8.18203

(9-Fluorenylmethyl) chloroformate

for synthesis

• Sinónimos: (9-Fluorenylmethyl) chloroformate, Chloroformic acid 9-fluorenylmethyl ester, FMOCCl
• Fórmula empírica (notación de Hill): C₁₅H₁₁ClO₂
• Número de CAS: 28920-43-6
• Peso molecular: 258.70
• Número MDL: MFCD00001138
• Código UNSPSC: 12352108
• Número índice de la CE: 249-313-6
• NACRES: NA.22
• aplicaciones: peptide synthesis

Propiedades

• Nivel de calidad: 200
• Formulario: powder
• mp: 60-63 °C
• aplicaciones: peptide synthesis
• temp. de almacenamiento: 15-25°C
• cadena SMILES: 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
• Clave InChI: IRXSLJNXXZKURP-UHFFFAOYSA-N

Descripción

Descripción general

(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.

Aplicación

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]

Información de seguridad

• Pictogramas: GHS05
• Palabra de señalización: Danger
• Frases de peligro: H314
• Consejos de prudencia: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Clasificaciones de peligro: Eye Dam. 1 - Skin Corr. 1B
• Riesgos supl.: EUH029
• Código de clase de almacenamiento: 8A - Combustible, corrosive hazardous materials
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable