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Sigma-Aldrich

N-Boc-1,4-butanediamine

≥97.0% (GC/NT)

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Synonym(s):
N-Boc-1,4-diaminobutane, tert-Butyl N-(4-aminobutyl)carbamate
Linear Formula:
(CH3)3COCONH(CH2)4NH2
CAS Number:
Molecular Weight:
188.27
Beilstein/REAXYS Number:
1937878
MDL number:
PubChem Substance ID:

Quality Level

assay

≥97.0% (GC/NT)

reaction suitability

reagent type: cross-linking reagent

refractive index

n20/D 1.460

density

0.984 g/mL at 20 °C (lit.)

functional group

Boc
amine

SMILES string

NCCCCNC(OC(C)(C)C)=O

InChI

1S/C9H20N2O2/c1-9(2,3)13-8(12)11-7-5-4-6-10/h4-7,10H2,1-3H3,(H,11,12)

InChI key

ZFQWJXFJJZUVPI-UHFFFAOYSA-N

Application

  • Carboxy-Silane Coated Iron Oxide Nanoparticles: Details the application of N-Boc-1,4-butanediamine in modifying iron oxide nanoparticles for imaging and drug delivery (D Stanicki, S Boutry, S Laurent, et al., 2014). Access the article.

Other Notes

Preparation of pharmacologically active compounds. Preparation of spermidine analogues. Introduction of a C4-spacer.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

228.2 °F - closed cup

flash_point_c

109.0 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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L I Kruse et al.
Journal of medicinal chemistry, 32(2), 409-417 (1989-02-01)
In an attempt to identify a soluble oncodazole analogue that could be easily formulated, a series of substituted oncodazoles was synthesized and evaluated for tubulin binding affinity, in vitro cytotoxicity against cultured mouse B-16 cells, and ability to prolong lifespan
Anand Divakaran et al.
Journal of medicinal chemistry, 61(20), 9316-9334 (2018-09-27)
As regulators of transcription, epigenetic proteins that interpret post-translational modifications to N-terminal histone tails are essential for maintaining cellular homeostasis. When dysregulated, "reader" proteins become drivers of disease. In the case of bromodomains, which recognize N-ε-acetylated lysine, selective inhibition of
Shaohui Deng et al.
Science advances, 6(29), eabb4005-eabb4005 (2020-08-25)
Controlled release of CRISPR-Cas9 ribonucleoprotein (RNP) and codelivery with other drugs remain a challenge. We demonstrate controlled release of CRISPR-Cas9 RNP and codelivery with antitumor photosensitizer chlorin e6 (Ce6) using near-infrared (NIR)- and reducing agent-responsive nanoparticles in a mouse tumor
Y Shai et al.
Biochemistry, 28(11), 4801-4806 (1989-05-30)
In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential
Regina Holm et al.
Macromolecular rapid communications, 36(23), 2083-2091 (2015-09-08)
In this work, the synthesis of polypeptoid-block-polypeptide copolymers (block copolypept(o)ides) based on bifunctional initiators is described, which introduces a distinct chemical entity at the connection between both blocks. With a view towards redox-sensitive block copolypept(o)ides, a cystamine-based initiator was used

Articles

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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