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Hexamethylenetetramine information


Hexamethylenetetramine
Names
Preferred IUPAC name
1,3,5,7-Tetraazaadamantane
Other names
  • Hexamine
  • Methenamine
  • Urotropine
  • Formin
  • Aminoform
  • HMTA
Identifiers
CAS Number
  • 100-97-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
2018
ChEBI
  • CHEBI:6824 checkY
ChEMBL
  • ChEMBL1201270 checkY
ChemSpider
  • 3959 checkY
DrugBank
  • DB06799
ECHA InfoCard 100.002.642 Edit this at Wikidata
EC Number
  • 202-905-8
E number E239 (preservatives)
Gmelin Reference
26964
KEGG
  • D00393 checkY
MeSH Methenamine
PubChem CID
  • 4101
RTECS number
  • MN4725000
UNII
  • J50OIX95QV checkY
UN number 1328
CompTox Dashboard (EPA)
  • DTXSID6020692 Edit this at Wikidata
InChI
  • InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 checkY
    Key: VKYKSIONXSXAKP-UHFFFAOYSA-N checkY
  • InChI=1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
    Key: VKYKSIONXSXAKP-UHFFFAOYAW
SMILES
  • C1N2CN3CN1CN(C2)C3
Properties
Chemical formula
C6H12N4
Molar mass 140.186 g/mol
Appearance White crystalline solid
Odor Fishy, ammonia like
Density 1.33 g/cm3 (at 20 °C)
Melting point 280 °C (536 °F; 553 K) (sublimes)
Solubility in water
85.3 g/100 mL
Solubility Soluble in chloroform, methanol, ethanol, acetone, benzene, xylene, ether
Solubility in chloroform 13.4 g/100 g (20 °C)
Solubility in methanol 7.25 g/100 g (20 °C)
Solubility in ethanol 2.89 g/100 g (20 °C)
Solubility in acetone 0.65 g/100 g (20 °C)
Solubility in benzene 0.23 g/100 g (20 °C)
Acidity (pKa) 4.89[1]
Pharmacology
ATC code
J01XX05 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly combustible, harmful
GHS labelling:
Pictograms
GHS02: Flammable GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H228, H317
Precautionary statements
P210, P240, P241, P261, P272, P280, P302+P352, P321, P333+P313, P363, P370+P378, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point 250 °C (482 °F; 523 K)
Autoignition
temperature
410 °C (770 °F; 683 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hexamethylenetetramine, also known as methenamine, hexamine, or its trade name Urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like structure similar to adamantane. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives. It sublimes in vacuum at 280 °C.

  1. ^ Cooney AP, Crampton MR, Golding P (1986). "The acid-base behaviour of hexamine and its N-acetyl derivatives". J. Chem. Soc., Perkin Trans. 2 (6): 835–839. doi:10.1039/P29860000835.

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Hexamethylenetetramine

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Hexamethylenetetramine, also known as methenamine, hexamine, or its trade name Urotropin, is a heterocyclic organic compound with the formula (CH2)6N4...

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Adamanzane

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Structure of hexamethylenetetramine...

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Formazine

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heterocyclic polymer produced by reaction of hexamethylenetetramine with hydrazine sulfate. The hexamethylenetetramine tetrahedral cage-like structure, similar...

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RDX

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(patent No. 104280) for its manufacture by nitrolysis of hexamine (hexamethylenetetramine) with concentrated nitric acid. In this patent, the medical properties...

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Duff reaction

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who Duff, J. C.; Bills, E. J. (1934). "282. Reactions between hexamethylenetetramine and phenolic compounds. Part II. Formation of phenolic aldehydes...

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Nitramide

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nitramides are important explosives. They are prepared by nitrolysis of hexamethylenetetramine. https://pubchem.ncbi.nlm.nih.gov/compound/Nitramide Häußler, A...

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Structural isomer

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case also for the hydrogen atoms cyclopentane, allene, 2-butyne, hexamethylenetetramine, prismane, cubane, dodecahedrane, etc. On the other hand, the hydrogen...

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Polyamine

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triazinane), and it serves as a water-soluble hydrogen sulfide scavenger. Hexamethylenetetramine (hexamine) is another product of formaldehyde and ammonia that has...

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Aminomethanol

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with formaldehyde and ammonia. It is an intermediate en route to hexamethylenetetramine. The reaction can be conducted in gas phase and in solution. Berski...

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Ammonia

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compounds include alprazolam, ethanolamine, ethyl carbamate and hexamethylenetetramine. Nitric acid is generated via the Ostwald process by oxidation of...

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Ammonia solution

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alkyl amines, although anhydrous ammonia is usually preferred. Hexamethylenetetramine forms readily from aqueous ammonia and formaldehyde. Ethylenediamine...

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Methylene blue

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induces methemoglobinemia, reversing this pathway. Hyoscyamine/­hexamethylenetetramine/­phenyl salicylate/­methylene blue/­benzoic acid (trade names Methylphen...

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Tetramine

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amine groups. Some examples are: Triethylenetetramine ("trien") Hexamethylenetetramine (hexamine) Tetramethylenedisulfotetramine (TETS), a rodenticide...

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HMT

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HMT may refer to: Science Hexamethylenetetramine Histamine N-methyltransferase Histone methyltransferase Host modulatory therapy Places Ham Street railway...

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Methylene imine

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methylene imine from the reaction of ammonia and formaldehyde produces hexamethylenetetramine. Vuitton, V.; Yelle, R. V.; Anicich, V. G. (2006). "The nitrogen...

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Mary Mallon

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to destroy her kidneys. That was changed to brewer's yeast and hexamethylenetetramine in increasing doses. She was first told that she had typhoid in...

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Acetone imine

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Methylene imine (CH2=NH) is also highly reactive, condensing to hexamethylenetetramine. Upon standing, acetone imine undergoes further condensation to...

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Deodorant

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products can have both drying and bactericidal effects. Methenamine (hexamethylenetetramine, also known as hexamine or urotropin) is a powerful antiperspirant...

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Phenol formaldehyde resin

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thermoplastic and require a curing agent or hardener to form a thermoset. Hexamethylenetetramine is a hardener added to crosslink novolac. At a temperature greater...

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Ineos

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propylene oxide Paraform * Cyanates, dimethoxymethane, formaldehyde, hexamethylenetetramine, paraformaldehyde, and triallylcyanurate Phenol Acetone, alpha-methylstyrene...

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Acetaldehyde ammonia trimer

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molecule has C3v point group symmetry. The compound is related to hexamethylenetetramine, which is the condensation product of ammonia and formaldehyde....

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Chemical weapons in World War I

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PH helmet, was issued in January 1916, and was impregnated with hexamethylenetetramine to improve protection against phosgene. Self-contained box respirators...

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Adamantane

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pentoxide P4O10 = (PO)4O6, phosphorus pentasulfide P4S10 = (PS)4S6, and hexamethylenetetramine C6N4H12 = N4(CH2)6. Particularly notorious is tetramethylenedisulfotetramine...

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Hemiaminal

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stable, as they tend to dehydrate to form imines which polymerise to hexamethylenetetramine. A rare stable example is the adduct of ammonia and hexafluoroacetone...

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