4-Amino-3,5-dichloroacetophenone Chemical Properties

Melting point:

162-166 °C(lit.)

Boiling point:

351.5±42.0 °C(Predicted)

Density 

1.2748 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-1.72±0.10(Predicted)

color 

Light Tan to Brown

InChI

InChI=1S/C8H7Cl2NO/c1-4(12)5-2-6(9)8(11)7(10)3-5/h2-3H,11H2,1H3

InChIKey

JLPKZJDZXIKSCP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

37148-48-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29223990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-Amino-3,5-dichloroacetophenone Usage And Synthesis

Description

 4-Amino-3,5-dichloroacetophenone is an intermediate in the synthesis of the antitussive and antiasthmatic drug gramtin.

Storage

4-Amino-3,5-dichloroacetophenone should be stored in a cool, dry place in a small, well filled, well-closed container, protected from light. When a partially filled container is used, the air should be replaced by nitrogen or another inert gas.
4-Amino-3,5-dichloroacetophenone oxidizes on exposure to air, resulting in an increase in the peroxide value.

Chemical Properties

4-Amino-3,5-dichloroacetophenone is a white to light yellow crystal powder. Insoluble in cold water, slightly soluble in hot water.

Uses

4-Amino-3,5-dichloroacetophenone is used to synthesize the drug Clenbuterol. Clenbuterol is a steroid-like chemical that was initially developed to treat asthma in horses, working by relaxing the airways in the animals'lungs.

Preparation

4-Amino-3,5-dichloroacetophenone was synthesized by chlorination of 4-aminoacetophenone. Add 4-aminoacetophenone and acetic acid (80%) into the reaction pot, stir and dissolve, quickly add chlorine-containing glacial acetic acid solution, the temperature of the addition is 5°C. After the addition is completed, immediately put into ice water to precipitate, filter, and wash with water to obtain the crude product. Recrystallize with ethanol to obtain the finished product of 4-Amino-3,5-dichloroacetophenone.

Application

4-Amino-3,5-dichloroacetophenone is a compound useful in organic synthesis.

Application

4-Amino-3,5-dichloroacetophenone has active chemical properties and has been widely used in industrial chemistry, agricultural chemistry, and pharmaceutical chemistry. As a selective oxidant and green coupling reagent, it participates in a variety of oxidation reactions, rearrangement reactions, and amination reactions. In industry, it can also be used as a raw material for the synthesis of drugs, disinfectants, dyes, food seasonings, adhesives, explosives, etc.

Synthesis

To a 250 mL three-necked flask was added 8.3 g of 2,6-dichloroaniline, 50 mL of chloroform was added and stirred to disperse, then 30 g of ferric chloride was added. The temperature of the reaction system was controlled at 0 °C and 8.8 g of acetyl chloride was added dropwise. After the dropwise addition, the reaction was continued to be stirred at room temperature for 6 hours. After completion of the reaction, the reaction solution was acidified, filtration was carried out and the resulting solid was washed with water to give 9.0 g of light yellow 3,5-dichloro-4-aminoacetophenone in 88.6% yield. The purity of the product was 99.5% by HPLC.

References

[1] Patent: CN105968021, 2016, A. Location in patent: Paragraph 0168-0169

4-Amino-3,5-dichloroacetophenone(37148-48-4)Related Product Information

• 4'-Hydroxyacetophenone
• 4-Nitroacetophenone
• 3-Aminoacetophenone
• Acetyl chloride
• Dichloroacetonitrile
• 2-Aminoecetophenone
• 2-Bromoacetophenone
• 3-Nitroacetophenone
• Betaine
• Glycine
• ALTRENOGEST
• L-PICEIN
• Acetylacetone
• 4'-Methylacetophenone
• Acetophenone
• 4'-DIMETHYLAMINOACETOPHENONE
• 2',5'-Dichloroacetophenone
• 3'-DIMETHYLAMINOACETOPHENONE