Ethanimine

Ethanimine / ethenamine

Names

Preferred IUPAC name

Ethanimine

Other names

As imine: ethylimine, ethylideneimine, ethylidenimine, acetaldehyde imine, acetaldehyde-ammonia Schiff base, acetaldimine, iminoethane
As amine: ethenamine, ethyleneamine, ethylideneamine, aminoethylene, vinylamine, vinyl amine

Identifiers

CAS Number

20729-41-3

3D model (JSmol)

Interactive image

ChemSpider

11539075

PubChem CID

140746

InChI

InChI=1S/C2H5N/c1-2-3/h2-3H,1H3
Key: MPAYEWNVIPXRDP-UHFFFAOYSA-N
InChI=1/C2H5N/c1-2-3/h2-3H,1H3
Key: MPAYEWNVIPXRDP-UHFFFAOYAR

SMILES

CC=N

Properties

Chemical formula

C₂H₅N

Molar mass

43.069 g·mol⁻¹

Related compounds

N-Methylmethanimine
Methanimine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Ethanimine is an organonitrogen compound classified as an imine. It is formed by reacting acetaldehyde and ammonia, but rapidly polymerizes to acetaldehyde ammonia trimer.

It has two tautomers: ethanimine, an imine, and ethenamine or aminoethylene, an amine. Ethanimine has two hydrogens on the carbon, while ethenamine has two on the nitrogen atom.

Occurrence

It is not well known terrestrially, but has been detected in abundance toward Sagittarius B2 (Sgr B2), a dense interstellar cloud between stars toward the Galactic Center of the Milky Way. The distance between the Sgr B2 cloud and center of galaxy is 100 pc (1 pc = 3.26 ly). Ethanimine is mainly found in hot cores of ISM clouds; in case of Sgr B2, the region would be the Sgr B2 N and Sgr B2 M.^[1] Radio telescopes such as the Green Bank Observatory's Green Bank Telescope and those operated by the National Radio Astronomy Observatory (measuring radio frequency light lambda ranging from 1–300 GHz) are able to detect organic molecules such as ethanimines because its internal energy transition, more specifically the rotational transition is within the radio frequency of 14085 MHz = 140.8 GHz.^[2]

References

^ Miao, Yanti; Mehringer, David M.; Kuan, Yi-Jheng; Snyder, Lewis E. (1995). "Complex molecules in Sagittarius B2(N): The importance of grain chemistry". The Astrophysical Journal. 445: L59. Bibcode:1995ApJ...445L..59M. doi:10.1086/187889.
^ Danger, G.; Bossa, J.-B.; De Marcellus, P.; Borget, F.; Duvernay, F.; Theulé, P.; Chiavassa, T.; d'Hendecourt, L. (2011). "Experimental investigation of nitrile formation from VUV photochemistry of interstellar ices analogs: Acetonitrile and amino acetonitrile". Astronomy & Astrophysics. 525: A30. Bibcode:2011A&A...525A..30D. doi:10.1051/0004-6361/201015736.

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N₂H⁺ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water
Four atoms	Acetylene Ammonia Cyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol
Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal
Nine atoms	Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) C₇₀ fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine Heptatrienyl radical