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Acetaldehyde ammonia trimer

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Acetaldehyde ammonia trimer
Names
Preferred IUPAC name 2,4,6-Trimethyl-1,3,5-triazinane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.201.766 Edit this at Wikidata
EC Number
  • 211-321-2
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H15N3/c1-4-7-5(2)9-6(3)8-4/h4-9H,1-3H3Key: MZSSRMMSFLVKPK-UHFFFAOYSA-N
  • InChI=1/C6H15N3/c1-4-7-5(2)9-6(3)8-4/h4-9H,1-3H3Key: MZSSRMMSFLVKPK-UHFFFAOYAJ
SMILES
  • N1C(NC(NC1C)C)C
Properties
Chemical formula C6H15N3
Molar mass 129.207 g·mol
Appearance Colorless crystals
Melting point 95 to 97 °C (203 to 207 °F; 368 to 370 K)
Solubility polar organic solvents
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Hazard statements H315, H319, H335
Precautionary statements P261, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Acetaldehyde ammonia trimer is a chemical compound described by the formula (CH3CHNH)3. The pure material is colourless but samples often appear light yellow or slightly beige due to the degradation by oxidation. It is hygroscopic, and can be found in a trihydrate form.

As implied by its name, it is a trimeric species formed from the reaction of acetaldehyde and ammonia:

3 CH3CHO + 3 NH3 → (CH3CHNH)3 + 3 H2O

Studies using NMR spectroscopy indicate that the three methyl groups are equatorial, thus the molecule has C3v point group symmetry.

The compound is related to hexamethylenetetramine, which is the condensation product of ammonia and formaldehyde.

References

  1. GHS: PubChem 69486
  2. Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. (1973). "Structure and Chemistry of the Aldehyde Ammonias. 1-Amino-1-alkanols, 2,4,6-Trialkyl-1,3,5-hexahydrotriazines, and N,N-Dialkylidene-1,1-Diaminoalkanes". Journal of Organic Chemistry. 38 (19): 3288–3295. doi:10.1021/jo00959a010.

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