Hexamethylenetetramine, 99+%

CAS Number 100-97-0 Synonyms
  • Hexamine
  • Methenamine

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Hexamethylenetetramine, 99+%

MDL: MFCD00006895
EINECS: 202-905-8

Chemical Properties

Formula: C6H12N4  Flash point: 250°(482°F)
Formula weight: 140.19  Density: 1.33
Melting point: ca 280° subl. Sensitivity: Hygroscopic

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements : H228-H317

Flammable solid. May cause an allergic skin reaction.

Precautionary Statements : P210-P261-P280-P240-P363-P501A

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Wash contaminated clothing before reuse. Dispose of contents/container in accordance with local/regional/national/international regulations.

FlammableHarmful or Irritant

Other References

Merck: 14,5966
Beilstein: 2018
UN#: UN1328
Hazard Class: 4.1
Packing Group: III
Harmonized Tariff Code: 2933.69
RTECS: MN4725000
Hexamethylenetetramine, 99+% - CAS 100-97-0 - Formula C6H12N4


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