4-Bromophenetole

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CAS:588-96-5
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4-Bromophenetole manufacturers

  • 4-Bromophenetole
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  • CAS:588-96-5
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  • 4-Bromophenetole
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  • CAS:588-96-5
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  • 4-Bromophenetole
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  • 2021-10-30
  • CAS:588-96-5
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4-Bromophenetole Basic information
Product Name:4-Bromophenetole
Synonyms:5-[(4-bromophenyl)thio]-4-(chloromethyl)-1-methyl-3-phenylpyrazole;4-ETHOXYBROMOBENZENE;4-BROMOPHENYL ETHYL ETHER;4-BROMO PHENETOL;4-BROMOPHENETOLE;1-BROMO-4-ETHOXYBENZENE;1-BROMO-4-ETHYLOXYBENZENE;P-BROMOPHENETOLE
CAS:588-96-5
MF:C8H9BrO
MW:201.06
EINECS:209-629-7
Product Categories:alkyl bromide;Phenetole;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds
Mol File:588-96-5.mol
4-Bromophenetole Structure
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.)
Fp 218 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Methanol
form Liquid
Specific Gravity1.436
color Clear colorless to yellow
Merck 14,1428
BRN 2042066
InChIKeyWVUYYXUATWMVIT-UHFFFAOYSA-N
CAS DataBase Reference588-96-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-bromo-4-ethoxy-(588-96-5)
EPA Substance Registry SystemBenzene, 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 Information
ProviderLanguage
4-Bromophenyl ethyl ether English
SigmaAldrich English
ACROS English
ALFA English
4-Bromophenetole Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS TO YELLOWISH LIQUID
Uses4-Bromophenetole is a non-irritant used to verify ocular irritability tests.
Synthesis
4-Bromophenol

106-41-2

Iodoethane

75-03-6

4-Bromophenetole

588-96-5

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]
Tag:4-Bromophenetole(588-96-5) Related Product Information
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