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Merck
CN

385530

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

97%, for peptide synthesis

Synonym(s):

O-(N-Succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, TSTU

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About This Item

Empirical Formula (Hill Notation):
C9H16BF4N3O3
CAS Number:
105832-38-0
Molecular Weight:
301.05
UNSPSC Code:
12352107
PubChem Substance ID:
24864036
NACRES:
NA.22
MDL number:
MFCD00077875

Key Documents

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Product Name

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate, 97%

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

assay

97%

reaction suitability

reaction type: Coupling Reactions

mp

198-201 °C (lit.)

application(s)

peptide synthesis

functional group

amine
imide

storage temp.

2-8°C

Quality Level

300

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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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV2340
BCCG6615
BCCG7737
BCBW7170
BCBL9770V

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An efficient method for conjugation of thiamine to proteins.
Jayamani M
Bioorganic & Medicinal Chemistry Letters, 2(9), 1007-1012 (1992)
DNA minicircles with gaps for versatile functionalization.
Rasched G
Angewandte Chemie (International Edition in English), 47(5), 967-970 (2008)
Water-soluble BODIPY derivatives.
Niu S
Organic Letters, 11(10), 2049-2052 (2009)
New fluorinated rhodamines for optical microscopy and nanoscopy.
Mitronova G
Chemistry?A European Journal , 16(15), 4477-4488 (2010)
Advanced biosensing using simultaneous excitation of short and long range surface plasmons.
Slavik R
Measurement Science and Technology, 17(4), 932-932 (2006)
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