Aminomethyl propanol

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Aminomethyl propanol
File:2-amino-2-methyl-1-propanol.svg
Names
Preferred IUPAC name
2-Amino-2-methylpropan-1-ol
Other names
Isobutanol-2-amine
Aminoisobutanol
2-Amino-2-methyl-1-propanol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3
    Key: CBTVGIZVANVGBH-UHFFFAOYSA-N
  • CC(C)(CO)N
Properties
C4H11NO
Molar mass 89.138 g·mol−1
Density 0.934 g/cm3
Melting point 30–31 °C (86–88 °F; 303–304 K)
Boiling point 165.5 °C (329.9 °F; 438.6 K)
Miscible
Solubility in alcohols Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H412
P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P501
NFPA 704 (fire diamond)

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2
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[2] 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[3][4] and about the same density as water.[3]

Uses

Aminomethyl propanol is used for the preparation of buffer solutions.[3] It is a component of the drugs ambuphylline and pamabrom. It is also used in cosmetics.[2] It is a precursor to oxazolines via its reaction with acyl chlorides.[5] Via sulfation of the alcohol, the compound is also a precursor to 2,2-dimethylaziridine.[6] Aminomethyl propanol is used as an intermediate the synthesis of fepradinol, isobucaine, and radafaxine.[citation needed]

References

  1. "2-Amino-2-methyl-1-propanol". pubchem.ncbi.nlm.nih.gov.
  2. 2.0 2.1 "Aminomethyl-propanol". Cosmetics Info. Archived from the original on 14 August 2014. Retrieved 14 August 2014.
  3. 3.0 3.1 3.2 "2-Amino-2-methyl-1-propanol". Chemical Book. Retrieved 14 August 2014.
  4. Bougie, Francis; Iliuta, Maria (2012-02-14). "Sterically Hindered Amine-Based Absorbents for the Removal of CO2 from Gas Streams". J Chem Eng Data. 57 (3): 635–669. doi:10.1021/je200731v.
  5. Albert I. Meyers; Mark E. Flanagan (1993). "2,2'-Dimethoxy-6-Formylbiphenyl". Org. Synth. 71: 107. doi:10.15227/orgsyn.071.0107.
  6. Kenneth N. Campbell; Armiger H. Sommers; Barbara K. Campbell; Lee Irvin Smith; Oliver H. Emerson; D. E. Pearson; J. F. Baxter; K. N. Carter (1947). "Tert-butylamine". Org. Synth. 27: 12. doi:10.15227/orgsyn.027.0012.