| Identification | Back Directory | [Name]
6-(BOC-AMINO)-HEXYL BROMIDE | [CAS]
142356-33-0 | [Synonyms]
Boc-NH-C6-Br
N-Boc-6-BroMohexylaMin
N-BOC-6-BROMO-HEXYLAMINE
tert-butyl 6-broMohexylcarbaMate
ert-Butyl(6-bromohexyl)carbamate
N-Boc-6-Bromohexylamine≥ 95% (NMR)
6-(Boc-amino)hexyl bromide >=97.0% (GC)
N-(tert-Butoxycarbonyl)-6-broMohexylaMine
(6-Bromo-hexyl)-carbamic acid tert-butyl ester
N-(6-BroMohexyl)carbaMic Acid 1,1-DiMethylethyl Ester
Carbamic acid, N-(6-bromohexyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H22BrNO2 | [MDL Number]
MFCD06201019 | [MOL File]
142356-33-0.mol | [Molecular Weight]
280.2 |
| Chemical Properties | Back Directory | [Boiling point ]
340.1±25.0 °C(Predicted) | [density ]
1.192 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.473
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Sparingly), Ethyl Acetate (Sparingly), Methanol (Slightly) | [form ]
liquid | [pka]
12.91±0.46(Predicted) | [color ]
Colourless to light yellow | [InChI]
InChI=1S/C11H22BrNO2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8-12/h4-9H2,1-3H3,(H,13,14) | [InChIKey]
NXQXVXILNVTMNA-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NCCCCCCBr |
| Hazard Information | Back Directory | [Chemical Properties]
6-(BOC-AMINO)-HEXYL BROMIDE is Colourless Liquid
| [Uses]
6-(BOC-AMINO)-HEXYL BROMIDE is an intermediate used in the synthesis of fluorescent indicators and various inhibitors
| [reaction suitability]
reagent type: cross-linking reagent | [Synthesis]
Synthesis of N-BOC-6-bromohexylamine from 6-(BOC-amino)-1-hexanol General procedure: To 6-(BOC-amino)-1-hexanol (0.500 g, 2.82 mmol, 1 eq.) dissolved in a 1:1 dioxane/water mixture (12 mL) was added K2CO3 (1.870 g, 13.56 mmol, 4 eq.) and stirred for 10 min at room temperature. stirred for 10 minutes at room temperature. Subsequently, di-tert-butyl dicarbonate (0.7 mL, 3.39 mmol, 1.2 eq.) was added to the mixture and stirring was continued overnight. After completion of the reaction, the reaction mixture was diluted with EtOAc (12 mL) and the organic layer was separated. The organic layer was sequentially washed with 10% HCl (2 x 10 mL), dried with MgSO4 and then concentrated in vacuum. The product 0.570 g (2.62 mmol, 93% yield) was obtained, which could be used in the next step without further purification. Thin layer chromatography (TLC) showed an Rf value of 0.50 (silica gel, 60% EtOAc/Hex).1H NMR (400 MHz, CDCl3) δ: 4.51 (br s, 1H), 3.61 (t, J = 6.5 Hz, 2H), 3.09 (t, J = 6.7 Hz, 2H), 1.42 (s, 9H), 1.55-1.30 ( m, 8H) ppm.13C NMR (100 MHz, CDCl3) δ: 156.1, 79.0, 62.7, 40.4, 32.6, 30.1, 28.4, 26.4, 25.3 ppm.The NMR spectra were in agreement with the literature report [41].
Next, CBr4 (0.920 g, 2.76 mmol, 1 eq.) and PPh3 (0.720 g, 2.76 mmol, 1 eq.) were added to 6-(tert-butoxycarbonylamino)hexan-1-ol (0.600 g, 2.76 mmol, 1 eq.) dissolved in anhydrous dichloromethane (14 mL) and the reaction was carried out at 0 °C. The reaction mixture was slowly warmed up to room temperature over 2 hours. Upon completion of the reaction, the mixture was concentrated in vacuum and purified by column chromatography to afford the product 0.696 g (2.48 mmol, 90% yield). Thin layer chromatography (TLC) showed an Rf value of 0.57 (silica gel, 20% EtOAc/Hex).1H NMR (400 MHz, CDCl3) δ: 4.48 (br s, 1H), 3.66 (t, J = 6.8 Hz, 2H), 3.09 (t, J = 6.5 Hz, 2H), 1.88-1.82 (m, 2H), 1.47 ( s, 9H), 1.54-1.18 (m, 6H) ppm. 13C NMR (100 MHz, CDCl3) δ: 156.1, 62.9, 51.1, 32.8, 28.5, 26.4, 25.4 ppm. the NMR spectra were in agreement with the literature reports [42]. | [IC 50]
Non-cleavable Linker | [References]
[1] Helvetica Chimica Acta, 1993, vol. 76, # 2, p. 884 - 892
[2] Biochimica et Biophysica Acta - General Subjects, 2016, vol. 1860, # 3, p. 486 - 497
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 510 - 515
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4033 - 4036
[5] Patent: WO2015/77503, 2015, A1. Location in patent: Paragraph 00400 |
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