Aminomethanol
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424678894
| ImageFile = Methanolamine.svg
| ImageSize = 150px
| ImageName = Methanolamine structural formula
| PIN = Aminomethanol
| OtherNames = Methanolamine
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 3088-27-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = T8C993J0UB
| PubChem = 6420096
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4925662
| SMILES = OCN
| InChI = 1/CH5NO/c2-1-3/h3H,1-2H2
| InChIKey = XMYQHJDBLRZMLW-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/CH5NO/c2-1-3/h3H,1-2H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XMYQHJDBLRZMLW-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=1 | H=5 | N=1 | O=1
| Appearance = Colorless liquid
| Density =
| MeltingPt =
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|Section3={{Chembox Hazards
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Aminomethanol or methanolamine is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal.{{Cite journal|last1=Berski|first1=Sławomir|last2=Gordon|first2=Agnieszka J.|last3=Ćmikiewicz|first3=Agnieszka|date=2018-02-01|title=Characterisation of the reaction mechanism between ammonia and formaldehyde from the topological analysis of ELF and catastrophe theory perspective|journal=Structural Chemistry|language=en|volume=29|issue=1|pages=243–255|doi=10.1007/s11224-017-1024-x|bibcode=2018StrCh..29..243C |s2cid=103059739|issn=1572-9001|doi-access=free}}
In aqueous solution, methanolamine exists in equilibrium with formaldehyde and ammonia.{{Cite journal|last1=T Feldmann|first1=Michael|last2=Widicus Weaver|first2=Susanna|last3=Blake|first3=Geoffrey|last4=R Kent|first4=David|last5=Goddard|first5=William|date=2005-08-01|title=Aminomethanol water elimination: Theoretical examination|url=https://www.researchgate.net/publication/7678861|journal=The Journal of Chemical Physics|volume=123|issue=3|pages=34304|doi=10.1063/1.1935510|pmid=16080734|bibcode=2005JChPh.123c4304F}} It is an intermediate en route to hexamethylenetetramine.{{cite encyclopedia | chapter=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.}} The reaction can be conducted in gas phase and in solution.
