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
CAS Number	124-68-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	13835861;
ECHA InfoCard	100.004.282
PubChem CID	11807;
UNII	LU49E6626Q ;
CompTox Dashboard (EPA)	DTXSID8027032 ;
	InChI InChI=1S/C4H11NO/c1-4(2,5)3-6/h6H,3,5H2,1-2H3 Key: CBTVGIZVANVGBH-UHFFFAOYSA-N;
	SMILES CC(C)(CO)N;
Properties
Chemical formula	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)
Solubility in water	Miscible
Solubility in alcohols	Soluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H412
Precautionary statements	P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P501
NFPA 704 (fire diamond)	2 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

^ "2-Amino-2-methyl-1-propanol". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b "Aminomethyl-propanol". Cosmetics Info. Archived from the original on 14 August 2014. Retrieved 14 August 2014.
^ ^a ^b ^c "2-Amino-2-methyl-1-propanol". Chemical Book. Retrieved 14 August 2014.
^ 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.
^ Albert I. Meyers; Mark E. Flanagan (1993). "2,2'-Dimethoxy-6-Formylbiphenyl". Org. Synth. 71: 107. doi:10.15227/orgsyn.071.0107.
^ 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.

[1] "2-Amino-2-methyl-1-propanol". pubchem.ncbi.nlm.nih.gov.

[cosm-2] "Aminomethyl-propanol". Cosmetics Info. Archived from the original on 14 August 2014. Retrieved 14 August 2014.

[ChemBk-3] "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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