Hexamethylenetetramine

A tertiary amine, C6H12N4, 140.19 g/mol. Boiling point Sublimes, melting point 536 °F (sublimes), as published.

verified recordOrganic — tertiary amine8 measured properties

Identifiers

Molecular formula: C₆H₁₂N₄
Molecular weight: 140.19 g/mol
Exact mass: 140.106196 g/mol
IUPAC name: 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
SMILES: C1N2CN3CN1CN(C2)C3
InChI: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
InChIKey: VKYKSIONXSXAKP-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: Sublimes (NTP, 1992)measured · CAMEO Chemicals
Melting Point: 536 °F (sublimes) (NTP, 1992)measured · CAMEO Chemicals; Sublimes at about 260 °C without melting and with partial decompositionmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.35 at 68 °F (USCG, 1999) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.3394 g/cu cm at 22 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)measured · CAMEO Chemicals; In water, 302,300 mg/L at 25 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.004 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases; 6.1X10-4 mm Hg at 25 °Cmeasured · Hazardous Substances Data Bank (HSDB)
LogP: log Kow = -2.18 at pH 7-9, 20 °Cmeasured · Hazardous Substances Data Bank (HSDB); -2.84measured · ILO-WHO International Chemical Safety Cards (ICSCs)
Flash Point: 482 °F (NTP, 1992)measured · CAMEO Chemicals; 482 °Fmeasured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Refractive Index: Index of refraction: 1.590 /monoclinic, isometric/measured · Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 312; Index of refraction: 1.5911 at 25 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1108

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 140.19 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 140.1061964 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.3calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 13 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 84calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 4calculated · reference compound database
logP: -1.0198calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 12.96 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 4calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 36.558 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 1calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4268calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon6 atoms · 51.4% by mass
N Nitrogen4 atoms · 40.0% by mass
H Hydrogen12 atoms · 8.6% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 10
Total atoms, hydrogen included: 22
Rings: 4
Aromatic rings: 0
Stereocentres: 4
Formal charge: 0

Functional groups

Tertiary amine
Nitrogen bonded to three carbons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Hexamethylenetetramine yet.

Other names for it

The systematic name on this record is 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane.

The sources also call it methenamine, Hexamine, Urotropine, Urotropin, 1,3,5,7-Tetraazaadamantane, Uritone, HMTA, Hexamethylenamine, Formamine, Hexamethylene tetramine, Methenamin.

Structurally related

Nothing structurally close to Hexamethylenetetramine has a page here yet.

Where these values came from

reference compound database4101
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.