Contents

5-Amino-1-pentanol

5-Amino-1-pentanol

Identifiers
CAS Number	2508-29-4 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL333552
ChemSpider	68156
ECHA InfoCard	100.017.926
EC Number	219-718-2
PubChem CID	75634
CompTox Dashboard (EPA)	DTXSID10179771
InChI InChI=1S/C5H13NO/c6-4-2-1-3-5-7/h7H,1-6H2 Key: LQGKDMHENBFVRC-UHFFFAOYSA-N
SMILES C(CCN)CCO
Properties
Chemical formula	C5H13NO
Molar mass	103.16 g·mol−1
Density	0.9488 at 17 °C
Melting point	38.5 °C (101.3 °F; 311.6 K)
Boiling point	221.5 °C (430.7 °F; 494.6 K)
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

5-Amino-1-pentanol is an amino alcohol with a primary amino group and a primary hydroxy group at the ends of a linear C₅-alkanes. As a derivative of the platform chemical furfural (that is easily accessible from pentoses), 5-amino-1-pentanol may become increasingly important in the future as a building block for biodegradable polyesteramides and as a starting material for valerolactam — the monomer for polyamides.

Occurrence and preparation[edit]

The complete hydrogenationoffurfural (furan-2-aldehyde) yields tetrahydrofurfuryl alcohol (2-hydroxymethyltetrahydrofuran), which undergoes ring expansion upon dehydration to give dihydropyran. Dihydropyran reacts with ammonia in a reductive amination under ring opening to produce 5-amino-1-pentanol.^[2]

Product yields of up to 85% can be achieved with a continuous process using a nickel-hydrotalcite catalyst.

Similarly, the hemiacetal 2-hydroxytetrahydropyran^[3] that is formed from dihydropyran with hydrochloric acid can be converted to 5-amino-1-pentanol by reductive amidation with ammonia and hydrogen upon water elimination.^[4]

Properties[edit]

5-Amino-1-pentanol forms white crystalline clumps at solidification temperatures around 35 °C, which dissolve in water, ethanol, and acetone.^[5] The aqueous solution (500 g-l⁻¹) reacts strongly alkaline (pH 13.2 at 20 °C).^[6]

Reactions[edit]

Amino alcohols such as 5-amino-1-pentanol have been studied for their suitability of absorptionofcarbon dioxide.^[7][8]

5-Amino-1-pentanol dehydrates when heated over ytterbium(III) oxide (Yb₂O₃) to give 4-penten-1-amine (I). Also formed piperidine (II), 2,3,4,5-tetrahydropyridine (III), and 1-pentylamine (IV).^[9]

Being bifunctional, 5-amino-1-pentanol reacts in a polycondensation reaction with esters of dicarboxylic acids (or their cyclic acid anhydrides, such as succinic anhydride) to give polyesteramides. These polymers have been investigated as biodegradable plastics, e.g. absorbable sutures.^[10][11] During the reaction, the succinic anhydride reacts initially with the nucleophilic amino group to form an ω-hydroxycarboxylic acid, which is subsequently polycondensed with carbodiimides, such as the hydrochlorideof1-ethyl-3-(3-dimethylaminopropyl)carbodiimides (EDC-HCl).

In a dehydrogenation, catalyzed by rhodium and ruthenium complexes, valerolactam, the δ-lactam of 5-aminopentanoic acid, is formed from 5-amino-1-pentanol in high (94%) yield.^[12][13]

Valerolactam could be of relevance for polyamide 5. Polyamide 5 has garnered little attention so far but is of interest due to its ferroelectricity.^[14]

References[edit]