9H-fluoren-9-ylmethanol

• ChemBase ID: 70040
• Molecular Formular: C14H12O
• Molecular Mass: 196.24448
• Monoisotopic Mass: 196.088815
• SMILES: C1(c2ccccc2c2ccccc12)CO
• Canonical SMILES: OCC1c2ccccc2c2c1cccc2
• 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
• InChIKey: XXSCONYSQQLHTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9H-fluoren-9-ylmethanol
• IUPAC Traditional name: 9H-fluorene-9-methanol
• Synonyms: 9-(Hydroxymethyl)fluorene; 9-Fluorenylmethanol; 9-Fluorenemethanol; 9H-(Fluoren-9-yl)methanol; 9-(Hydroxymethyl)-9H-fluorene; 9-Fluorenemethanol; 9-Fluorenemethanol; 9-Fluorenylmethanol; 9-(羟甲基)芴; 9-芴基甲醇; 9-芴甲醇

Database IDs

• CAS Number: 24324-17-2
• EC Number: 246-167-5
• MDL Number: MFCD00001139
• Beilstein Number: 2330017
• PubChem SID: 162035765; 24849874
• PubChem CID: 90466

CALCULATED PROPERTIES

• Acid pKa: 15.227866
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.6673136
• LogD (pH = 7.4): 2.6673136
• Log P: 2.6673136
• Molar Refractivity: 61.2737 cm^3
• Polarizability: 24.88023 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 102-105 °C; 102-106°C; 102-107°C; 105-107 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C14H12O

DETAILS

Sigma Aldrich - 160504

Packaging
10, 50 g in glass bottle
Application
N-protecting reagent1 for use in peptide syntheses.2,3

Sigma Aldrich - 46915

Other Notes
Phosphate protecting group in the synthesis of deoxyribo-oligonucleotides1; Carboxy protecting group2,3,4

REFERENCES

• 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).