2,3-Dichloroacetophenone

2,3-Dichloroacetophenone Property

Melting point:

125-127 °C

Boiling point:

67 °C

Density 

1.293

refractive index 

1.558

Flash point:

106-108°C/2mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

Colourless

BRN 

2438815

InChI

InChI=1S/C8H6Cl2O/c1-5(11)6-3-2-4-7(9)8(6)10/h2-4H,1H3

InChIKey

KMABBMYSEVZARZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

56041-57-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/38-36/37/38-22

Safety Statements 

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

Hazard Note 

Irritant

HS Code 

2914790090

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

2,3-Dichloroacetophenone Chemical Properties,Usage,Production

Chemical Properties

colorless to pale yellow liquid

Uses

2,3''-Dichloroacetophenone is used as a reagent in the synthesis of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β). Also used as a reagent in the synthesis of benzimidazolyl pyridinones as insulin-like growth factor I (IGF-1R) kinase inhibitors.

Synthesis

Method A: A hexane solution of butyl lithium (300 mL, 0.474 mol) was slowly added dropwise to 1,2-dichlorobenzene (104.58 g, 0.711 mol) dissolved in dry tetrahydrofuran (2 L) under nitrogen protection, keeping the reaction temperature at -70°C. After the dropwise addition, the reaction solution was continued to be stirred for 1 hour at -70°C. The reaction solution was then transferred to acetic anhydride (290.35 g, 2.84 mol) dissolved in anhydrous tetrahydrofuran (1 L) via double-headed needle. Subsequently, the reaction solution was transferred to acetic anhydride (290.35 g, 2.84 mol) dissolved in anhydrous tetrahydrofuran (1 L) via a double-ended needle at the same temperature. After addition, the reaction mixture was stirred at -70 °C for 1 h, followed by natural warming to room temperature. The reaction mixture was poured into ice (5 L), stirred thoroughly and allowed to stand at room temperature overnight. The aqueous phase was extracted with ether (3 x 1.5 L), and the organic phase was combined and washed sequentially with water (3 x 750 mL), saturated sodium bicarbonate solution (3 x 750 mL) and brine (1 x 750 mL). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a yellow liquid crude product. The crude product was placed in a hot water bath and the residual 1,2-dichlorobenzene and acetic anhydride were removed under high vacuum to finally obtain 2,3-dichloroacetophenone (67.2 g, 75% yield). The product was analyzed by infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and thin-layer chromatography (TLC, silica gel plate, the unfolding agent was chloroform), the product was of high purity and contained only a small amount of impurities, so it was not further purified.

References

[1] Patent: US5912345, 1999, A
[2] Patent: US5925755, 1999, A