Aminomethyl propanol explained

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^[1] and about the same density as water.

Uses

Aminomethyl propanol is used for the preparation of buffer solutions.^[2] It is a component of the drugs ambuphylline and pamabrom. It is also used in cosmetics.^[3]

It is a precursor to oxazolines via its reaction with acyl chlorides.^[4] Via sulfation of the alcohol, the compound is also a precursor to 2,2-dimethylaziridine.^[5]

Aminomethyl propanol is used as an intermediate the synthesis of fepradinol, isobucaine, and radafaxine.

Notes and References

1. Bougie. Francis. Iliuta. Maria. Sterically Hindered Amine-Based Absorbents for the Removal of CO2 from Gas Streams. J Chem Eng Data. 2012-02-14. 57. 3. 635–669. 10.1021/je200731v.
2. Web site: 2-Amino-2-methyl-1-propanol. Chemical Book. 14 August 2014.
3. Web site: Aminomethyl-propanol. Cosmetics Info. 14 August 2014. 14 August 2014. https://web.archive.org/web/20140814124332/http://cosmeticsinfo.org/ingredient/aminomethyl-propanol. dead.
4. 2,2'-Dimethoxy-6-Formylbiphenyl. Albert I. Meyers . Mark E. Flanagan. Org. Synth.. 1993. 71. 107. 10.15227/orgsyn.071.0107.
5. Tert-butylamine. Kenneth N. Campbell . Armiger H. Sommers . Barbara K. Campbell . Lee Irvin Smith . Oliver H. Emerson . D. E. Pearson . J. F. Baxter . K. N. Carter. Org. Synth.. 1947. 27. 12. 10.15227/orgsyn.027.0012.