1,3-Bis(trifluoromethyl)benzene

Last updated
1,3-Bis(trifluoromethyl)benzene
1,3(CF3)2C6H4.svg
Names
Other names
α,α,α,α′,α′,α′-hexafluoro-m-xylene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.006.310 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-939-4
PubChem CID
UNII
  • InChI=1S/C8H4F6/c9-7(10,11)5-2-1-3-6(4-5)8(12,13)14/h1-4H
    Key: SJBBXFLOLUTGCW-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F
Properties
C8H4F6
Molar mass 214.110 g·mol−1
Appearancecolorless liquid
Boiling point 114–116 °C (237–241 °F; 387–389 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H226, H315, H319, H335, H411
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Bis(trifluoromethyl)benzene is an organofluorine compound with the formula C6H4(CF3)2. It is the most intensively studied of three isomers of the same formula. Like benzotrifluoride, bis(trifluoromethyl)benzene is prepared by the reaction of hydrogen fluoride with the corresponding trichloromethylbenzene compound: [1]

C6H4(CCl3)2 + 6 HF → C6H4(CF3)2 + 6 HCl

1,3-Bis(trifluoromethyl)benzene undergoes bromination to give bromo-3,5-bis(trifluoromethyl)benzene (BrC6H3(CF3)2), which is used to prepare other reagents, [2] such as the sodium salt of tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, NaBArF4. [3]

References

  1. ↑ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_349. ISBN   978-3-527-30385-4.
  2. ↑ Leazer, Johnnie L.; Cvetovich, Raymond; Tsay, Fuh-Rong; Dolling, Ulf; Vickery, Thomas; Bachert, Donald (2003). "An Improved Preparation of 3,5-Bis(trifluoromethyl)acetophenone and Safety Considerations in the Preparation of 3,5-Bis(trifluoromethyl)phenyl Grignard Reagent". The Journal of Organic Chemistry. 68 (9): 3695–3698. doi:10.1021/jo026903n.
  3. ↑ M. Brookhart; B. Grant; A. F. Volpe, Jr. (1992). "[(3,5-(CF3)2C6H3)4B]-[H(OEt2)2]+: a convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes". Organometallics. 11 (11): 3920–3922. doi:10.1021/om00059a071.
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