2-Bromo-1-ethylpyridinium tetrafluoroborate Chemical Properties

Melting point:

103-107 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Crystalline Powder

color 

White

Water Solubility 

very faint turbidity

BRN 

4059265

Major Application

peptide synthesis

InChI

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

InChIKey

YJDXVQLBIAJTHP-UHFFFAOYSA-N

SMILES

[N+]1(CC)C=CC=CC=1Br.[B-](F)(F)(F)F

CAS DataBase Reference

878-23-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36/37/39-26

RIDADR 

1759

WGK Germany 

3

F 

9-21

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29333990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

2-Bromo-1-ethylpyridinium tetrafluoroborate Usage And Synthesis

Uses

2-Bromo-1-ethylpyridinium Tetrafluoroborate is a carboxyl activation and coupling reagent for peptide synthesis.

Uses

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.

reaction suitability

reaction type: Coupling Reactions

Synthesis

Procedure: trifluoroacetic acid (9.2 ml, 12.0 mg molecule) was added to a solution (3.00 g, 12.0 mg molecule) of N-Boc-N-methyl-L-leucine methyl ester (50 ml) at -20??C. This mixture was heated to room temperature and stirred for 2 h. The aqueous layer was extracted with CH2Cl2 (2x) over Na2SO4 in order to structure and neutralize the carefully sat. aq. NaHCO3. the aqueous layer was extracted with CH2Cl2 (2x) and said composite organic layer was dried over Na2SO4. After solvent removal in evacuation, the free amine was dissolved in dry CH2Cl2 (50 mL) and N-Cbz-(L)-valine (3.32 g, 13.2 mmol) and DIEA (4.1 mL, 24.0 mmol) were added. Then, a small amount of BEP (3.61 g, 13.2 mmol) was added at room temperature to obtain a yellow solution. It was stirred overnight, diluted with CH2Cl2, and then washed with 1 mol /L aq. KHSO4, sataq . NaHCO3 and brine to wash. The solvent (Na2SO4) was removed after drying and the residue was purified by column chromatography (silica gel, PE:EtOAc 8:2). Dipeptide 1 (4.08 g, 10.4 mmol, 87%) was a colorless resin.

2-Bromo-1-ethylpyridinium tetrafluoroborate(878-23-9)Related Product Information

• Fluoroboric acid
• 4-BROMO-2,2-DIPHENYLBUTYRONITRILE
• 3-Bromoanisole
• 2-Pyridineboronic acid
• Sodium 2-bromoethanesulphonate
• 4-Ethylpyridine
• 1-Hexadecylpyridinium bromide
• Pyridine-4-boronic acid
• Ethylboronic acid
• 3-Pyridylboronic acid
• 1-ethylpyridine trifluoroacetate
• Hydroxyethyl imidazole
• 3-Ethylpyridine
• 2-Ethylpyridine
• 2-Bromopyridine
• Ethylamine-borontrifluoride
• 2-Bromo-1-ethylpyridinium tetrafluoroborate