3-Phenoxypropyl bromide Chemical Properties

Melting point:

10-11 °C (lit.)

Boiling point:

130-134 °C/14 mmHg (lit.)

Density 

1.365 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.546(lit.)

Flash point:

228 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO (Slightly), Methanol (Slightly)

form 

Liquid

Specific Gravity

1.365

color 

Clear slightly brown

BRN 

508978

InChIKey

NIDWUZTTXGJFNN-UHFFFAOYSA-N

LogP

3.290 (est)

CAS DataBase Reference

588-63-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, (3-bromopropoxy)-(588-63-6)

EPA Substance Registry System

Benzene, (3-bromopropoxy)- (588-63-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29093090

MSDS

• Language:English Provider:3-Bromopropyl phenyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Phenoxypropyl bromide Usage And Synthesis

Chemical Properties

lightbrown liquid

Uses

3-Phenoxypropyl Bromide is a reagent used in the synthesis of damidines in the study of myotonic dystrophy. Also used in thepreparation pf phenoxyalkylbenzimidazoles with antitubercular activity.

Synthesis

General procedure for the synthesis of 3-phenoxybromopropane (26) from 1,3-dibromopropane and phenol: Phenol (1.0 g, 10.6 mmol) was dissolved in acetone (20 ml). To this solution anhydrous potassium carbonate (7.34 g, 53.1 mmol) and 1,3-dibromopropane (8.58 g, 42.5 mmol) were added. The reaction mixture was refluxed in an oil bath for 12 hours. Upon completion of the reaction, the potassium carbonate was removed by filtration and the solvent was subsequently removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent: ethyl acetate:hexane = 3:7) to give the final target product 26 (2.05 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.24 (m, 2H), 3.54 (t, J=6.4 Hz, 2H), 4.03 (t, J=5.8 Hz, 2H), 6.86 (m, 3H), 7.21 (m, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1244 - 1251
[2] Chemical Communications, 2012, vol. 48, # 52, p. 6517 - 6519
[3] Patent: WO2013/163321, 2013, A1. Location in patent: Paragraph 000181
[4] Dyes and Pigments, 2010, vol. 84, # 2, p. 183 - 189
[5] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 292 - 299

3-Phenoxypropyl bromide(588-63-6)Related Product Information

• Anisole
• (Trifluoromethoxy)benzene
• Tetrabromobisphenol A bis(dibromopropyl ether)
• 2-Butoxyethanol
• Triton X-100
• 2-Phenoxyethanol
• Decabromodiphenyl oxide
• Ethylbenzene
• 1-Bromopropane
• Glycidyl phenyl ether
• Rocuronium bromide
• 2-Bromopropane
• Allyl glycidyl ether
• Ethidium bromide
• p-Anisaldehyde
• Allyl bromide
• PHENYL VALERATE
• 1-Bromo-3-methoxypropane