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04936

Sigma-Aldrich

O-(6-Chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

≥98.0% (HPLC)

Synonym(s):

1-[Bis(dimethylamino)methylen]-5-chlorobenzotriazolium 3-oxide hexafluorophosphate, N,N,N′,N′-Tetramethyl-O-(6-chloro-1H-benzotriazol-1-yl)uronium hexafluorophosphate, HCTU

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About This Item

Empirical Formula (Hill Notation):
C11H15ClF6N5OP
CAS Number:
330645-87-9
Molecular Weight:
413.69
MDL number:
MFCD04973268
UNSPSC Code:
12352101
PubChem Substance ID:
329747994
NACRES:
NA.22

Quality Level

200

Assay

≥98.0% (HPLC)

form

powder

reaction suitability

reaction type: Coupling Reactions

impurities

≤0.5% water

mp

185-190 °C

application(s)

peptide synthesis

functional group

amine
chloro

SMILES string

ClC1=CC=C(N([C+](N(C)C)N(C)C)N=[N+]2[O-])C2=C1.F[P-](F)(F)(F)(F)F

InChI

1S/C11H15ClN5O.F6P/c1-15(2)11(16(3)4)18-17-10-7-8(12)5-6-9(10)13-14-17;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1

InChI key

ZHHGTMQHUWDEJF-UHFFFAOYSA-N

Application

Reagent for:
Synthesis of near-infrared pH activatable fluorescent probes
Synthesis of human β-amyloid by Fmoc chemistry
Stereoselective Horner-Wadsworth-Emmons olefination
Covalent ligation of fluorescent peptides to quantum dots
Alkylation of human telomere sequence

Other Notes

Tandem Oligonucleotide Synthesis on Solid-Phase Supports for the Production of Multiple Oligonucleotides

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6682
BCCD7640
BCBZ3421
BCBT4008
BCBR0407V

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Juan B Blanco-Canosa et al.
Journal of the American Chemical Society, 132(29), 10027-10033 (2010-07-06)
Water solubilized nanoparticles such as CdSe-ZnS core-shell nanocrystals (quantum dots, QDs) have great potential in bioimaging and sensing applications due to their excellent photophysical properties. However, the efficient modification of QDs with complex biomolecules represents a significant challenge. Here, we
Wouter A van der Linden et al.
Organic & biomolecular chemistry, 8(8), 1885-1893 (2010-05-08)
The synthesis and biological evaluation of ten Michael acceptors containing potential proteasome inhibitors are described. Cellular targets of azide containing inhibitors and were assessed in HEK293T and RAW264.7 cells by a two step labeling strategy, followed by biotin-pulldown, affinity purification
Hyeran Lee et al.
Bioconjugate chemistry, 22(4), 777-784 (2011-03-11)
Highly tumor selective near-infrared (NIR) pH-activatable probe was developed by conjugating pH-sensitive cyanine dye to a cyclic arginine-glycine-aspartic acid (cRGD) peptide targeting α(v)β(3) integrin (ABIR), a protein that is highly overexpressed in endothelial cells during tumor angiogenesis. The NIR pH-sensitive
Amit Kumar Tripathi et al.
Scientific reports, 7(1), 3384-3384 (2017-06-15)
Marine fish antimicrobial peptide, chrysophsin-1 possesses versatile biological activities but its non-selective nature restricts its therapeutic possibilities. Often small alterations in structural motifs result in significant changes in the properties of concerned proteins/peptides. We have identified GXXXXG motif in chrysophsin-1.
Gengo Kashiwazaki et al.
Bioorganic & medicinal chemistry, 18(8), 2887-2893 (2010-03-31)
We designed and synthesized human telomere alkylating N-methylpyrrole-N-methylimidazole (PI) polyamide conjugates (1-6). The C-type conjugates 1-3 possessed a chlorambucil moiety at the C terminus, whereas the N-type conjugates 4-6 had one of these moieties at the N terminus. The DNA
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