methylene imine
{{Chembox
| ImageFileL1 = Methanimine-2D.png
| ImageSizeL1 =
| ImageAltL1 =
| ImageFileR1 = Methanimine-3D-balls.png
| PIN = Methanimine
| OtherNames = {{ubl|Formaldimine|Azomethine|Formaldehyde imine}}
|Section1={{Chembox Identifiers
| CASNo = 2053-29-4
| PubChem = 123139
| ChEBI = 38220
| ChemSpiderID = 109754
| Gmelin = 163896
| Beilstein = 1900196
| StdInChI=1S/CH3N/c1-2/h2H,1H2
| StdInChIKey = WDWDWGRYHDPSDS-UHFFFAOYSA-N
| SMILES = C=N
}}
|Section2={{Chembox Properties
| Formula = {{chem2|H2C\dNH}}
| C=1|H=3|N=1
| Appearance = colorless gas
| Density =
| MeltingPt =
| MeltingPt_notes =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
|Section8={{Chembox Related
| OtherCompounds = {{ubl|N-Methylmethanimine|Ethanimine|Formaldoxime|Formaldehyde|Ethylene|Imine}}
}}
}}
Methylene imine is an organic compound with the chemical formula {{chem2|H2C\dNH}}. The simplest imine, it is a stable, colorless gas that has been detected throughout the universe.{{cite journal|title=The nitrogen chemistry of Titan's upper atmosphere revealed|last1=Vuitton |first1= V. |last2=Yelle |first2= R. V. |last3= Anicich |first3=V. G.|journal=Astrophysical Journal|year=2006|volume=647|pages=L175-L178|doi=10.1086/507467|doi-access=free}} Structural parameters determined by microwave spectroscopy include a C=N bond length of 1.27 Å, an N–H bond length of 1.02 Å and an {{chem2|H\sN\dC}} bond angle of 110.5°.{{cite journal | author = Richard Pearson Jr., Frank J. Lovas | title = Microwave spectrum and molecular structure of methylenimine (CH2NH) | journal = J. Chem. Phys. | year = 1977 | volume = 66 | page = 4149 | doi = 10.1063/1.434490}} Because unhindered imines polymerize or oligomerize when concentrated, methylene imine has not been isolated as a liquid or bulk solid. Attempted synthesis of methylene imine from the reaction of ammonia and formaldehyde produces hexamethylenetetramine.{{cite encyclopedia | title=Amines, Aliphatic | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | publisher=Wiley-VCH Verlag GmbH | year=2000 | isbn=9783527306732 | doi=10.1002/14356007.a02_001 | last1=Eller | last2=Henkes | last3=Rossbacher | last4=Höke | first1=K. | first2=E. | first3=R. | first4=H.}}
