Misplaced Pages

9-Methylene-fluorene

Names
Preferred IUPAC name 9-Methylidene-9H-fluorene
Other names Methylenefluorene 9-Methylidenefluorene Dibenzofulvene
Identifiers
CAS Number	4425-82-5
3D model (JSmol)	Interactive image
ChemSpider	70523
ECHA InfoCard	100.251.583
PubChem CID	78147
UNII	9299E1P3CC
CompTox Dashboard (EPA)	DTXSID90196082
InChI InChI=1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2Key: ZYASLTYCYTYKFC-UHFFFAOYSA-N
SMILES C=C1C2=CC=CC=C2C3=CC=CC=C13
Properties
Chemical formula	C14H10
Molar mass	178.234 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

9-Methylene-fluorene or dibenzofulvene (DBF) is a polycyclic aromatic hydrocarbon with chemical formula (C₆H₄)₂C=CH₂. It is best known as one product from deprotection of the Fmoc group. It can be prepared by treatment of 9-hydroxymethylfluorene with strong base.

Properties

It is an analog of a 1,1-diphenylethylene. Polymerization of 9-methylene-fluorene produces a π-stacked polymer.

See also

• Fluorene
• Fluorenylmethyloxycarbonyl chloride
• Fluorenylidene

References

1. Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404–3409. doi:10.1021/jo00795a005.
2. Nakano, Tamaki; Nakagawa, Osamu; Yade, Tohru; Okamoto, Yoshio (2003). "Solid-State Polymerization of Dibenzofulvene Leading to a Copolymer with Oxygen". Macromolecules. 36 (5): 1433–1435. Bibcode:2003MaMol..36.1433N. doi:10.1021/ma025792r.
3. Tamaki Nakano; Kazuyuki Takewaki; Tohru Yade; Yoshio Okamoto (2001). "Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts". J. Am. Chem. Soc. 123 (37): 9182–9183. doi:10.1021/ja0111131. PMID 11552835.

This article about a hydrocarbon is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Fluorenes
• Polycyclic aromatic hydrocarbons
• Vinylidene compounds
• Hydrocarbon stubs