6-(BOC-AMINO)-HEXYL BROMIDE Chemical Properties

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)

pka

12.91±0.46(Predicted)

form 

liquid

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

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

41-52/53

Safety Statements 

26-39-61

RIDADR 

UN 3082 9/PG 3

WGK Germany 

3

F 

10-21

HS Code 

2924190090

6-(BOC-AMINO)-HEXYL BROMIDE Usage And Synthesis

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

6-(BOC-AMINO)-HEXYL BROMIDE(142356-33-0)Related Product Information

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• TERT-BUTYL 3-(2-BROMOETHYL)PIPERIDINE-1-CARBOXYLATE
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