878-23-9

Basic information

• Product Name: 2-Bromo-1-ethylpyridinium tetrafluoroborate
• Synonyms: bromoethylpyridiniumtetrafluoroborate;BEP TETRAFLUOROBORATE;2-BROMO-1-ETHYLPYRIDINIUM TETRAFLUOROBORATE;BEPyBr ;2-BROMO-1-ETHYLPYRIDINIUM TETRAFLUOROBORATE (BEP);2-Bromo-1-ethylpyridinium tetrafluoroborate 98%;2-Bromo-1-ethylpyridiniumtetrafluoroborate98%;2-BROMO-1-ETHYLPYRIDINIUM TETRAFLUOROBOR
• CAS NO: 878-23-9
• Molecular Formula: BF₄*C₇H₉BrN
• Molecular Weight: 273.86
• EINECS: 212-900-2
• Product Categories: B (Classes of Boron Compounds);Condensation & Active Esterification;Pyridinium Compounds;Synthetic Organic Chemistry;Tetrafluoroborates
• Mol File: 878-23-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 102-104 °C
• Appearance: White/Crystalline Powder
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: very faint turbidity
• BRN: 4059265
• CAS DataBase Reference: 2-Bromo-1-ethylpyridinium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-1-ethylpyridinium tetrafluoroborate(878-23-9)
• EPA Substance Registry System: 2-Bromo-1-ethylpyridinium tetrafluoroborate(878-23-9)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36/37/39-26
• RIDADR: 1759
• WGK Germany: 3
• F: 9-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 878-23-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 878-23-9 differently. You can refer to the following data:
1. 2-Bromo-1-ethylpyridinium Tetrafluoroborate is a carboxyl activation and coupling reagent for peptide synthesis.
2. 2-Bromo-1-ethyl-pyridinium tetrafluoroborate can be used as a coupling reagent for:The synthesis of N-methylated peptides in solution and solid phase.The synthesis of cyclosporin A fragment and dolastatin 15 pentapeptide moiety.

General Description

2-Bromo-1-ethyl-pyridinium tetrafluoroborate is a coupling reagent employed in the synthesis of amides and esters through amidation and esterification reactions, respectively. It is generally prepared by the reaction of triethyloxonium tetrafluoroborate with 2?bromo pyridine.

InChI:InChI=1/C7H9BrN.BF4/c1-2-9-6-4-3-5-7(9)8;2-1(3,4)5/h3-6H,2H2,1H3;/q+1;-1

Upstream product

• 109-04-6 2-bromo-pyridine 
• 368-39-8 triethyloxonium fluoroborate 

Downstream Products

• 76-05-1 trifluoroacetic acid 
• 120205-52-9 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 

Relevant articles and documents

Toward breast cancer resistance protein (BCRP) inhibitors: design, synthesis of a series of new simplified fumitremorgin C analogues

In this study, we report the design and synthesis of a series of new simplified fumitremorgin C analogues. The preliminary biological study indicated some of these simplified fumitremorgin C might be developed into breast cancer resistance inhibitors.

Total synthesis of cyclosporin O both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP

Cyclosporin O (1), an extensively N-methylated immunosuppressive cyclic undecapeptide isolated from Tolypocladium inflatum Gams, was synthesized in 20-23% overall yield via 4 + 7 segment condensation and cyclization by the combined utilization of novel thiazolium- and immonium-type peptide coupling reagents 2-bromo-3-ethyl-4-methyl thiazolium tetrafluoroborate (BEMT) and 5- (1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate (BDMP) as well as compound 2-bromo-1-ethyl pyridinium tetrafluoroborate (BEP). BEMT and BEP, which have been proven to be very efficient for the coupling of peptide segments containing N-alkylated amino acid residues with respect to the fast reaction speed, low racemization, and high yields, were used to construct hindered amide bonds in CsO with the addition of HOAt, whereas the most efficient HOBt-derived immonium type reagent, BDMP, was used to perform the coupling of coded amino acids in CsO. Thus, the highly hindered protected 8-11 tetrapeptide 25 was successfully synthesized using BEMT in 65% yield, and the 1-7 heptapeptide 21 was obtained in 52-55% yield by the rationally combined utilization of BDMP, BEMT, and BEP. The synthesis of the linear undecapeptide 27 of CsO in the solid phase using BEMT and BEP was accomplished for the further evaluation of the effectiveness of these reagents.