Boc-1-amino-3,6-dioxa-8-octanediamine Chemical Properties

Boiling point:

365.2±27.0 °C(Predicted)

Density 

1.046 g/mL at 20 °C

refractive index 

1.4570 to 1.4610

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

clear liquid

pka

12.23±0.46(Predicted)

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C11H24N2O4/c1-11(2,3)17-10(14)13-5-7-16-9-8-15-6-4-12/h4-9,12H2,1-3H3,(H,13,14)

InChIKey

OCUICOFGFQENAS-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCOCCOCCN

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

2735

WGK Germany 

3

F 

10-21

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-1-amino-3,6-dioxa-8-octanediamine Usage And Synthesis

Description

t-Boc-N-Amido-PEG2-amine is a PEG linker containing an amino group and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Chemical Properties

Light yellow oil

Uses

Linker reagent for the prep. of a broad variety of linked tags, monomers for polymerisation, ionophores etc., e.g. biotinylation reagents.

reaction suitability

reagent type: cross-linking reagent

Synthesis

General procedure: A dichloromethane solution (10 mL/mmol) of 1,8-diamino-3,6-dioxaoctane (1 eq.) was treated with di-tert-butyl dicarbonate (0.15 eq.) at 0 °C, kept at 0 °C for 5 hours, and then the reaction was continued at room temperature for 18 hours. Upon completion of the reaction, the organic phase was washed with water until all unreacted 1,8-diamino-3,6-dioxaoctane was removed by extraction. The organic phase was dried over anhydrous magnesium sulfate and recovered quantitatively to give the Boc-protected product tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate, which was concentrated under vacuum. The product characterization data were as follows:11a: 1H NMR (300 MHz, CDCl3): δ 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2).11b: 1H NMR ( 300 MHz, CDCl3): δ 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).

IC 50

PEGs

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4208 - 4212
[2] Tetrahedron, 2012, vol. 68, # 52, p. 10818 - 10826
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 17, p. 2678 - 2685
[4] Journal of the American Chemical Society, 2013, vol. 135, # 34, p. 12684 - 12689
[5] Tetrahedron, 2017, vol. 73, # 33, p. 4972 - 4978

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