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900400

Sigma-Aldrich

SLAP 3-SpiroCyHex N-Bn Pip Reagent

≥95%

Synonym(s):

1-((Benzyl((trimethylsilyl)methyl)amino)methyl)cyclohexanamine

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About This Item

Empirical Formula (Hill Notation):
C18H32N2Si
Molecular Weight:
304.55
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

Assay

≥95%

form

liquid

refractive index

n/D 1.516

density

0.956 g/mL

storage temp.

−20°C

InChI

1S/C18H32N2Si/c1-21(2,3)16-20(14-17-10-6-4-7-11-17)15-18(19)12-8-5-9-13-18/h4,6-7,10-11H,5,8-9,12-16,19H2,1-3H3

InChI key

HHDPYUUHZQUCNL-UHFFFAOYSA-N

Application

Silicon amine protocol (SLAP) reagents, in conjunction with aldehydes and ketones, form N-unprotected piperazines via photocatalytic cross-coupling with Ir[(ppy)2dtbbpy]PF6 (747769). Heteroaromatic, aromatic, and aliphatic aldehydes are well tolerated, as are structurally and stereochemically complex SLAP reagents. This product was introduced in collaboration with the Bode Research Group and provides a tin-free alternative to SnAP (tin amine protocol) reagents for piperazine synthesis.

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Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3


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Stephen B Milne et al.
Nature chemical biology, 6(3), 205-207 (2010-01-26)
Alkyne-modified phospholipids can be unambiguously identified and differentiated from native species in complex mixtures by formation of dicobalthexacarbonyl complexes. This reaction is specific for alkynes and is unaffected by other glycerophospholipid-related moieties. Enrichment of cells with alkyne-derivatized fatty acids or
Xinxin Gao et al.
FEBS letters, 585(15), 2501-2506 (2011-07-12)
Palmitoylation of the Wnt and Hedgehog proteins is critical for maintaining their physiological functions. To date, there are no reported studies that characterize the cellular distribution of the palmitoylated forms of these proteins. Here, we describe the subcellular localization of
Christoph Thiele et al.
ACS chemical biology, 7(12), 2004-2011 (2012-09-25)
Fatty acids are abundant constituents of all biological systems, and their metabolism is important for normal function at all levels of an organism. Aberrations in fatty acid metabolism are associated with pathological states and have become a focus of current
Megan C Yap et al.
Journal of lipid research, 51(6), 1566-1580 (2009-12-24)
Progress in understanding the biology of protein fatty acylation has been impeded by the lack of rapid direct detection and identification methods. We first report that a synthetic omega-alkynyl-palmitate analog can be readily and specifically incorporated into GAPDH or mitochondrial
Keri A Tallman et al.
Journal of lipid research, 54(3), 859-868 (2013-01-12)
Monitoring lipid distribution and metabolism in cells and biological fluids poses many challenges because of the many molecular species and metabolic pathways that exist. This study describes the synthesis and study of molecules that contain an alkyne functional group as

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