Triphenylborane

Triphenylborane (TPB) is a chemical compound with the formula (C6H5)3B, often abbreviated as Ph3B. It is a colorless solid that is soluble in organic solvents. It is a common reagent in organic chemistry for the synthesis of various organic compounds.

Structure and Bonding

Triphenylborane is a planar molecule. The boron atom is sp2 hybridized, resulting in a trigonal planar geometry. The boron atom is bonded to three phenyl groups, which are aromatic hydrocarbon rings. The boron atom has an empty p-orbital which can accept a pair of electrons, making triphenylborane a Lewis acid.

Preparation

Triphenylborane can be prepared by the reaction of phenylmagnesium bromide with boron trifluoride etherate. The reaction proceeds via a Grignard reagent, which is a powerful nucleophile and base.

Uses

Triphenylborane is used as a reagent in organic chemistry. It is used as a catalyst in the hydroboration-oxidation reaction, which is a method for the conversion of alkenes to alcohols. It is also used as a reducing agent in the reduction of carboxylic acids to alcohols.

Safety

Triphenylborane is a strong Lewis acid and can cause burns if it comes into contact with skin or eyes. It should be handled with care, using appropriate personal protective equipment.

See also

• Borane
• Organoboron chemistry
• Hydroboration-oxidation reaction