CAS 55135-66-5|9-Bromo-9-phenyl-9H-fluorene|9-bromo-9-phenyl-9H-fluorene|9-bromo-9-phenylfluorene|9-Bromo-9-phenylfluorene|9-溴-9-苯基芴|NSC 28079|9-Phenylfluorenyl Bromide|9-Bromo-9-phenyl-9H-fluor...

General Information

Structure

Molecular Formula

C₁₉H₁₃Br

Molecular Mass

321.21052

Exact Mass

320.02006242

Charge

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

Canonic Smiles

BrC1(c2ccccc2)c2ccccc2c2c1cccc2

Isomeric Smiles

BrC1(c2c(cccc2)c2c1cccc2)c1ccccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

5.8524446

LogD (pH = 7.4)

5.8524446

Log P

5.8524446

Molar Refractivity

88.4242

Polarizability

34.525505

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

9-Bromo-9-phenyl-9H-fluorene9-溴-9-苯基芴9-Bromo-9-phenylfluorene9-Phenylfluorenyl BromideNSC 280799-Bromo-9-phenylfluorene9-Bromo-9-phenyl-9H-fluorene

IUPAC name

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

IUPAC Traditional name

9-bromo-9-phenylfluorene

Names and Identifiers

Registration numbers

MDL Number

CAS Number

PubChem SID

Beilstein Number

EC Number

PubChem CID

Registration numbers

Properties

Product Information

Empirical Formula (Hill Notation)

C19H13Br

Purity

97%

96%

Certificate of Analysis

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Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

368873

Packaging
1, 5 g in glass bottle

TRC

B686455

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

Molecule Details

References

PubChem Literature

From Data Sources

• Lee, J.H., et al.: Biosci., Biotechnol., Biochem., 68, 714 (2004)

• Lai, J.H., et al.: J. Med. Chem., 50, 2391 (2004)

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity