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1,3-Bis(trifluoromethyl)benzene undergoes regioselective metalation and subsequent carboxylation at position 2 to give 2,6-bis(trifluoromethyl)benzoic acid. a convenient, selective synthesis of bis[2,4-bis(trifluoromethyl)phenyl]phosphane derivatives with 1,3-bis(trifluoromethyl)benzene as starting material.
Aeberli P,; Houlihan WJ. The Metalation of 1, 3-Bis (trifluoromethyl) benzene by n butyllithium.. J. Organomet. Chem. 1974, 64 (3), 321-25.
Berthold Hoge Dr.,; Boris Kurscheid,; Sebastian Peuker,; Wieland Tyrra,; Hendrik T. M. Fischer. A Convenient, Selective Synthesis of Bis[2,4-bis(trifluoromethyl)phenyl]phosphane Derivatives Starting from 1,3-Bis(trifluoromethyl)benzene . Zeitschrift für anorganische und allgemeine Chemie. 2007, 633 (10) ,679-1685 pg no.
Metallation with n-BuLi in diethyl ether is unselective, giving, on quenching with CO2, a mixture of 2,4- and 2,6-bis(trifluoromethyl)benzoic acids: J. Organomet. Chem., 67, 321 (1974). The superbasic n-BuLi/KO-t-Bu combination leads to almost exclusive 2-metallation, allowing the 2,6-bis(trifluoromethyl) acid to be isolated in 78% yield. In contrast, a combination of sec-BuLi and N,N,N',N',N'-pentamethyldiethylenetriamine leads to the 2,4-bis(trifluoromethyl) acid as the main product: Synlett, 747 (1990).
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant