3,4-DICHLOROPHENETHYL ALCOHOL

3,4-DICHLOROPHENETHYL ALCOHOL Property

Boiling point:

165 °C / 14mmHg

Density 

1.32

refractive index 

1.562-1.568

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate

form 

Liquid

color 

Clear colorless

InChI

InChI=1S/C8H8Cl2O/c9-7-2-1-6(3-4-11)5-8(7)10/h1-2,5,11H,3-4H2

InChIKey

GITOMJDYNUMCOV-UHFFFAOYSA-N

SMILES

C1(CCO)=CC=C(Cl)C(Cl)=C1

Safety

Hazard Codes 

Xi

Risk Statements 

37/38-41-51-36/37/38-20/21/22

Safety Statements 

24/25-39-26-36/37/39

RIDADR 

2810

HS Code 

29062990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

3,4-DICHLOROPHENETHYL ALCOHOL Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid

Uses

Intermediate in the synthesis of σ receptor ligands.

Synthesis

General procedure for the synthesis of 2-(3,4-dichlorophenyl)ethanol from 3,4-dichlorophenylacetic acid: 97% lithium aluminum hydride (LiAlH4, 5.54 g, 141.63 mmol) was added batchwise to an ice-bath-cooled solution of 2-(3,4-dichlorophenyl)acetic acid (19.36 g, 94.42 mmol) in tetrahydrofuran (THF, 200 mL). After the addition was completed, the reaction mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, the mixture was slowly poured into ice water (150 mL) and stirring was continued for 0.5 hours. Subsequently, THF was evaporated under reduced pressure and extracted by adding dichloromethane (DCM, 200 mL). The organic layer was separated, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5, v/v) to afford the target compound 2-(3,4-dichlorophenyl)ethanol (17.14 g, 95% yield) as a colorless oil.

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3100 - 3110
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 24, p. 5420 - 5423
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 756 - 760
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 5612