9-bromo-9-phenyl-9H-fluorene

• ChemBase ID: 88741
• Molecular Formular: C19H13Br
• Molecular Mass: 321.21052
• Monoisotopic Mass: 320.02006242
• SMILES: BrC1(c2c(cccc2)c2c1cccc2)c1ccccc1
• Canonical SMILES: BrC1(c2ccccc2)c2ccccc2c2c1cccc2
• InChI: InChI=1S/C19H13Br/c20-19(14-8-2-1-3-9-14)17-12-6-4-10-15(17)16-11-5-7-13-18(16)19/h1-13H
• InChIKey: HYQXNCDBSALQLB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-bromo-9-phenyl-9H-fluorene
• IUPAC Traditional name: 9-bromo-9-phenylfluorene
• Synonyms: 9-Bromo-9-phenyl-9H-fluorene; 9-Bromo-9-phenylfluorene; 9-Bromo-9-phenyl-9H-fluorene; 9-Phenylfluorenyl Bromide; NSC 28079; 9-Bromo-9-phenylfluorene; 9-溴-9-苯基芴

Database IDs

• CAS Number: 55135-66-5
• EC Number: 000-000-0
• MDL Number: MFCD00075522
• Beilstein Number: 2561445
• PubChem SID: 162075652; 24862938
• PubChem CID: 231624

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.8524446
• LogD (pH = 7.4): 5.8524446
• Log P: 5.8524446
• Molar Refractivity: 88.4242 cm^3
• Polarizability: 34.525505 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: Yellow Crystalline Solid
• Melting Point: 94-99°C; 99-101 °C(lit.); 99-101°C

Safety Information

• Storage Warning: Corrosive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 26-27-28-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 96%; 97%
• Empirical Formula (Hill Notation): C19H13Br

DETAILS

Sigma Aldrich - 368873

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B686455

A bulky amine protecting reagent reported to be 6000 times more stable to acid than the trityl group.

REFERENCES

• Lee, J.H., et al.: Biosci., Biotechnol., Biochem., 68, 714 (2004)
• Lai, J.H., et al.: J. Med. Chem., 50, 2391 (2004)
• Reagent for protection of amines as their N-9-phenylfluorenyl (Pf) derivatives, which are ca 6000x more stable than trityl (Trt) groups (see Chlorotriphenylmethane, A11799) to acid hydrolysis: J. Chem. Soc., 1895 (1964), and have been found useful in asymmetric syntheses. The group has been introduced using K₃PO₄ or Et₃N as base and Pb(NO₃)₂ as a bromide scavenger: J. Org. Chem., 50, 1239 (1985); 51, 3882 (1986). An alternative lead-free method uses K₃PO₄ and nitromethane: J. Org. Chem., 58, 2369 (1993). The Pf group can be cleaved with TFA in acetonitrile. For examples and discussion, see: Org. Synth. Coll., 9, 344 (1998). Hydrogenolysis: J. Org. Chem., 60, 4602 (1995); 61, 9437 (1996), or Li/ammonia reduction: J. Org. Chem., 55, 3511 (1990) have also been reported. N-Pf- and N-Trt- derivatives of amino acids have also been converted to Leuchs' anhydrides by treatment with phosgene or triphosgene, and the products coupled with amino acid esters to give dipeptides in good yields without racemization: J. Org. Chem., 64, 2532 (1999).
• The Pf ester has also been developed for protection of the -carboxy group of glutamic acid in peptide synthesis, with better stability than trityl, but readily cleaved by TFA in DCM: Synlett, 1136 (1999).