2-Chloro-3',4'-dihydroxyacetophenone Chemical Properties

Melting point:

174-176 °C(lit.)

Boiling point:

418.7±35.0 °C(Predicted)

Density 

1.444±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in DMSO, methanol.

pka

7.59±0.20(Predicted)

form 

powder

color 

White to Pale Beige

BRN 

2092660

InChI

InChI=1S/C8H7ClO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,10-11H,4H2

InChIKey

LWTJEJCZJFZKEL-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(O)C(O)=C1)CCl

CAS DataBase Reference

99-40-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

29252900

MSDS

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

2-Chloro-3',4'-dihydroxyacetophenone Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

2-Chloro-3',4'-dihydroxyacetophenone is used as a styptic adrenobazone, quasi adrenaline drug gasp spirit of intermediates.

Definition

ChEBI: 2-chloro-3',4'-dihydroxyacetophenone is an alpha-chloroketone, a member of acetophenones and an aromatic ketone.

Synthesis

Anhydrous aluminum trichloride (6.0 g, 45 mmol) was slowly added to the cooled 1,2-dichloroethane (20 mL) solution at 5-10 °C and stirred for 30 min keeping the temperature at 5-10 °C. Subsequently, catechol (1) (2.0 g, 18.1 mmol) was added to the reaction mixture in batches over a period of 10 minutes and stirring was continued for 20 minutes. Chloroacetyl chloride (2.2 g, 19.3 mmol) was added dropwise to the reaction system at the same temperature. The reaction system was then warmed up to room temperature with continuous stirring for 20 hours. Upon completion of the reaction, the reaction was carefully quenched with dilute hydrochloric acid solution (40 mL) at 5-10 °C and stirred at room temperature for 2-3 hours. The solid product was collected by filtration and washed with water. The wet solid was suspended in dilute acetic acid and heated until completely dissolved. Activated charcoal (0.1 g) was added to the clarified solution to decolorize it, stirred for 30 minutes and then hot filtered. The filtrate was cooled to precipitate a solid, filtered, washed with water and dried to give the target product 2-chloro-1-(3,4-dihydroxyphenyl)ethanone (2). Yield: 2.5 g, 74% yield; melting point 175-177 °C.

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 293 - 307
[2] Patent: WO2008/107109, 2008, A1. Location in patent: Page/Page column 4-5
[3] Patent: WO2018/127806, 2018, A1. Location in patent: Page/Page column 8
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 858
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1893, vol. 25, p. 154

2-Chloro-3',4'-dihydroxyacetophenone(99-40-1)Related Product Information

• 2-Chloroacetophenone
• Pyrocatechol Violet
• Catechol
• 2,4-Dichloro-5-fluoroacetophenone
• Epichlorohydrin
• Acetophenone
• 2-HYDROXYACETOPHENONE
• 4'-Hydroxyacetophenone
• 3-Aminoacetophenone
• 4-Nitroacetophenone
• 4'-Methoxyacetophenone
• 4'-Chloroacetophenone
• 3-Nitroacetophenone
• 2',4'-Dichloroacetophenone
• 2,4-Dihydroxyacetophenone
• 3,4-Dihydroxyacetophenone
• 6-CHLOROACETYL-1 4-BENZODIOXANE 97
• Chloroacetic acid