9-Fluorenylmethanol
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9-Fluorenylmethanol

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9-Fluorenemethanol is used in the design and in the synthesis of novel type somatostatin analogs with antiproliferative activities on A431 tumor cells.

Category
Peptide Synthesis Reagents
Catalog number
BAT-002392
CAS number
24324-17-2
Molecular Formula
C14H12O
Molecular Weight
196.24
9-Fluorenylmethanol
IUPAC Name
9H-fluoren-9-ylmethanol
Synonyms
Fmoc-OH; Fluorene-9-methanol; (9H-Fluoren-9-yl)methanol; 9-(Hydroxymethyl)fluorene; 9-Fluorenylmethanol; 9-Fluorenylmethyl Alcohol; 9H-Fluorene-9-methanol; 9-Hydroxymethylfluorene; fluoren-9-ylmethan-1-ol; (9h-fluoren-9-yl)methanol; hofm
Appearance
White to light yellowish crystalline powder
Purity
≥ 99 % (HPLC)
Density
1.030 g/cm3 (Predicted)
Melting Point
105-107 °C
Boiling Point
293.1 °C (Predicted)
Storage
Store at 2-8 °C
Solubility
Slightly soluble in Chloroform, Methanol
InChI
InChI=1S/C14H12O/c15-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14-15H,9H2
InChI Key
XXSCONYSQQLHTH-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)CO
1. Facile biocatalytic access to 9-fluorenylmethyl polyglycosides: evaluation of antiviral activity on immunocompetent cells
Annabella Tramice, et al. ChemMedChem. 2008 Sep;3(9):1419-26. doi: 10.1002/cmdc.200800086.
The biological activities of a series of mono- and oligosaccharides (beta-xylosides and alpha-glucosides) of 9-fluorenylmethanol were investigated together with mono-beta-galactoside and beta-glucoside of this aglycone, produced by biocatalytic routes. By using marine glycoside hydrolases and inexpensive donors such as maltose or xylan, access to mono-alpha-glucoside or mono-beta-xyloside of 9-fluorenylmethanol was obtained. Additionally, interesting polyglycoside derivatives were isolated. Biological testing indicated that in vitro treatment with these carbohydrate derivatives may influence the balance of cytokines in the environment of human peripheral blood mononuclear cells (PBMC), restricting the harmful effect of herpes simplex type 2 replication. In fact, these carbohydrate derivatives tested in WISH cells did not show any significant antiviral activity.
2. 9-Fluorenylmethyl esters
M A Bednarek, M Bodanszky Int J Pept Protein Res. 1983 Feb;21(2):196-201. doi: 10.1111/j.1399-3011.1983.tb03093.x.
N alpha-Protected amino acid 9-fluorenylmethyl esters (Fm esters) were prepared by imidazole-catalyzed transesterification of active esters with 9-fluorenylmethanol (9-hydroxymethylfluorene). The new carboxyl protection is unaffected by acids, but is efficiently removed by beta-elimination under the influence of secondary and tertiary amines. Primary amines and ammonia can cause slight amide formation. Deblocking was achieved also by catalytic hydrogenation.
3. Photo-induced β-elimination of 9-fluorenylmethanol leading to dibenzofulvene
Hassan Nageh, Liming Zhao, Akira Nakayama, Jun-Ya Hasegawa, Yue Wang, Tamaki Nakano Chem Commun (Camb). 2017 Jul 25;53(60):8431-8434. doi: 10.1039/c7cc03297h.
An effective photo-induced β-elimination of an alcohol leading to a vinyl compound is introduced for the first time. 9-Fluorenylmethanol was irradiated in a solution using a Xe lamp and was efficiently converted to dibenzofulvene (DBF) (9-methylenefluorene) in the absence of base which is necessary in the corresponding ground-state reaction.
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