p-Trifluoromethoxy phenol

Product Namep-Trifluoromethoxy phenol
CAS828-27-3
MFC7H5F3O2
MW178.11
EINECS212-583-0
MOL File828-27-3.mol

Chemical Properties

Melting point	17-18°C
Boiling point	92 °C25 mm Hg(lit.)
Density	1.375 g/mL at 25 °C(lit.)
refractive index	n20/D 1.447(lit.)
Flash point	187 °F
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	Chloroform, Methanol
pka	9.30±0.13(Predicted)
form	Liquid
Specific Gravity	1.375
color	Clear brown
BRN	1945934
InChI	1S/C7H5F3O2/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4,11H
InChIKey	NWVVVBRKAWDGAB-UHFFFAOYSA-N
SMILES	Oc1ccc(OC(F)(F)F)cc1
CAS DataBase Reference	828-27-3(CAS DataBase Reference)
NIST Chemistry Reference	Phenol, 4-(trifluoromethoxy)-(828-27-3)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	20/21/22-36/37/38
Safety Statements	26-27-36/37/39
RIDADR	2927
WGK Germany	2
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29095090
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 3 Oral Aquatic Chronic 3 Eye Dam. 1 Skin Corr. 1B

MSDS

Provider	Language
p-Trifluoromethoxy phenol	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Uses

4-(Trifluoromethoxy)phenol is used as a reactant in the preparation of 1-aryloxyethyl piperazine derivatives as Kv1.5 potassium channel inhibitors.

Chemical Properties

clear brown liquid

Uses

4-(Trifluoromethoxy)phenol was employed in the catalytic enantioselective synthesis of esters.

Uses

Intermediates of Liquid Crystals

Uses

4-(Trifluoromethoxy)phenol is used as a reactant in the preparation of 1-aryloxyethyl piperazine derivatives as Kv1.5 potassium channel inhibitors.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 1097, 1982 DOI: 10.1021/jm00351a018

Synthesis

139301-27-2

828-27-3

General procedure for the synthesis of 4-trifluoromethoxyphenol from 4-trifluoromethoxyphenylboronic acid: In an atypical method, a flask containing 4-trifluoromethoxyphenylboronic acid (100 mg, 0.82 mmol) was taken to which 10 mol% of iron(III) oxide photocatalyst (13.1 mg) and tetrahydrofuran (2 ml) were added. The reaction mixture was stirred in a normal open flask under diffuse sunlight until complete consumption of the feedstock was shown by thin layer chromatography (TLC) detection. Upon completion of the reaction, the reaction was quenched with water and filtered to remove the catalyst. The filtrate was concentrated under vacuum. The crude product was purified by column chromatography on silica gel (100-200 mesh) with an eluent of 15:1 ethyl acetate/hexane, resulting in 73.2 mg (95% yield) of pure crystalline 4-trifluoromethoxyphenol.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 4, p. 811 - 814
[2] Tetrahedron Letters, 2015, vol. 55, # 4, p. 811 - 814
[3] Synthesis (Germany), 2014, vol. 46, # 3, p. 295 - 300

p-Trifluoromethoxy phenol

Chemical Properties

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MSDS

Usage And Synthesis

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