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439479

Sigma-Aldrich

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

greener alternative

>95% in F+ active

Synonym(s):

N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate), F-TEDA

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€133.00
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Estimated to ship on29 March 2025


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5 G
€40.50
25 G
€133.00
100 G
€215.00

About This Item

Empirical Formula (Hill Notation):
C7H14B2ClF9N2
CAS Number:
Molecular Weight:
354.26
Beilstein:
5368649
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

€40.50


Estimated to ship on29 March 2025


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form

powder

Quality Level

reaction suitability

reagent type: catalyst
reagent type: oxidant
reaction type: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

concentration

>95% in F+ active

mp

260 °C (lit.)

functional group

chloro

greener alternative category

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2

InChI

1S/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1

InChI key

TXRPHPUGYLSHCX-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is a fluorine donor also called Selectfluor and has been enhanced for catalysis. Find details here.

Application

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is an electrophilic fluorinating reagent used for greener fluorination of acetoacetamides in PEG-400.
Catalyst-free and highly selective electrophilic mono-fluorination of acetoacetamides: facile and efficient preparation of 2-fluoroacetoacetamides in PEG-400

It can be used:
  • As a highly effective and versatile source of electrophilic fluorine.[1]
  • As a fluorinating reagent that effects oxidative ring opening of 2,5-diarylfurans to cis-1,4-enediones.[2]
  • For direct fluorination of silyl ketene acetals leading to the formation of α-fluoro-α-arylcarboxylic acids.[3]
  • As an electrophilic fluorinating reagent used. e.g. in the preparation of fluorinated acylsilanes.[4]

Citation

A review.[5]

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Rajendra P Singh et al.
Accounts of chemical research, 37(1), 31-44 (2004-01-21)
Synthetic and structural aspects of organofluorine compounds continue to be the focal points of vigorous research activities, as evidenced by the appearance of a large number of publications. Among the various useful methodologies for the introduction of fluorine into organic
Oxidative ring opening of 2, 5-diarylfurans by Selectfluor
Blank SJ and Stephens CE
Tetrahedron Letters, 47(38), 6849-6850 (2006)
A novel general method for preparation of a-fluoro-a-arylcarboxylic acid. Direct fluorination of silyl ketene acetals with Selectfluor
Zhang F and Song JZ
Tetrahedron Letters, 47(43), 7641-7644 (2006)
Paul T Nyffeler et al.
Angewandte Chemie (International ed. in English), 44(2), 192-212 (2004-12-04)
The replacement of hydrogen atoms with fluorine substituents in organic substrates is of great interest in synthetic chemistry because of the strong electronegativity of fluorine and relatively small steric footprint of fluorine atoms. Many sources of nucleophilic fluorine are available
A general method for synthesis of trifluoroacetyltrialkyl (aryl) silanes and the Sakurai reaction of fluorinated acylsilanes with allyl silanes
Chung WJ and Welch JT
Journal of Fluorine Chemistry, 125(4), 543-548 (2004)

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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