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Paraformaldehyde is used as a fumigant, a disinfectant and in the manufacture of synthetic resins like melamine resin, phenol resin and polyacetal resin. It is also used in cell culture. It also serves as a fixative in electron microscopy. It is also used in the preparation of formalin fixatives for tissues or cells.
Formaldehyde monomer, generated by thermolysis, has been used for the ɑ-hydroxymethylation of dilithiated carboxylic acids. Dehydration of the products affords ɑ-alkyl acrylic acids: J. Org. Chem., 37, 1256 (1972). Monomeric formaldehyde can also be prepared as a THF solution by dehydration with p-Toluenesulfonic anhydride, L00160, and co-distillation of the monomer with the solvent: Synlett, 704 (1990). The use of anhydrous molecular formaldehyde for hydroxymethylation reactions has been discussed: Synlett, 227 (1990).
For use in preparation of Mannich bases, see: Org. Synth. Coll., 3, 305 (1955); 4, 281 (1963). For reviews, see: Org. React., 1, 303 (1942); Synthesis, 703 (1973); Tetrahedron, 46, 1791 (1990).
In the presence of HCl, aromatics undergo chloromethylation. For reviews, see: Org. React., 1, 63 (1942); Russ. Chem. Rev., 46, 891 (1977). Caution! carcinogenic bis(chloromethyl) ether is formed in these reactions. In combination with Hydrobromic acid, A14475, the bromomethylation of aromatics has been effected: J. Org. Chem., 58, 1262 (1993). The same combination also N-bromomethylates phthalimide and other imides: Synlett, 933 (1994).
Reaction with dialkyl phosphites gives hydroxymethyl phosphonates, which, after O-protection, undergo the Horner-Wadsworth-Emmons reaction to give enol ethers. See, e.g.: Org. Synth. Coll., 7, 160 (1990).
Suenobu, T.; Isaka, Y.; Shibata, S.; Fukuzumi, S. Catalytic hydrogen production from paraformaldehyde and water using an organoiridium complex. Chem. Commun. 2015, 51 (9), 1670-1672.
Fuentes, J. A.; Pittaway, R.; Clarke, M. L. Rapid Asymmetric Transfer Hydroformylation (ATHF) of Disubstituted Alkenes Using Paraformaldehyde as a Syngas Surrogate. Chem. Eur. J. 2015, 21 (30), 10645-10649.
Gefahrenhinweise (EU): H228-H302-H332-H314-H318-H317-H351
Flammable solid. Harmful if swallowed. Harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. May cause an allergic skin reaction. Suspected of causing cancer.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.