N-BOC-1,6-diaminohexane

N-BOC-1,6-diaminohexane
  • CAS No.:51857-17-1
Other grades of this product :
N-BOC-1,6-diaminohexane Basic information
Product Name:N-BOC-1,6-diaminohexane
Synonyms:AURORA KA-4392;AURORA KA-7545;AURORA KA-7567;TIMTEC-BB SBB006530;TERT-BUTYL N-(6-AMINOHEXYL)CARBAMATE;N-(6-AMINOHEXYL)CARBAMIC ACID TERT-BUTYL ESTER;N-BOC-1,6-DIAMINOHEXANE;N-BOC-1,6-HEXANEDIAMINE
CAS:51857-17-1
MF:C11H24N2O2
MW:216.32
EINECS:628-984-2
Product Categories:All Aliphatics;Monoprotected Diaminoalkanes;N-Boc-diaminoalkanes;Aliphatics;Amines
Mol File:51857-17-1.mol
N-BOC-1,6-diaminohexane Chemical Properties
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.
pka12.93±0.46(Predicted)
form Viscous Liquid
color Clear light yellow
Sensitive Air Sensitive
BRN 2089264
InChIKeyRVZPDKXEHIRFPM-UHFFFAOYSA-N
CAS DataBase Reference51857-17-1(CAS DataBase Reference)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45
RIDADR UN 2735 8/PG 2
WGK Germany 3
10-34
HazardClass 8
PackingGroup III
HS Code 29241900
MSDS Information
ProviderLanguage
ACROS English
ALFA English
N-BOC-1,6-diaminohexane Usage And Synthesis
Chemical PropertiesOff-White Solid
UsesN-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.
ApplicationN-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.
Preparationsynthesis 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

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