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55135-66-5 - 9-Bromo-9-phenylfluorene, 96% - L14225 - Alfa Aesar

L14225 9-Bromo-9-phenylfluorene, 96%

CAS Number
55135-66-5
Synonyms

Size Price ($) Quantity Availability
1g 38.16
5g 127.60
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9-Bromo-9-phenylfluorene, 96%

MDL
MFCD00075522
EINECS
000-000-0

Chemical Properties

Formula
C19H13Br
Formula Weight
321.23
Melting point
94-99°

Literature References

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).

/n

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).

/n

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2561445
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2903.99
TSCA
No

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