5-Amino-1-pentanol
From Wikipedia, the free encyclopedia
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| Names | |
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| Preferred IUPAC name
5-Aminopentan-1-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.017.926 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| 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] | |
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| Danger | |
| H302, H314 | |
| 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).
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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.
The complete hydrogenation of furfural (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]
