Hexamethylenetetramine

"Hexamine" redirects here. Not to be confused with Hexylamine.
Hexamethylenetetramine
Names
Preferred IUPAC name
1,3,5,7-Tetraazaadamantane
Other names
  • Hexamine
  • Methenamine
  • Urotropine
  • Formin
  • Aminoform
  • HMTA
Identifiers
3D model (JSmol)
2018
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.642 Edit this at Wikidata
EC Number
  • 202-905-8
E number E239 (preservatives)
26964
KEGG
MeSH Methenamine
RTECS number
  • MN4725000
UNII
UN number 1328
  • 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
  • C1N2CN3CN1CN(C2)C3
Properties
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)
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
J01XX05 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly combustible, harmful
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Warning
H228, H317
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)
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).
checkY verify (what is checkY☒N ?)

Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications.[2][3] It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly water soluble in water and polar organic solvents. It has a cage-like structure similar to adamantane.[3] It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives.[2][3] The compound is also used medically for certain conditions.[4][5] It sublimes in vacuum at 280 °C. The molecule has a tetrahedral cage-like structure, similar to that of adamantane. Four vertices are occupied by nitrogen atoms, which are linked by methylene groups. Although the molecular shape defines a cage, no void space is available at the interior.

  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.
  2. ^ a b Dreyfors JM, Jones SB, Sayed Y (November 1989). "Hexamethylenetetramine: a review". American Industrial Hygiene Association Journal. 50 (11): 579–585. doi:10.1080/15298668991375191. PMID 2688388.
  3. ^ a b c Blažzević, Nikola; Kolbah, D.; Belin, Branka; Šunjić, Vitomir; Kajfež, Franjo (1979). "Hexamethylenetetramine, A Versatile Reagent in Organic Synthesis". Synthesis. 1979 (3). Georg Thieme Verlag KG: 161–176. doi:10.1055/s-1979-28602. ISSN 0039-7881.
  4. ^ Cite error: The named reference LoHammerZegarra2014 was invoked but never defined (see the help page).
  5. ^ Connolly M, de Berker D (2003). "Management of primary hyperhidrosis: a summary of the different treatment modalities". Am J Clin Dermatol. 4 (10): 681–697. doi:10.2165/00128071-200304100-00003. PMID 14507230.