Substance
ID:718684
Names and Identifiers
Synonyms
MethenamineHexamineHexamethylenetetramine六亚甲基四胺
IUPAC Traditional name
methenamine
IUPAC name
1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
Registration numbers
Beilstein Number
EC Number
MDL Number
CAS Number
Merck Index
Properties
Safety Information
GHS Precautionary statements
P210-P241-P261-P302+P352-P321-P501A
RTECS
MN4725000
European Hazard Symbols
Flammable (F)
Irritant (Xi)Storage Warning
Hygroscopic
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
TSCA Listed
是
Hazard Class
4.1
UN Number
UN1328
GHS Hazard statements
H228-H302-H317
Risk Statements
11-43
Safety Statements
24-37
Packing Group
III
Physical Property
Density
1.33
Flash Point
250°C(482°F)
Melting Point
ca 280°C subl.
Product Information
Purity
99+%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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).
• For a review of applications in organic synthesis, see: Synthesis, 161 (1979).
• 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.