1,3,5-Tris(trifluoromethyl)benzene Chemical Properties

Melting point:

9.0 °C

Boiling point:

120 °C/750 mmHg (lit.)

Density 

1.514 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.359(lit.)

Flash point:

110 °F

solubility 

Chloroform, Ethyl Acetate (Sparingly)

form 

clear liquid

color 

Colorless to Almost colorless

Stability:

Volatile

InChI

InChI=1S/C9H3F9/c10-7(11,12)4-1-5(8(13,14)15)3-6(2-4)9(16,17)18/h1-3H

InChIKey

ZMAUHKSOLPYPDB-UHFFFAOYSA-N

SMILES

C1(C(F)(F)F)=CC(C(F)(F)F)=CC(C(F)(F)F)=C1

CAS DataBase Reference

729-81-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Flammable

HazardClass 

3

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:1,3,5-Tris(trifluoromethyl)benzene
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1,3,5-Tris(trifluoromethyl)benzene Usage And Synthesis

Uses

1,3,5-tris(trifluoromethyl)benzene was used as a starting material in the synthesis of bis(2,4,6-tris(trifluoromethyl)phenyl)chloropnictines.
It may be used as a starting material in the synthesis of 2,4,6-tris(trifluoromethyl)benzoic acid by reacting with n-butyllithium and carbon dioxide and in the synthesis of lithio derivative, via direct metalation with n-butyllithium.

General Description

1,3,5-tris(trifluoromethyl)benzene is a tri-substituted benzene. It has been synthesized by reacting benzene-1,3,5-tricarboxylic acid with SF₄. Reports suggest that 1,3,5-tris(trifluoromethyl)benzene is a nonanesthetics and shows convulsant properties. Its vapor absorption spectra and corresponding solution spectra has been investigated. Its reaction with methyl lithium has been analyzed using semiempirical reaction modelling.

Structure and conformation

The principal structural parameters rh1(∠h1) determined by GED are (bond lengths in Angstroms and bond angles in degrees with 3σ in parentheses): r(C C)=1.392(4), r(C?C)=1.512(4), r(C?F)av=1.346(2), ∠C–C(CF3)– C=120.9(2), ∠C–C(H)–C=119.1(2), ∠(C–C–F)av=111.6(2). The structure of the carbon ring deviates from a regular hexagon due to the σ-electronegative effect of the CF3 groups. The geometric parameters of the trifluoromethyl groups deviate considerably from regular tetrahedron arrangement[1].

References

[1] Inna N. Kolesnikova . “Molecular structure and conformation of 1,3,5-tris(trifluoromethyl)-benzene as studied by gas-phase electron diffraction and quantum chemical calculations.” Journal of Molecular Structure 1074 (2014): Pages 196-200.

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