Methyl 3,4-dichlorophenylacetate

Methyl 3,4-dichlorophenylacetate Property

Melting point:

25-27

Boiling point:

314.25°C (rough estimate)

Density 

1.54-1.542

refractive index 

1.54-1.542

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid After Melting

color 

Clear colorless to light yellow

CAS DataBase Reference

6725-44-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37-26

Hazard Note 

Irritant

HS Code 

29163990

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.

Methyl 3,4-dichlorophenylacetate Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid

Synthesis

The general procedure for synthesizing methyl 3,4-dichlorophenylacetate from methanol and 3,4-dichlorophenylacetic acid was as follows: referring to Synthesis Example 1, methanol (59 mL, 3.0 equiv) was added to a solution of 1,2-dichloroethane (400 mL) containing 3,4-dichlorophenylacetic acid (100 g, 0.488 mol). The mixed solution was heated to 50 °C, followed by the slow dropwise addition of concentrated sulfuric acid (10 mL) over 15 min. After the dropwise addition was completed, the reaction temperature was maintained at 50°C and stirring was continued for 1.5 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and a partitioning operation was performed to separate and remove the sulfuric acid layer. The resulting organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate solution and saturated brine, followed by drying with anhydrous magnesium sulfate. After drying, the desiccant was removed by filtration and the solvent was removed by distillation, resulting in the target product methyl 3,4-dichlorophenylacetate (105 g, yield: 98%) in the form of colorless oil. The structure of the product was confirmed by 1H-NMR (300 MHz, CDCl3) with chemical shifts δ: 3.59 (s, 2H), 3.71 (s, 3H), 7.12 (dd, J = 8.4 Hz, 1.8 Hz, 1H), 7.38-7.41 (m, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2701 - 2706
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3618 - 3625
[4] Patent: US2003/225283, 2003, A1. Location in patent: Page 12-13
[5] Patent: EP2246343, 2010, A1. Location in patent: Page/Page column 10