Tris(hydroxymethyl)phosphine

Tris(hydroxymethyl)phosphine (THP) is a chemical compound with the formula P(CH2OH)3. It is a colorless liquid that is soluble in water and polar organic solvents. THP is a common ligand in coordination chemistry and a building block for other phosphorus compounds.

Structure and Bonding

Tris(hydroxymethyl)phosphine is a phosphine with three hydroxymethyl groups attached to the phosphorus atom. The P-C bond length is approximately 1.84 Å, and the C-O bond length is approximately 1.43 Å. The P-C-C and C-C-O bond angles are approximately 112° and 109.5°, respectively.

Synthesis

Tris(hydroxymethyl)phosphine can be synthesized by the reaction of phosphorus trichloride with formaldehyde and hydrochloric acid. The reaction proceeds via a nucleophilic substitution mechanism.

Applications

Tris(hydroxymethyl)phosphine is used as a ligand in coordination chemistry. It forms complexes with many transition metals, including copper, nickel, and palladium. These complexes have been studied for their potential applications in catalysis and material science.

Safety

Tris(hydroxymethyl)phosphine is a flammable liquid. It can cause burns and eye damage. It should be handled with care, using appropriate personal protective equipment.

See Also

• Phosphine
• Hydroxymethyl group
• Coordination chemistry
• Nucleophilic substitution