2'-Hydroxy-5'-methoxyacetophenone Chemical Properties

Melting point:

52 °C(lit.)

Boiling point:

254.38°C (rough estimate)

Density 

1.1708 (rough estimate)

refractive index 

1.5500 (estimate)

Flash point:

>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

InChIKey

MLIBGOFSXXWRIY-UHFFFAOYSA-N

CAS DataBase Reference

705-15-7(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2-hydroxy-5-methoxyphenyl)-(705-15-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-37/39-36/37/39-22

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2'-Hydroxy-5'-methoxyacetophenone Usage And Synthesis

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

2'-Hydroxy-5'-methoxyacetophenone(705-15-7)Related Product Information

• 4'-Hydroxyacetophenone
• PIPERACETAZINE (250 MG)
• 2'-Methoxyacetophenone
• CHLOROPHOSPHONAZO III
• 3-Methoxyacetophenone
• 2',4'-Dichloroacetophenone
• 3-Aminoacetophenone
• 3',5'-Dimethoxyacetophenone
• 4-Nitroacetophenone
• 4'-Methoxyacetophenone
• 3,4-Dimethoxyacetophenone
• 2-HYDROXYACETOPHENONE
• Acetophenone
• 2'-Hydroxyacetophenone
• 3-Nitroacetophenone
• 2-BROMO-2',5'-DIMETHOXYACETOPHENONE
• EUPATORIN-5-METHYL ETHER
• 4',6,7-Trimethoxyisoflavone