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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

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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

Related Categories

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

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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New fluorinated rhodamines for optical microscopy and nanoscopy.
Mitronova G
Chemistry?A European Journal , 16(15), 4477-4488 (2010)
DNA minicircles with gaps for versatile functionalization.
Rasched G
Angewandte Chemie (International Edition in English), 47(5), 967-970 (2008)
An efficient method for conjugation of thiamine to proteins.
Jayamani M
Bioorganic & Medicinal Chemistry Letters, 2(9), 1007-1012 (1992)
Multi-analyte surface plasmon resonance biosensing.
Homola J
Methods, 37(1), 26-36 (2005)
A simplified protocol for the automated production of succinimidyl 4?[18F] fluorobenzoate on an IBA Synthera module.
Ackermann U
Journal of Labelled Compounds & Radiopharmaceuticals, 54(10), 671-673 (2011)
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