8.18203

(9-Fluorenylmethyl) chloroformate

for synthesis

• Synonym(s): (9-Fluorenylmethyl) chloroformate, Chloroformic acid 9-fluorenylmethyl ester, FMOCCl
• Empirical Formula (Hill Notation): C₁₅H₁₁ClO₂
• CAS Number: 28920-43-6
• Molecular Weight: 258.70
• MDL number: MFCD00001138
• UNSPSC Code: 12352108
• EC Index Number: 249-313-6
• NACRES: NA.22
• Grade: synthesis grade
• Application(s): peptide synthesis

Properties

• grade: synthesis grade
• Quality Level: 200
• form: powder
• dilution: (for synthesis)
• mp: 60-63 °C
• application(s): peptide synthesis
• storage temp.: 15-25°C
• SMILES string: ClC(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
• InChI key: IRXSLJNXXZKURP-UHFFFAOYSA-N

Description

General description

(9-Fluorenylmethyl) chloroformate, also known as Fmoc chloride, is a highly versatile reagent with varied applications in organic synthesis. It is most frequently used to introduce the base-labile Fmoc-protecting group to amine functionalities, particularly during the production of Fmoc-protected amino acids. Fmoc-chloride has also been used to generate mixed carboxylic and carbonic anhydrides to facilitate amide and ester bond formation. It is soluble in common organic solvents such as dichloromethane, tetrahydrofuran, and dimethylformamide.

Application

Recent applications of (9-Fluorenylmethyl) chloroformate include:

• (9-Fluorenylmethyl) chloroformate can be used as a coupling reagent.[1]
• In the synthesis of amino acid esters. Fmoc chloride activates the carboxylic acid group of the amino acid, allowing it to react with an alcohol to form the ester.[2]
• In the preparation of lysogangliosides.[3]
• In the solid-phase peptide synthesis of DOPA-containing peptides.[4]

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Supplementary Hazards: EUH029
• Storage Class Code: 8A - Combustible, corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable