| Identification | More | [Name]
N-tert-Butoxycarbonyl-1,6-hexanediamine | [CAS]
51857-17-1 | [Synonyms]
1-BOC-1,6-DIAMINOHEXANE
1-BOC-AMINO-1,6-HEXANEDIAMINE
AURORA KA-4392
AURORA KA-7545
AURORA KA-7567
N-(6-AMINOHEXYL)CARBAMIC ACID TERT-BUTYL ESTER
N-BOC-1,6-DIAMINOHEXANE
N-BOC-1,6-HEXANEDIAMINE
N-(TERT-BUTOXYCARBONYL)-1,6-DIAMINOHEXANE
N-(TERT-BUTOXYCARBONYL)-1,6-HEXANEDIAMINE
TERT-BUTYL N-(6-AMINOHEXYL)CARBAMATE
TIMTEC-BB SBB006530
N-t-BOC-1,6-HEXANEDIAMINE
(6-Aminohexyl)carbamic Acid tert-Butyl Ester
1-((tert-Butoxycarbonyl)amino)-6-aminohexane
N-(6-Aminohexyl)-carbamic Acid 1,1-Dimethylethyl Ester
n-(tert-butoxycarbonyl)hexamethylenediamine
N-tert-Butoxycarbonyl-1,6-hexanediamine
N-Boc-1,6-diaminohexane
N-(6-Aminohexyl)carbamic acid tert-butyl ester
tert-butyl 6-aminohexylcarbamate
N-Boc-1,6-diaminohexane, tert-Butyl-N-(6-aminohexyl)carbamate
(6-Aminohexyl)carbamic acid 1,1-dimethylethyl ester | [EINECS(EC#)]
628-984-2 | [Molecular Formula]
C11H24N2O2 | [MDL Number]
MFCD00671489 | [Molecular Weight]
216.32 | [MOL File]
51857-17-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Boiling point ]
106-110 °C (0.3 mmHg) | [density ]
0.965 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.462
| [Fp ]
125 °C
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Soluble in dichloromethane and ethyl acetate. | [form ]
Viscous Liquid | [pka]
12.93±0.46(Predicted) | [color ]
Clear light yellow | [Sensitive ]
Air Sensitive | [BRN ]
2089264 | [InChI]
InChI=1S/C11H24N2O2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8-12/h4-9,12H2,1-3H3,(H,13,14) | [InChIKey]
RVZPDKXEHIRFPM-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NCCCCCCN | [CAS DataBase Reference]
51857-17-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2735 8/PG 2
| [WGK Germany ]
3
| [F ]
10-34 | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29241900 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Application]
N-Boc-1,6-hexanediamine can be used as a linear hexyl spacer (C6-spacer) to synthesize:
Biodegradable poly(disulfide amine)s for gene delivery.
A multifunctional dendrimer for theranostics.
Polyamide platinum anti-cancer complexes designed to target cancer specific DNA sequences.
Self-assembled monolayers (SAMs) that resist adsorption of proteins.
[N-(6-(4-Hydroxy-6-isopropylamino-1,3,5-triazin-2-ylamino)hexyl)-5-hydroxy-1,4-naphthoquinone-3-propionamide] (JUG-HATZ), which can be used in designing electrochemical immunosensors. | [Uses]
N-Boc-1,6-hexanediamine can be used as a linear hexyl spacer (C6-spacer) to synthesize:
- Biodegradable poly(disulfide amine)s for gene delivery.
- A multifunctional dendrimer for theranostics.
- Polyamide platinum anti-cancer complexes designed to target cancer specific DNA sequences.
- Self-assembled monolayers (SAMs) that resist adsorption of proteins.
- [N-(6-(4-Hydroxy-6-isopropylamino-1,3,5-triazin-2-ylamino)hexyl)-5-hydroxy-1,4-naphthoquinone-3-propionamide] (JUG-HATZ), which can be used in designing electrochemical immunosensors.
| [Uses]
N-Boc-1,6-diaminohexane is used to prepare 1,3-Bis[6-(Boc-amino)hexyl]urea by reacting with carbonyl dichloride in the presence of triethylamine. Further, it is used as a reagent for the introduction of a C6-spacer. | [Preparation]
synthesis of N-BOC-1,6-diaminohexane: 1,6-Diaminohexane 3 (Fig. 1) (100 g, 0.86 mol) was dissolved in CH2Cl2 (300 ml) and cooled in an ice bath to 0–3°C. To the stirred solution 0.3 eq. di-tert-butyl bicarbonate (62.6 g, 0.29 mol) was added slowly over a period of 1 h. The reaction was allowed to warm up to r.t., and proceeded overnight. The reaction mixture was extracted with saturated aqueous NaHCO3 (50 ml, three times). The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCl and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaO3, and extracted with ethyl acetate. The organic phases were pooled, dried, and evaporated under reduced pressure. The resulting oil was dissolved in 200 ml, 1 N HCL and extracted with ether. The aqueous phase was washed with ether, made basic to a pH of 10 with aqueous 2 N NaOH, and extracted with ethyl acetate. The organic extracts were pooled, dried over Na2SO4 and evaporated to give 10.5 g of homogeneous N-BOC-1, 6- diaminohexane 2c (Fig. 1) as a yellow oil which was used without further purification.
TLC Rf 0.51; 1H NMR (CDCL3) d 4.54 (bs, 1H; NH), 3.05 1 2.62 (m, 4H; NCH2), 1.41 (m, 9H; CH3), 1.29 (m, 8H; CH2).
Evaluation of aminoalkylmethacrylate nanoparticles as colloidal drug carrier systems. Part I: synthesis of monomers, dependence of the physical properties on the polymerization methods | [reaction suitability]
reagent type: cross-linking reagent | [Synthesis]
GENERAL STEPS: 1,6-Diaminohexane (20.0 g, 172 mmol) was suspended in 50 mL of dichloromethane (DCM) at 0 °C. To this suspension was slowly added a solution of di-tert-butyl dicarbonate (Boc2O, 3.75 g, 17.2 mmol) dissolved in 24 mL of DCM. After addition, the ice bath was removed and the reaction mixture was allowed to warm up to room temperature with continuous stirring for 18 hours. After completion of the reaction, the precipitate was removed by filtration and the filtrate was washed sequentially with saturated aqueous sodium bicarbonate (3 x 50 mL), water (2 x 50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give an oily product tert-butyl N-(6-aminohexyl)carbamate 3.1 g in 84% yield. The product was characterized by 1HNMR (300 MHz, CDCl3): δ 4.56 (s, 1H), 3.09 (dd, J=12.6,6.3Hz, 2H), 2.83-2.58 (t, 2H), 1.66-1.17 (m, 17H). | [References]
[1] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2527 - 2532
[2] Journal of Materials Chemistry B, 2014, vol. 2, # 5, p. 502 - 510
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 6956 - 6959
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 5, p. 139 - 145
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6570 - 6580 |
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