2'-Hydroxy-6'-methoxyacetophenone

Product Name2'-Hydroxy-6'-methoxyacetophenone
CAS703-23-1
MFC9H10O3
MW166.17
EINECS211-872-9
MOL File703-23-1.mol

Chemical Properties

Melting point	58-60 °C(lit.)
Boiling point	141 °C16 mm Hg(lit.)
Density	1.158
refractive index	1.5500 (estimate)
Flash point	141°C/16mm
storage temp.	Sealed in dry,Room Temperature
pka	9.79±0.10(Predicted)
form	solid
color	Light yellow to yellow
BRN	1869049
InChI	1S/C9H10O3/c1-6(10)9-7(11)4-3-5-8(9)12-2/h3-5,11H,1-2H3
InChIKey	UENLHUMCIOWYQN-UHFFFAOYSA-N
SMILES	COc1cccc(O)c1C(C)=O
LogP	2.390 (est)
CAS DataBase Reference	703-23-1(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
Hazard Note	Irritant
TSCA	N
HS Code	29145090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

Yellow crystalline powder

Uses

2′-Hydroxy-6′-methoxyacetophenone was used as starting material in the synthesis of 5-methoxyflavaone. It was also used in synthesis of 5,6-dihydroxyflavone.

Uses

2''-Hydroxy-6''-methoxyacetophenone is useful in the synthesis of an aminopyrazole compound which is used to treat cancer and inhibits Chk1. 2''-Hydroxy-6''-methoxyacetophenone is also used to prepare 5,4''-disubstituted flavones, predicted androgen receptor antagonists and naphthopyrazolyl carbothioamides which are anticancer agents.

Preparation

Preparation by reaction of methyl iodide on 2,6-dihydroxyacetophenone with potassium carbonate in boiling acetone (56%).

Definition

ChEBI: 2'-Hydroxy-6'-methoxyacetophenone is an aromatic ketone.

General Description

An organometallic synthetic route to 2′-hydroxy-6′-methoxyacetophenone was reported.

Synthesis

127-19-5

3-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE,95.0+%(GC)

217813-03-1

15799-79-8

703-23-1

Ethanone, 1-[2-(dimethylamino)-6-methoxyphenyl]-

1220955-97-4

Under argon protection, TBAF (157 mg, 0.60 mmol) was dissolved in DMA (1.2 mL), followed by addition of a solution of 3-methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (53 μL, 0.20 mmol) in DMA (0.8 mL). The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (0.1 mL). The reaction mixture was concentrated under reduced pressure and the residue was purified by fast silica gel column chromatography (eluent: ethyl acetate/hexane = 1/20 to 1/8 containing 2% dichloromethane) to afford 2-hydroxy-6-methoxyacetophenone (10, 11.3 mg, 34%), 2-(N,N-dimethyl)amino-6-methoxyacetophenone (11, 3.8 mg, 10%) and 3-methoxy- N,N-dimethylaniline (12, 1.3 mg, 5%). 2-Hydroxy-6-methoxyacetophenone (10): colorless crystals, melting point 57-57.5 °C (ethyl acetate/hexane). IR (KBr) νmax 3110, 3009, 2947, 1623, 1594, 1459 cm1.1 1H NMR (CDCl3) δ 13.23 (1H, s), 7.33 (1H, t, J = 8.0 Hz ), 6.56 (1H, dd, J = 8.0, 1.0 Hz), 6.39 (1H, dd, J = 8.0, 1.0 Hz), 3.90 (3H, s), 2.67 (3H, s).13C NMR (CDCl3) δ 205.1, 164.6, 161.5, 136.0, 111.3, 110.7, 101.1, 55.6, 33.7.MS (EI+) m/z 83 (100), 166 (M+, 3).HRMS (EI+) calculated value of C9H10O3 (M+) 166.0624, measured value 166.0646. 2-(N,N-dimethyl)amino-6-methoxyacetophenone (11): colorless oil. ir (CHCl3) νmax 2942, 1702, 1577, 1468 cm1. 1H NMR (CDCl3) δ 7.23 (1H, br t, J = 8.0 Hz), 6.67 (1H, br d, J = 8.0 Hz), 6.56 ( 1H, br d, J = 8.0 Hz), 3.78 (3H, s), 2.72 (6H, s), 2.50 (3H, s).13C NMR (CDCl3) δ 205.2, 156.2, 151.8, 130.2, 125.3, 111.0, 104.7, 55.8, 44.8, 31.8.MS (EI+) m/z 83 (100), 193 (M+, 0.4). HRMS (EI+) calculated value C11H15NO2 (M+) 193.1097, measured value 193.1121. 3-Methoxy-N,N-dimethylaniline (12): colorless oily substance. ir (KBr) νmax 2955, 1610, 1493, 1465 cm1. 1H NMR (CDCl3) δ 7.15 (1H, t, J = 8.0 Hz), 6.36 (1H, dd, J = 8.0, 2.5 Hz), 6.31-6.27 (2H, m), 3.80 (3H, s), 2.94 (6H, s).13C NMR (CDCl3) δ 160.6, 151.9, 129.7, 105.7, 101.3, 99.1, 55.1, 40.6.MS (EI+) m/z 83 (100), 151 (M+, 0.4).HRMS (EI+) calculated values C9H14NO (M++H+) 152.1070, measured value 152.1055.

References

[1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189

Preparation Products And Raw materials

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