439479

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

>95% in F+ active

• Synonym(s): N-Chloromethyl-N′-fluorotriethylenediammonium bis(tetrafluoroborate), F-TEDA
• Empirical Formula (Hill Notation): C₇H₁₄B₂ClF₉N₂
• CAS Number: 140681-55-6
• Molecular Weight: 354.26
• Beilstein/REAXYS Number: 5368649
• MDL number: MFCD00142607
• UNSPSC Code: 12352101
• PubChem Substance ID: 24867509
• NACRES: NA.22

Properties

• form: powder
• 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.)
• greener alternative category: Aligned,
• 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

Description

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.
• As a fluorinating reagent that effects oxidative ring opening of 2,5-diarylfurans to cis-1,4-enediones.
• For direct fluorination of silyl ketene acetals leading to the formation of α-fluoro-α-arylcarboxylic acids.
• As an electrophilic fluorinating reagent used. e.g. in the preparation of fluorinated acylsilanes.

Other Notes

First application of ionic liquids in electrophilic fluorination of arenes; Selectfluor (F-TEDA-BF4) for “green” fluorination.

Citation

A review.

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H302,H317,H318,H412
• pcodes: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves