(+)-1-(9-FLUORENYL)ETHYL CHLOROFORMATE CAS No. 107474-79-3

Product Description

(+)-1-(9-Fluorenyl)ethyl chloroformate, also known as (+)-FLEC, is a chiral derivatizing reagent used in analytical chemistry for the separation and analysis of enantiomers, particularly in high-performance liquid chromatography (HPLC). (+)-FLEC features a fluorenyl group attached to an ethyl group with a chloroformate functionality, making it highly reactive with nucleophiles such as amines and alcohols. The (+) designation indicates that it is the dextrorotatory enantiomer, which rotates plane-polarized light clockwise. (+)-FLEC is typically a white or off-white crystalline solid and must be stored under anhydrous conditions due to its sensitivity to moisture. It is commonly used to derivatize amines and alcohols, forming fluorescent or UV-active diastereomers that can be easily separated and analyzed. Similar to Marfey’s reagent, (+)-FLEC enhances detection capabilities through its fluorenyl group, making it a valuable tool for enantiomeric purity determination in various applications, including HPLC and LC-MS.

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Product Use & Characteristics

Chemical Information:

• Molecular Formula: C16H13ClO2

• Molecular Weight: 272.72 g/mol

• IUPAC Name: 1-(9H-fluoren-9-yl)ethyl carbonochloridate

Structure:

• Core structure: A 9-fluorenyl group with a five-membered ring fused with two benzene rings.

• At the 9-position of the fluorenyl group, a 1-phenylethyl-type group is attached, but the "phenyl" is replaced by a fluorenyl group.

• At the 1-carbon of the ethyl group, a chloroformate group (-OCOCl) is attached.

• The "(+)-" designation indicates that this is the right-handed enantiomer of the compound, indicating chirality.

Properties:

• Physical State: Typically a solid or oily liquid, depending on purity and enantiomeric purity.

• Solubility: Freely soluble in organic solvents (such as acetone), slightly soluble in water, and readily deliquescent in water.

• Reactivity: Chloroformate groups are highly reactive and readily react with nucleophiles (such as amines and alcohols), releasing HCl and CO₂. This compound should generally be stored and used under dry conditions and away from contact with water, alcohols, and amines.

• Safety Information: Due to the presence of a reactive chloroformate group, this compound may be irritating to the skin, eyes, and respiratory tract. The reaction may liberate hydrogen chloride (HCl) gas. Handle in a fume hood and wear appropriate personal protective equipment (gloves, goggles, etc.).

Uses:

• Chiral Derivatization Reagent: One of the most well-known uses is as a chiral derivatization reagent, particularly for enantiomeric excess (ee) determination in analytical chemistry. It can react with chiral amines or alcohols to produce carbamate or carbonate derivatives with chiral centers. The resulting derivatives are diastereoisomers (if the reagent is a single enantiomer), which may have different retention times on achiral columns (such as HPLC or GC), allowing for separation and quantification.

• Protecting Groups: Chloroformate groups can be used to introduce protecting groups, such as protecting amino groups in peptide synthesis.

• Applications in Analytical Chemistry: Used in various analytical techniques including high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE) for the separation and detection of chiral compounds.

• Enantioselective Analysis: Used in the enantioselective analysis of compounds such as amino acids, biogenic amines, nucleotides, peptides, hormones, toxins, pharmaceuticals, and environmentally relevant compounds like herbicides.

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