9-Fluorenylmethanol acts as a N-protecting reagent, which is used in the synthesis of peptide. It is also used in the preparation of deoxynucleoside 9-fluorenemethyl phosphorodithioates. Further, it is used to prepare 9-(fluoromethyl)fluorene. In addition to this, it is involved in the electropolymerization with boron trifluoride diethyl etherate to yield low-potential electrodeposition of semiconducting poly(9-fluorenemethanol) film.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
9-Fluorenylmethanol acts as a N-protecting reagent, which is used in the synthesis of peptide. It is also used in the preparation of deoxynucleoside 9-fluorenemethyl phosphorodithioates. Further, it is used to prepare 9-(fluoromethyl)fluorene. In addition to this, it is involved in the electropolymerization with boron trifluoride diethyl etherate to yield low-potential electrodeposition of semiconducting poly(9-fluorenemethanol) film.
Solubility
Soluble in methanol.
Notes
Incompatible with strong oxidizing agents.
RUO – Research Use Only
Reagent for protection of carboxyl groups as their 9-fluorenylmethyl (Fm) esters, which improve solubility of the molecule in organic solvents. Fm esters can be formed, e.g. by the DCC-DMAP method: Tetrahedron Lett., 24, 281 (1983), or by imidazole-catalyzed transesterification of active esters of N-protected amino acids: Int. J. Pept. Prot. Res., 21, 196 (1983). Cleavage is by hydrogenolysis. See Appendix 6.
Can also be used to protect phosphate groups in oligonucleotide synthesis: J. Chem. Soc., Chem. Commun., 803 (1973).
Arimitsu, K.; Kumazawa, Y.; Furutani, M. Preparation of base-amplifying microcapsules and their application to photoreactive materials. J. Polym. Sci., Part A: Polym. Chem. 2015, 53 (21), 2440-2443.
Furutani, M.; Kobayashi, H.; Gunji, T.; Abe, Y.; Arimitsu, K. Base-amplifying silicone resins with photobase-generating side chains and their application to negative-working photoresists. J. Polym. Sci., Part A: Polym. Chem. 2015, 53 (10), 1205-1212.