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15406

Sigma-Aldrich

N-Boc-cadaverine

≥97.0% (NT)

Synonym(s):

N-Boc-1,5-diaminopentane, tert-Butyl N-(5-aminopentyl)carbamate

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About This Item

Linear Formula:
(CH)3COCONH(CH2)5NH2
CAS Number:
51644-96-3
Molecular Weight:
202.29
Beilstein:
3603658
MDL number:
MFCD00210020
UNSPSC Code:
12352200
PubChem Substance ID:
57647414
NACRES:
NA.22

Quality Level

200

Assay

≥97.0% (NT)

reaction suitability

reagent type: cross-linking reagent

refractive index

n20/D 1.460

density

0.972 g/mL at 20 °C (lit.)

functional group

Boc
amine

SMILES string

NCCCCCNC(OC(C)(C)C)=O

InChI

1S/C10H22N2O2/c1-10(2,3)14-9(13)12-8-6-4-5-7-11/h4-8,11H2,1-3H3,(H,12,13)

InChI key

DPLOGSUBQDREOU-UHFFFAOYSA-N

Application

Some of the reported applications of N-Boc-cadaverine include:
  • Synthesis of of a supermacrocycle that self-assemble to form organic nanotubes.
  • Preparation of water-soluble unsymmetrical sulforhodamine fluorophores from monobrominated sulfoxanthene dye.
  • Synthesis of functionalized porphyrins as biocompatible carrier system for photodynamic therapy (PDT).

Other Notes

Building block for preparing polyamines and polyamides

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

228.2 °F - closed cup

Flash Point(C)

109.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB7735
BCBC8355V
BCBC8355
BCBS8337V
1356882

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T. Teshima et al.
Tetrahedron, 47, 3305-3305 (1991)
C Melchiorre et al.
Journal of medicinal chemistry, 32(1), 79-84 (1989-01-01)
Several polymethylene tetraamines related to methoctramine (1) were prepared and evaluated for their blocking activity on M-2 muscarinic receptors in guinea pig atria and ileum. It turned out that antimuscarinic potency depends on the following parameters: (a) nature of the
A toolset of functionalized porphyrins with different linker strategies for application in bioconjugation.
Staegemann M H, et al.
Organic & Biomolecular Chemistry, 14(38), 9114-9132 (2016)
Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye.
Chevalier A, et al.
European Journal of Organic Chemistry, 2015(1), 152-165 (2015)
Helical rosette nanotubes: design, self-assembly, and characterization.
Fenniri H, et al.
Journal of the American Chemical Society, 123(16), 3854-3855 (2001)
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Articles

MRT - Mono-Boc-Protection of Diamines

Mono-Boc-protected diamines are versatile building blocks for chemical synthesis. Their production is a lot more challenging than the simple reaction scheme might imply, because the Boc-anhydride reagent cannot differentiate between the two identical amino moieties in the substrate.

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