aminomethyl propanol
{{Chembox
| ImageFile = 2-amino-2-methyl-1-propanol.svg
| ImageSize = 150px
| ImageAlt =
| PIN = 2-Amino-2-methylpropan-1-ol
| OtherNames = Isobutanol-2-amine
Aminoisobutanol
2-Amino-2-methyl-1-propanol
|Section1={{Chembox Identifiers
| CASNo = 124-68-5
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LU49E6626Q
| PubChem = 11807
| ChemSpiderID = 13835861
| SMILES = CC(C)(CO)N
| StdInChI = 1S/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3
| StdInChIKey = CBTVGIZVANVGBH-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=4 | H=11 | N=1 | O=1
| Appearance =
| Density = 0.934 g/cm3
| MeltingPtC = 30-31
| BoilingPtC = 165.5
| Solubility = Miscible
| SolubleOther = Soluble
| Solvent = alcohols
}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|412}}
| PPhrases = {{P-phrases|264|264+265|273|280|302+352|305+351+338|321|332+317|337+317|362+364|501}}
| MainHazards = Irritant
| FlashPt =
| AutoignitionPt =
| NFPA-F = 2
| NFPA-H = 2
| NFPA-R = 0
}}
}}
Aminomethyl propanol (AMP) is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.
Aminomethyl propanol is typically sold as a solution of the material in water, for which different concentrations are available.
Synthesis
Aminomethyl propanol can be produced by the hydrogenation of 2-aminoisobutyric acid or its esters.
Properties
Aminomethyl propanol is soluble in water{{cite journal|last1=Bougie|first1=Francis|last2=Iliuta|first2=Maria|title=Sterically Hindered Amine-Based Absorbents for the Removal of CO2 from Gas Streams|journal=J Chem Eng Data|date=2012-02-14|volume=57|issue=3|pages=635–669|doi=10.1021/je200731v}} and about the same density as water.
Uses
Aminomethyl propanol is used for the preparation of buffer solutions.{{cite web|title=2-Amino-2-methyl-1-propanol|url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB0320043.htm|website=Chemical Book|access-date=14 August 2014}} It is a component of the drugs ambuphylline and pamabrom. It is also used in cosmetics.{{cite web|title=Aminomethyl-propanol|url=http://cosmeticsinfo.org/ingredient/aminomethyl-propanol|website=Cosmetics Info|access-date=14 August 2014|archive-date=14 August 2014|archive-url=https://web.archive.org/web/20140814124332/http://cosmeticsinfo.org/ingredient/aminomethyl-propanol|url-status=dead}}
It is a precursor to oxazolines via its reaction with acyl chlorides.{{cite journal|title=2,2'-Dimethoxy-6-Formylbiphenyl|author1=Albert I. Meyers |author2=Mark E. Flanagan|journal=Org. Synth.|year=1993|volume=71|page=107|doi=10.15227/orgsyn.071.0107}} Via sulfation of the alcohol, the compound is also a precursor to 2,2-dimethylaziridine.{{cite journal|title=Tert-butylamine|author1=Kenneth N. Campbell |author2=Armiger H. Sommers |author3=Barbara K. Campbell |author4=Lee Irvin Smith |author5=Oliver H. Emerson |author6=D. E. Pearson |author7=J. F. Baxter |author8=K. N. Carter|journal= Org. Synth.|year=1947|volume=27|page=12|doi=10.15227/orgsyn.027.0012}}
Aminomethyl propanol is used as an intermediate the synthesis of fepradinol, isobucaine, and radafaxine.{{cn|date=April 2024}}