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385530

Sigma-Aldrich

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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¥6,330
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¥9,440

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About This Item

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

¥6,330

Available to ship onApril 14, 2025Details

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Product Name

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

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

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.[1][2]

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.[3][4][5] 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.[6][7][8]
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

JAN Code

385530-1G:4548173142265
385530-VAR:
385530-5G:4548173142272
385530-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV2340
BCCG6615
BCCG7737
BCBW7170
BCBL9770V

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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)
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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