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12806

Sigma-Aldrich

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

≥97.0% (N), for peptide synthesis

Synonym(s):

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate, TBTU

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About This Item

Linear Formula:
C11H16N5O · BF4
CAS Number:
125700-67-6
Molecular Weight:
321.08
Beilstein:
7066325
MDL number:
MFCD00077413
UNSPSC Code:
12352100
PubChem Substance ID:
329749883
NACRES:
NA.21
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Product Name

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, ≥97.0% (N)

Quality Level

200

Assay

≥97.0% (N)

form

solid

mp

205 °C (dec.) (lit.)

solubility

acetonitrile: 0.1 g/mL, clear, colorless

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CN(C)\C(On1nnc2ccccc12)=[N+](/C)C

InChI

1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1

InChI key

JKEKMBGUVUKMQB-UHFFFAOYSA-N

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Application

Coupling reagent which is ideally suited for solid-phase peptide synthesis.

Other Notes

Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound[1]; Coupling reagent which is ideally suited for solid-phase peptide synthesis.[2]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H228,H317

Hazard Classifications

Flam. Sol. 1 - Skin Sens. 1A

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2606
STBK6007
WXBD7007V
STBK5204
WXBD6643V

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Rajni Bala et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 196, 268-273 (2018-02-20)
In the present study, we report a highly sensitive, rapid and low cost colorimetric monitoring of malathion (an organophosphate insecticide) employing a basic hexapeptide, malathion specific aptamer (oligonucleotide) and silver nanoparticles (AgNPs) as a nanoprobe. AgNPs are made to interact
O-(BENZOTRIAZOL-1-YL)-N, N, N', N'-TETRAMETHYLURONIUM TETRAFLUOROBORATE (TBTU): A NEW REAGENT FOR THE CLEAVAGE OF TETRAHYDROPYRANYL, SILYL AND 4, 4'-D IMETHOXYTRITYL ETHERS.
Ramasamy KS and Averett D.
Synlett, 6, 709-712 (1999)
Parvin Zakeri-Milani et al.
EXCLI journal, 16, 650-662 (2017-07-12)
Gemcitabine (Gem) is used as a single agent or in combination with other anticancer agents to treat many types of solid tumors. However, it has many limitations such as a short plasma half-life, dose-limiting toxicities and drug resistance. Cell-penetrating peptides
S. Zimmer et al. et al.
Proc. 22nd Eur. Pept. Symp.: Peptides 1992 null
Samer Al-Gharabli et al.
Materials (Basel, Switzerland), 11(5) (2018-05-08)
Advanced ceramic materials with a well-defined nano-architecture of their surfaces were formed by applying a two-step procedure. Firstly, a primary amine was docked on the ordered nanotubular ceramic surface via a silanization process. Subsequently, single-wall carbon nanotubes (SWCNTs) were covalently
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Questions

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  1. 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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  2. 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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