3-CHLOROPHENETHYLALCOHOL Chemical Properties

Boiling point:

135-137 °C/13 mmHg (lit.)

Density 

1.181 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.549(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

14.76±0.10(Predicted)

Specific Gravity

1.157

color 

Clear colorless to very slightly yellow

BRN 

2042059

InChI

InChI=1S/C8H9ClO/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6,10H,4-5H2

InChIKey

NDWAVJKRSASRPH-UHFFFAOYSA-N

SMILES

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

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

29052900

MSDS

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

3-CHLOROPHENETHYLALCOHOL Usage And Synthesis

Chemical Properties

clear colorless to very slightly yellow liquid

General Description

3-Chlorophenethyl alcohol undergoes coupling reaction with dibutylamine.

Synthesis

Example 86A Synthesis of 2-(3-chlorophenyl)ethanol: To a solution of 2-(3-chlorophenyl)acetic acid (11.4 g, 66.7 mmol) dissolved in 150 mL of THF was added LiAlH4 (3.04 g, 80.0 mmol) in batches at 0 °C. The reaction mixture was gradually warmed up to room temperature and stirred continuously under nitrogen protection for 2 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 2N NaOH solution (30 mL), followed by extraction with ethyl acetate (2 x 150 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (silica gel as stationary phase, petroleum ether/ethyl acetate = 50:1 to 10:1 gradient elution) to give 4.96 g of the target product, 3-chlorophenethyl alcohol, as a colorless oil. The yield was 55%.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 756 - 760
[2] Patent: US2013/131036, 2013, A1. Location in patent: Paragraph 1585; 1586
[3] Patent: WO2013/62966, 2013, A2. Location in patent: Paragraph 112; 113
[4] Helvetica Chimica Acta, 1973, vol. 56, p. 2460 - 2479
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 228 - 246

3-CHLOROPHENETHYLALCOHOL(5182-44-5)Related Product Information

• 3-CHLOROPHENETHYLALCOHOL
• Phenethyl alcohol
• α-Amino-2'-chlorophenylethanol
• 2-CHLOROPHENETHYLALCOHOL 98%,2-CHLOROPHENETHYLALCOHOL
• 4-CHLOROPHENETHYLALCOHOL,p-chlorophenethylalcoho
• 3,4-DICHLOROPHENETHYL ALCOHOL
• 1-(3-Chlorophenyl)-1-ethanol
• α-(p-chlorophenyl)ethyl alcohol
• 2,6-DICHLOROPHENETHYLALCOHOL
• O-CHLOROPHENETHYLALCOHOL
• 2,4-DICHLOROPHENETHYL ALCOHOL