ChemicalBook CAS DataBase List 705-15-7

705-15-7

Name	2'-Hydroxy-5'-methoxyacetophenone
CAS	705-15-7
EINECS(EC#)	211-882-3
Molecular Formula	C9H10O3
MDL Number	MFCD00008731
Molecular Weight	166.17
MOL File	705-15-7.mol

Chemical Properties

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

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 . less more
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 . less more
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

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

77-78-1

490-78-8

705-15-7

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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