yellow | [Odor]
Aromatic, somewhat medicinal, warm, woody -the herbaceous odour of good tenacity. | [λmax]
355 nm | [BRN ]
1239364 | [InChI]
1S/C9H10O3/c1-6(10)8-5-7(12-2)3-4-9(8)11/h3-5,11H,1-2H3 | [InChIKey]
MLIBGOFSXXWRIY-UHFFFAOYSA-N | [SMILES]
COc1ccc(O)c(c1)C(C)=O | [CAS DataBase Reference]
705-15-7(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethanone, 1-(2-hydroxy-5-methoxyphenyl)-(705-15-7) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H315-H318-H335 | [Precautionary statements ]
P261-P280-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29145090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystalline powder | [Uses]
2′-Hydroxy-5′-methoxyacetophenone is observed as a side reaction product of elbs persulphate oxidation of phenols. 2-Hydroxy-5-methoxyacetophenone is also used to prepare substituted chromanone and chromone derivatives as sirtuin 2-selective inhibitors. | [Application]
2'-Hydroxy-5'-methoxyacetophenone could find some use in perfume compositions, e. g., in artificial Oakmoss, in New Mown Hay fragrances, and in certain heavy florals. It blends well with Labdanum and with Lavender type oils, and it lends a certain amount of power and undertones to the fragrance.
| [Preparation]
reparation by reaction of dimethyl sulfate on 2,5-dihydroxyacetophenone, ? with potassium carbonate in acetone at r.t. (74%) ; ? with aqueous sodium hydroxide solution at reflux (35%). | [Synthesis Reference(s)]
Synthesis, p. 901, 1985 DOI: 10.1055/s-1985-31380 | [General Description]
2′-Hydroxy-5′-methoxyacetophenone is observed as a side reaction product of elbs persulphate oxidation of phenols. | [Synthesis]
To a suspension of 2,5-dihydroxyacetophenone (100 mg, 0.66 mmol) and potassium carbonate (95 mg, 0.69 mmol) was added dimethyl sulfate (87 mg, 0.69 mmol) and the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was filtered and concentrated under reduced pressure. The resulting residue was treated with 2N NaOH aqueous solution and subsequently extracted with EtOAc. The organic layers were combined, washed with saturated saline, dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with hexane-EtOAc (10:1, v/v) as eluent to afford 2'-hydroxy-5'-methoxyacetophenone in 40% yield as a colorless oil.1H NMR (400 MHz, CDCl3) δ: 11.9 (s, 1H), 7.18 (d, J = 2.8 Hz, 1H), 7.12 (dd, J = 8.8, 2.8 Hz, 1H), 6.93 (d, J = 8.8 Hz, 1H), 3.81 (s, 3H), 2.63 (s, 3H). | [References]
[1] Journal of the Chinese Chemical Society, 2004, vol. 51, # 6, p. 1389 - 1394
[2] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1143 - 1152
[3] Journal fuer Praktische Chemie (Leipzig), 1937, vol. <2> 149, p. 324,325
[4] Journal of the Indian Chemical Society, 1990, vol. 67, # 6, p. 478 - 481
[5] European Journal of Medicinal Chemistry, 2009, vol. 44, # 6, p. 2552 - 2562 |
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