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Aminomethyl propanol

Aminomethyl propanol
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
ECHA InfoCard 100.004.282 Edit this at Wikidata
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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. ^ a b "Aminomethyl-propanol". Cosmetics Info. Archived from the original on 14 August 2014. Retrieved 14 August 2014.
  3. ^ a b c "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.
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