1-(2-Chloro-6-hydroxyphenyl)ethanone

1-(2-Chloro-6-hydroxyphenyl)ethanone Property

Boiling point:

225.4±20.0 °C(Predicted)

Density 

1.298±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

9.20±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C8H7ClO2/c1-5(10)8-6(9)3-2-4-7(8)11/h2-4,11H,1H3

InChIKey

RUSSVKYJPIADHS-UHFFFAOYSA-N

SMILES

C(=O)(C1=C(O)C=CC=C1Cl)C

Safety

HS Code 

2914500090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-(2-Chloro-6-hydroxyphenyl)ethanone Chemical Properties,Usage,Production

Uses

1-(2-Chloro-6-hydroxyphenyl)ethanone is used for synthesis and structure-activity relationship of novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors.

Preparation

Preparation by diazotization of 2-amino-6-chloro-acetophenone, followed by hydrolysis of the obtained diazonium salt (55%).

Synthesis

1. To a solution of 2-chloro-6-hydroxybenzonitrile (614 mg, 4 mmol) in tetrahydrofuran (THF, 10 mL) under argon protection is slowly added a solution of methylmagnesium bromide in toluene/THF (3:1, 1.4 M, 6.4 mL, 9 mmol). Note: Gas escapes during the reaction. 2. Stir the reaction mixture at room temperature until the escape of gas ceases. 3. Transfer the reaction mixture to a sealed tube and stir overnight at 65°C. 4. 4. upon completion of the reaction, the reaction is quenched with water and acidified with aqueous hydrochloric acid. 5. The organic layer containing 1-(2-chloro-6-hydroxyphenyl)ethanone was extracted with dichloromethane (DCM). 6. The product was purified by column chromatography using dichloromethane/hexane (1:1) as eluent to afford 1-(2-chloro-6-hydroxyphenyl)ethanone (100 mg, 15% yield).

References

[1] Patent: WO2010/56631, 2010, A1. Location in patent: Page/Page column 132-134