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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.
Hazard Statements: H228-H302-H315-H317-H318-H332-H335-H351-H500
Flammable solid. Harmful if swallowed. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage. Harmful if inhaled. May cause respiratory irritation. Suspected of causing cancer. May form combustible dust concentrations in air
Precautionary Statements: P201-P202-P210-P240-P241-P261-P264b-P270-P271-P272-P280g-P281-P301+P312-P302+P352-P304+P340-P305+P351+P338-P308+P313-P310-P330-P333+P313-P362-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. 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. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. Use personal protective equipment as required. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. 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. IF exposed or concerned: Get medical advice/attention. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant