4-Phenoxybutyl bromide Chemical Properties

Melting point:

41-43 °C(lit.)

Boiling point:

153-156 °C18 mm Hg(lit.)

Density 

1.3236 (rough estimate)

refractive index 

1.5310 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to lump

color 

White to Almost white

Water Solubility 

Insoluble in water.

BRN 

2044374

InChI

InChI=1S/C10H13BrO/c11-8-4-5-9-12-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2

InChIKey

QBLISOIWPZSVIK-UHFFFAOYSA-N

SMILES

C1(OCCCCBr)=CC=CC=C1

CAS DataBase Reference

1200-03-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, (4-bromobutoxy)-(1200-03-9)

EPA Substance Registry System

Benzene, (4-bromobutoxy)- (1200-03-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29093038

MSDS

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4-Phenoxybutyl bromide Usage And Synthesis

Chemical Properties

OFF-WHITE CRYSTALLINE MASS

Uses

(4-Bromobutoxy)benzene is used to produce 5-phenoxy-valeric acid with carbon dioxide and reagent Mg.

Synthesis

General procedure: In a 500 mL round-bottomed flask, phenol (50 g, 1 eq.), 1,4-dibromobutane (137.7 g, 1.2 eq.), and potassium carbonate (110.5 g, 1.5 eq.), which has been baked at 70 °C for about 2 hours and milled, are added sequentially at room temperature. Potassium iodide (5.5 g, based on 5% of the mass of potassium carbonate) was added under mechanical stirring. The reaction mixture was then warmed up to 80 °C and the reaction was continued at this temperature for 4 to 6 hours, during which the reaction progress was monitored by liquid chromatography. Upon completion of the reaction, the reaction solution was cooled to room temperature and filtered. The filtrates were combined at 40-45 °C and concentrated under reduced pressure at 0.09-0.1 MPa. The resulting crude product had a purity of 90.6% and was subsequently distilled under reduced pressure at 120-130 °C to collect the fractions.The recovery of 1,4-dibromobutane was 64.1% and the net yield of the target product, 4-phenoxybromobutane, was 96.1%.

References

[1] Patent: CN104447220, 2016, B. Location in patent: Paragraph 0024-0026
[2] Archiv der Pharmazie, 2009, vol. 342, # 12, p. 732 - 739
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1244 - 1251
[4] Tetrahedron Letters, 2010, vol. 51, # 35, p. 4612 - 4616
[5] Chemical Communications, 2014, vol. 50, # 39, p. 5017 - 5019

4-Phenoxybutyl bromide(1200-03-9)Related Product Information

• PHENOXY RESIN
• 1-Bromobutane
• 4-PHENOXYBUTYL BROMIDE, (4-BROMOBUTYL PHENYL ETHER; 1-BROMO-4