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| | 5-(Boc-amino)-1-pentanol Basic information |
| Product Name: | 5-(Boc-amino)-1-pentanol | | Synonyms: | N-T-BUTOXYCARBONYL-5-AMINO-1-PENTANOL;N-(5-HYDROXYPENTYL)CARBAMIC ACID TERT-BUTYL ESTER;1-(tert-Butoxycarbonylamino)-5-pentanol;5-(Boc-amino)pentan-1-ol;5-(N-tert-Butoxycarbonyl)amino-1-pentanol;5-[[(t-Butyloxy)carbonyl]amino]pentanol;N-(tert-Butoxycarbonyl)-5-aminopentanol;N-(5-Hydroxypentyl)carbaMic Acid 1,1-DiMethylethyl Ester | | CAS: | 75178-90-4 | | MF: | C10H21NO3 | | MW: | 203.28 | | EINECS: | | | Product Categories: | All Aliphatics;Aliphatics | | Mol File: | 75178-90-4.mol |  |
| | 5-(Boc-amino)-1-pentanol Chemical Properties |
| Boiling point | 318.4±25.0 °C(Predicted) | | density | 1.00 g/mL at 20 °C(lit.) | | refractive index | n20/D 1.45 | | Fp | >109°C | | storage temp. | 2-8°C | | solubility | Chloroform, Dichloromethane, Ethyl Acetate, Methanol | | form | Oil | | pka | 12.88±0.46(Predicted) | | color | Pale Yellow | | Water Solubility | Difficult to mix in water. | | Sensitive | Moisture Sensitive | | BRN | 3603659 | | InChI | 1S/C10H21NO3/c1-10(2,3)14-9(13)11-7-5-4-6-8-12/h12H,4-8H2,1-3H3,(H,11,13) | | InChIKey | DDGNGFVNTZJMMZ-UHFFFAOYSA-N | | SMILES | CC(C)(C)OC(=O)NCCCCCO | | CAS DataBase Reference | 75178-90-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | Safety Statements | 23-24/25 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Irritant | | HS Code | 2921490090 | | Storage Class | 10 - Combustible liquids |
| | 5-(Boc-amino)-1-pentanol Usage And Synthesis |
| Description | 5-(Boc-amino)-1-pentanol is a linker containing a hydroxyl group and Boc-protected amino group. The hydroxyl group enables further derivatization or replacement with other reactive functional groups. The Boc group can be deprotected under mild acidic conditions to form the free amine. | | Chemical Properties | Pale Yellow Oil | | Uses | 5-(Boc-amino)-1-pentanol may also be used as non-limiting linkers. | | Uses | Linker (anthraquinone-oligopeptide) | | Synthesis Reference(s) | Synthetic Communications, 20, p. 773, 1990 DOI: 10.1080/00397919008052321 | | reaction suitability | reagent type: cross-linking reagent | | Synthesis | The general procedure for the synthesis of 5-(N-tert-butoxycarbonylamino)-1-pentanol from 5-amino-1-pentanol and di-tert-butyl dicarbonate is as follows:
1. 5-amino-1-pentanol (15.0 g, 145.4 mmol) was dissolved in water (140 mL) and saturated aqueous NaHCO3 solution (1.4 mL) in a 1.0 L single-necked round-bottomed flask.
2. To the above solution was slowly added a solution of di-tert-butyl dicarbonate (33.3 g, 152.7 mmol) in THF (280 mL).
3. The reaction mixture was stirred overnight at room temperature, keeping the flask open to the atmosphere.
4. Upon completion of the reaction, the reaction mixture was diluted with saturated aqueous NaHCO3 solution (90 mL) and extracted with EtOAc (400 mL).
5. The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent evaporated to give 28.9 g (98% yield) of 5-(N-tert-butoxycarbonylamino)-1-pentanol as a clear colorless oil.
6. The purity of the product was confirmed by NMR analysis and no further purification was carried out.
Note: 5-(N-Boc-amino)-1-pentanol is also available from TCI America (Portland, OR). | | References | [1] Synthesis, 1990, p. 366 - 368
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
[3] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2833 - 2836
[4] Carbohydrate Research, 1999, vol. 322, # 3-4, p. 201 - 208
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1376 - 1392 |
| | 5-(Boc-amino)-1-pentanol Preparation Products And Raw materials |
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