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2-Fluorobenzotrifluoride

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CAS:392-85-8
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CAS:392-85-8
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2-Fluorobenzotrifluoride Basic information
Product Name:2-Fluorobenzotrifluoride
Synonyms:2-FLUOROBENZOTRIFLUORIDE;1-FLUORO-2-(TRIFLUOROMETHYL)BENZENE;ALPHA,ALPHA,ALPHA,2-TETRAFLUOROTOLUENE;O-FLUOROBENZOTRIFLUORIDE;o-fluorotrifluorotoluene;2-Fluorobezotrifluoride;1-Fluoro-2-(trifluoromethyl)benzene alpha,alpha,alpha,2-Tetrafluorotoluene;Orthofluorine three fluorine toluene
CAS:392-85-8
MF:C7H4F4
MW:164.1
EINECS:206-880-4
Product Categories:Aromatic Hydrocarbons (substituted) & Derivatives;Benzene series;Miscellaneous;Trifluoromethylbenzene serise;bc0001
Mol File:392-85-8.mol
2-Fluorobenzotrifluoride Structure
2-Fluorobenzotrifluoride Chemical Properties
Melting point -49°C
Boiling point 114-115 °C750 mm Hg(lit.)
density 1.293 g/mL at 25 °C(lit.)
refractive index n20/D 1.406(lit.)
Fp 64 °F
storage temp. Sealed in dry,2-8°C
form clear liquid
color Colorless to Light yellow to Light orange
Specific Gravity1.31
BRN 2046638
InChIInChI=1S/C7H4F4/c8-6-4-2-1-3-5(6)7(9,10)11/h1-4H
InChIKeyBGVGHYOIWIALFF-UHFFFAOYSA-N
SMILESC1(F)=CC=CC=C1C(F)(F)F
CAS DataBase Reference392-85-8(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-fluoro-2-(trifluoromethyl)-(392-85-8)
EPA Substance Registry SystemBenzene, 1-fluoro-2-(trifluoromethyl)- (392-85-8)
Safety Information
Hazard Codes F,Xi
Risk Statements 11-36/37/38
Safety Statements 16-26-33-24/25-7/9
RIDADR UN 1993 3/PG 2
WGK Germany 3
Hazard Note Flammable/Irritant
TSCA TSCA listed
HazardClass 3
PackingGroup II
HS Code 29039990
Storage Class3 - Flammable liquids
Hazard ClassificationsEye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2-Fluorobenzotrifluoride English
SigmaAldrich English
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2-Fluorobenzotrifluoride Usage And Synthesis
Chemical Propertiesclear colorless liquid
Uses2-Fluorobenzotrifluoride was used in the synthesis of 2,2′-bis(trifluoromethylphenoxy)biphenyl via nucleophilic aromatic substitution reaction with 2,2′-biphenol.
Synthesis
Benzotrifluoride

98-08-8

4-Fluorobenzotrifluoride

402-44-8

3-Fluorobenzotrifluoride

401-80-9

2-Fluorobenzotrifluoride

392-85-8

2,5-DIFLUOROBENZOTRIFLUORIDE

393-38-4

General procedure: In a FEP or PFA reactor equipped with a PTFE-lined magnetic stirring bar and connected to a gas scrubber bottle, substituted benzene (0.95-1.10 mmol), 1,1,1,3,3-pentafluorobutane (2 ml per ml C6H5R), and BF3-Et2O (1.3-1.5 mmol per mmol C6H5R) were added. The mixture was stirred at 0-5 °C (ice bath) for 10-15 min, followed by batchwise addition of XeF2 (1.2-1.3 mmol per mmol C6H5R). After each addition, the mixture was stirred at 22-25 °C for 3-5 min and cooled again. After the addition was completed, the dark solution was continued to be stirred at 22-25 °C for 15-30 min. Subsequently, 10% aqueous KHCO3 solution was added and the upper organic layer was separated and filtered through a short column equipped with silica gel (40-60 μm) and finally dried with magnesium sulfate. The solution was analyzed by 19F NMR and GC/MS. The major products are listed in the table and other products are as follows (GC/MS data).

References[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1400 - 1407
[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1412 - 1419,8
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