4-Bromophenetole Chemical Properties

Melting point:

4 °C (lit.)

Boiling point:

233 °C (lit.)

Density 

1.407 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.551(lit.)

Flash point:

218 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Liquid

Specific Gravity

1.436

color 

Clear colorless to yellow

Merck 

14,1428

BRN 

2042066

InChIKey

WVUYYXUATWMVIT-UHFFFAOYSA-N

CAS DataBase Reference

588-96-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-4-ethoxy-(588-96-5)

EPA Substance Registry System

Benzene, 1-bromo-4-ethoxy- (588-96-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29093090

MSDS

• Language:English Provider:4-Bromophenyl ethyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromophenetole Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO YELLOWISH LIQUID

Uses

4-Bromophenetole is a non-irritant used to verify ocular irritability tests.

Synthesis

Step 1: Synthesis of 1-bromo-4-ethoxybenzene: Potassium carbonate (118 g) was added to a solution of 4-bromophenol (50 g) in acetone (250 mL) at room temperature and stirred for 30 min. Subsequently, iodoethane (67.6 g) was added slowly and dropwise. The reaction mixture was heated to reflux for 10 hours and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was filtered and acetone was removed using a rotary evaporator. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. Purification by silica gel column chromatography with ethyl acetate and hexane (1:7) as eluents afforded 4-bromophenetole as a colorless liquid (57 g, 98.27% yield).1H NMR (CDCl3, 300 MHz): δ 7.35 (d, J = 8.7 Hz, 2H), 6.76 (d, J = 8.7 Hz, 2H), 3.99 (q, J = 6.9 Hz, 2H), 1.40 (t, J = 6.9 Hz, 3H).

References

[1] Patent: WO2012/25857, 2012, A1. Location in patent: Page/Page column 57-58
[2] Patent: US2010/331307, 2010, A1. Location in patent: Page/Page column 18
[3] Journal of the Korean Chemical Society, 2012, vol. 56, # 6, p. 706 - 711
[4] Journal of the American Chemical Society, 1931, vol. 53, p. 1408,1409
[5] Molecular Crystals and Liquid Crystals, 2004, vol. 411, p. 93/[1135]-102/[1144]

4-Bromophenetole(588-96-5)Related Product Information

• 2-Bromofluorobenzene
• Ethylbenzene
• Bromoxynil octanoate
• 2-Bromobenzonitrile
• PETROLEUM ETHER
• 4-Bromofluorobenzene
• 3-Bromoanisole
• Dimethyl ether
• Ethylparaben
• 4-Bromobenzaldehyde
• 4'-Bromopropiophenone
• Phenetole
• Ethyl acetate
• Ethanol
• 4-Bromophenethyl alcohol
• 3-(4-Bromophenyl)propionic acid
• Ethyl acrylate
• Diethyl ether