Hexamethylenetetramine

• Catalog No.: A17213
• CAS Number: 100-97-0
• M. F.: C6H12N4
• M. W.: 140.18628
• Purity: 99+%

SYNONYMS

• Title: 六亚甲基四胺
• IUPAC name: 1,3,5,7-tetraazatricyclo[3.3.1.1^3,^7]decane
• IUPAC Traditional name: methenamine
• Synonyms: Hexamine; Methenamine

DATABASE IDS

• MDL Number: MFCD00006895
• EC Number: 202-905-8
• CAS Number: 100-97-0
• Merck Index: 145966
• Beilstein Number: 2018

PROPERTIES

• Purity: 99+%
• Density: 1.33
• Flash Point: 250°C(482°F)
• Melting Point: ca 280°C subl.
• GHS Hazard statements: H228-H302-H317
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P261-P302+P352-P321-P501A
• Risk Statements: 11-43
• RTECS: MN4725000
• Safety Statements: 24-37
• Storage Warning: Hygroscopic
• TSCA Listed: 是
• Hazard Class: 4.1
• UN Number: UN1328
• Packing Group: III

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.