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83060

Sigma-Aldrich

tert-Butyl 12-amino-4,7,10-trioxadodecanoate

technical, ≥80% (T)

Synonym(s):

Amino-PEG3-tert-butyl ester, tert-Butyl 3-[2-(2-(2-aminoethoxy)ethoxy)ethoxy]propionate

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About This Item

Empirical Formula (Hill Notation):
C13H27NO5
CAS Number:
252881-74-6
Molecular Weight:
277.36
MDL number:
MFCD06201017
UNSPSC Code:
12352200
PubChem Substance ID:
57652942
NACRES:
NA.22

grade

technical

Quality Level

100

Assay

≥80% (T)

form

solid

reaction suitability

reagent type: cross-linking reagent

storage temp.

−20°C

SMILES string

CC(C)(C)OC(=O)CCOCCOCCOCCN

InChI

1S/C13H27NO5/c1-13(2,3)19-12(15)4-6-16-8-10-18-11-9-17-7-5-14/h4-11,14H2,1-3H3

InChI key

CWFSAZJIJBTKRC-UHFFFAOYSA-N

Application

tert-Butyl 12-amino-4,7,10-trioxadodecanoate is generally used as a spacer or linker in bioconjugate chemistry. Some of its applications are:
  • Synthesis of the tetanus-toxin conjugate of MUC1 glycopeptide antigen, as a potential antitumor vaccine.
  • Synthesis of self-assembled monolayer-based surface-enhanced raman scattering (SERS) labels for immuno-SERS microscopy.
  • Synthesis of polycationic adamantane-based dendrons for cell imaging.
  • Synthesis of phthalocyanine (Pc)-peptide conjugates as potential fluorescence imaging agents for cancers overexpressing epidermal growth factor receptors (EGFR).

Other Notes

Intermediate in the synthesis of a spacer for combinatorial chemistry

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

337.5 °F

Flash Point(C)

169.7 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW2535
BCBM5598V
BCBK2255V
BCBD2137V
BCBB8779

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Polycationic adamantane-based dendrons of different generations display high cellular uptake without triggering cytotoxicity.
Grillaud M, et al.
Journal of the American Chemical Society, 136(2), 810-819 (2014)
Water soluble SERS labels comprising a SAM with dual spacers for controlled bioconjugation.
Jehn C, et al.
Physical Chemistry Chemical Physics, 11(34), 7499-7504 (2009)
Angewandte Chemie (International Edition in English), 113, 379-379 (2001)
Towards the Development of Antitumor Vaccines: A Synthetic Conjugate of a Tumor?Associated MUC1 Glycopeptide Antigen and a Tetanus Toxin Epitope.
Keil S, et al.
Angewandte Chemie (International Edition in English), 40(2), 366-369 (2001)
Phthalocyanine?peptide conjugates for epidermal growth factor receptor targeting.
Ongarora B G, et al.
Journal of Medicinal Chemistry, 55(8), 3725-3738 (2012)

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