12H-Dibenzo(B,H)floren-12-one

Base Information

• Chemical Name: 12H-Dibenzo(B,H)floren-12-one
• CAS No.: 53223-75-9
• Molecular Formula: C21H12O
• Molecular Weight: 280.326
• DSSTox Substance ID: DTXSID10201324
• Nikkaji Number: J612.364C
• Wikidata: Q83074513
• Mol file: 53223-75-9.mol

Synonyms:12H-DIBENZO(B,H)FLOREN-12-ONE;12H-Dibenzo[b,h]fluoren-12-one;53223-75-9;2,3,6,7-dibenzofluorene;SCHEMBL16144676;DTXSID10201324;JZNRMTLFMCNYBH-UHFFFAOYSA-N

Chemical Property of 12H-Dibenzo(B,H)floren-12-one

Chemical Property:

• Vapor Pressure: 5.98E-11mmHg at 25°C
• Boiling Point: 520.9°Cat760mmHg
• Flash Point: 233.8°C
• Density: 1.315g/cm³
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 280.088815002
• Heavy Atom Count: 22
• Complexity: 415

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C4=CC5=CC=CC=C5C=C4C3=O

Technology Process of 12H-Dibenzo(B,H)floren-12-one

There total 16 articles about 12H-Dibenzo(B,H)floren-12-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2,3-6,7-dibenzofluorene (242-47-7) → 12H-dibenzo[b,h]fluoren-12-one (53223-75-9)

Guidance literature:

With air; graphene-supported KOH composite; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1002/cplu.201300123

Reference yield: 47.0%

naphthocyclopentadienone (159113-90-3) + ortho-(phenylsulfonylmethyl)benzaldehyde (468751-38-4) → 12H-dibenzo[b,h]fluoren-12-one (53223-75-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃;

DOI:10.1055/s-2006-942468

Reference yield: 7.0%

tri(naphthalene-2-yl)methanol (216070-60-9) → 12-(naphthalen-2-yl)-12H-dibenzo[b,h]fluoren-12-ol (1422130-66-2) + 7-(naphthalen-2-yl)-7H-dibenzo[b,g]fluoren-7-ol (1422130-67-3) + 12H-dibenzo[b,h]fluoren-12-one (53223-75-9)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper(II) acetate monohydrate; In dodecane; at 170 ℃; for 8h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo4000465

upstream raw materials:

1,2-bis(dibromomethyl)benzene

naphthocyclopentadienone

(2-aminonaphthalen-3-yl)(naphthalen-3-yl)methanone

ortho-(phenylsulfonylmethyl)benzaldehyde

Downstream raw materials:

13H-dibenzo[a,h]fluoren-13-one

2,3-6,7-dibenzofluorene

Refernces

• 1、 Itoh, Masaki,Hirano, Koji,Satoh, Tetsuya,Shibata, Yu,Tanaka, Ken,Miura, Masahiro. "Rhodium- and iridium-catalyzed dehydrogenative cyclization through double C-H bond cleavages to produce fluorene derivatives". . p. 1365 - 1370. Retrieved 2013/03/28.
• 2、 Mala'Bi, Tahani,Pogodin, Sergey,Cohen, Shmuel,Agranat, Israel. "Reversible Friedel-Crafts acyl rearrangements of planar polycyclic aromatic ketones: Dibenzofluorenones". . p. 21797 - 21810. Retrieved 2013/11/06.