(9H-Fluoren-9-yl)-methyl chloroformate, CAS No. 28920-43-6

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28920-43-6

Catalog No. EBD49547

CAS 28920-43-6

Name (9H-Fluoren-9-yl)-methyl chloroformate

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Basic Information

Synonyms: 9-Fluorenylmethylchloroformate 9-Fluorenylmethyloxycarbonylchloride FMOC-chloride Fmoc-Cl Chloroformicacid9-fluorenylmethylester 9-Fluorenylmethoxycarbonyl 9H-fluoren-9-ylmethylcarbonochloridate 9-Fluorenylmethoxycarbonylchloride 9-Fmocchloride (9H-Fluoren-9-yl)-methylchloroformate 9h-fluoren-9-ylmethylchloroformate

Molecular Formula: C15H11ClO2

Molecular Weight: 258.7

MDL Number: MFCD00001138

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Protecting and Deprotecting Reagents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

(9H-Fluoren-9-yl)-methyl chloroformate, commonly known as Fmoc-Cl, is a chloroformate derivative of 9-fluorenylmethanol. It is a white to off-white crystalline solid with a molecular weight of 258.70 g/mol. The compound features a highly reactive chloroformate group attached to a bulky, aromatic fluorenylmethyl moiety, which provides strong UV absorbance for easy monitoring. Its primary and most significant application is as a protecting reagent for primary and secondary amines in peptide synthesis. Fmoc-Cl reacts with the amino group to form a stable carbamate (Fmoc-protected amine), which is base-labile and can be selectively removed under mild conditions using a secondary amine like piperidine. This orthogonal protection strategy is fundamental to the widely used Fmoc/tBu solid-phase peptide synthesis (SPPS) methodology. Beyond peptide chemistry, it is also employed as a derivatization reagent for the analysis of amines and amino acids in HPLC and mass spectrometry due to its excellent chromophoric properties.

Physical Properties

Melting Point: 61-64 °C

Boiling Point: 393.9 °C at 760 mmHg

Flash Point: 143.6 °C

Density: 1.288 g/cm3

Solubility: dioxane: 0.1 g/mL, clear, colorless

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 3261

Analytical Data

Appearance: white to off-white powder