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Hexamethylenetetramine is used as a formylation agent in the synthesis and as a precipitating agent. It is also used in the production of phenolic resins and its moulding compounds, which finds application as binders in fire proof materials, brake and clutch linings. It is involved in the preparation of 5-tert-butyl-2-hydroxy-isophthalaldehyde. It is useful for the treatment of urinary tract infection. Further, it is used in the Duff reaction, Sommelet reaction and in the Delepine reaction.
For a review of applications in organic synthesis, see: Synthesis, 161 (1979).
Benzylic halides form quaternary salts with hexamine which undergo oxidation during hydrolysis to give aldehydes (Sommelet reaction): Org. React., 8, 197 (1954); Org. Synth. Coll., 3, 811 (1955); 4, 690, 918 (1963). Benzylamines can also be converted to benzaldehydes; see e.g.: Org. Synth. Coll., 5, 668 (1973).
The reaction can also be carried out to give the primary amine on hydrolysis (Delepine reaction). For conversion of allylic halides to amines, see, e.g.: Org. Synth. Coll., 5, 121 (1973); 9, 666 (1998).
Formylation of arylamines and phenols in the presence of acid to give aldehydes (Duff reaction) generally gives low yields: J. Chem. Soc., 547 (1941); Org. Synth. Coll., 4, 866 (1963). In TFA, formylation of aromatic hydrocarbons occurs in good yield with para-selectivity: J. Org. Chem., 37, 3972 (1972). Careful control of reaction conditions enables 4-substituted phenols in TFA to be converted to either 2-formyl or 2,6-diformyl derivatives: Synthesis, 1029 (1998).
Can be used as a Mannich reagent, e.g. for the ɑ-methylenation of ketones: Synth. Commun., 26, 1775 (1996). For example with reaction scheme, see Propiophenone, A15140.
Opasanont, B.; Van, K. T.; Kuba, A. G.; Choudhury, K. R.; Baxter, J. B. Adherent and Conformal Zn(S,O,OH) Thin Films by Rapid Chemical Bath Deposition with Hexamethylenetetramine Additive. ACS Appl. Mater. Interfaces 2015, 7 (21), 11516-11525.
Durá, G.; Carrión, M. C.; Jalón, F. A.; Manzano, B. R.; Rodri?guez, A. M.; Mereiter, K. Robust 2D Coordination Networks from a Two-Step Assembly Process with Predesigned Silver Cyclic Dimers and Hexamethylenetetramine. Cryst. Growth Des. 2015, 15 (7), 3321-3331.
Hazard Statements: H228-H317-H500
Flammable solid. May cause an allergic skin reaction. May form combustible dust concentrations in air
Precautionary Statements: P210-P240-P241-P261-P272-P280-P302+P352-P333+P313-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Avoid breathing dust/fume/gas/mist/vapours/spray. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. If skin irritation or rash 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