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385530

Sigma-Aldrich

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate

97%, for peptide synthesis

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Synonym(s):
O-(N-Succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, TSTU
Empirical Formula (Hill Notation):
C9H16BF4N3O3
CAS Number:
105832-38-0
Molecular Weight:
301.05
MDL number:
MFCD00077875
UNSPSC Code:
12352107
PubChem Substance ID:
24864036
NACRES:
NA.22

Quality Level

300

Assay

97%

reaction suitability

reaction type: Coupling Reactions

mp

198-201 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CN(C)C(\ON1C(=O)CCC1=O)=[N+](\C)C

InChI

1S/C9H16N3O3.BF4/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;2-1(3,4)5/h5-6H2,1-4H3;/q+1;-1

InChI key

YEBLHMRPZHNTEK-UHFFFAOYSA-N

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General description

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate is commonly used for the conversion of carboxylic acid into the corresponding N-hydroxysuccinimidyl (NHS) ester.

Application

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate may be used in the synthesis of N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB), a 18F-labeled agent used for labeling biomarkers. it may also be used for the activation of carboxylic group of C16-chained alkanethiols that are used in developing surface plasmon resonance (SPR) sensors.
Reactant for:
Linking sensor molecules with amino groups to amino functionalized AFM tips

Reactant for synthesis of:
A polymer supported oranotin reagent for prosthetic group labeling of biological macromolecules with radioiodine
L-Rhamnose antigen
Fluorinated rhodamines for optical microscopy and nanoscopy
c(RGDyK) targeted SN38 prodrug
Polyelectrolytes for thin film construction

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A facile automated synthesis of N?succinimidyl 4?[18F] fluorobenzoate ([18F] SFB) for 18F?labeled cell?penetrating peptide as PET tracer.
Tang G
Journal of Labelled Compounds & Radiopharmaceuticals, 53(8), 543-547 (2010)
Facile synthesis of N?succinimidyl 4?[18F] fluorobenzoate ([18F] SFB) for protein labeling.
Tang G
Journal of Labelled Compounds & Radiopharmaceuticals, 51(1), 68-71 (2008)
Compact and low-cost biosensor based on novel approach to spectroscopy of surface plasmons.
Piliarik M
Biosensors And Bioelectronics, 24(12), 3430-3435 (2009)
N-Succinimidyl 4-[18 F]-fluoromethylbenzoate-labeled dimeric RGD peptide for imaging tumor integrin expression.
Li W
Amino Acids, 43(3), 1349-1357 (2012)
Oxidative DNA damage through long-range electron transfer.
Hall D
Nature, 82(6593), 731-731 (1996)
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