9,9-Dibromo-9H-fluorene

Base Information

• Chemical Name: 9,9-Dibromo-9H-fluorene
• CAS No.: 15300-75-1
• Molecular Formula: C13H8Br2
• Molecular Weight: 324.015
• Hs Code.: 2903999090
• DSSTox Substance ID: DTXSID00496545
• Nikkaji Number: J81.844E
• Wikidata: Q82345493
• Mol file: 15300-75-1.mol

Synonyms:9,9-DIBROMO-9H-FLUORENE;9,9-dibromofluorene;15300-75-1;SCHEMBL3363644;DTXSID00496545

Chemical Property of 9,9-Dibromo-9H-fluorene

Chemical Property:

• Melting Point: 114 °C(Solv: acetone (67-64-1))
• Boiling Point: 342.2±42.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.846±0.06 g/cm3(Predicted)
• LogP: 4.65790
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 323.89723
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3C2(Br)Br

Technology Process of 9,9-Dibromo-9H-fluorene

There total 9 articles about 9,9-Dibromo-9H-fluorene 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: 41.0%

9-diazofluorenone (832-80-4) → 9,9-dibromo-9H-fluorene (15300-75-1)

Guidance literature:

With bromine; In diethyl ether; for 0.5h; Ambient temperature;

Reference yield: 8.0%

9H-fluorene (86-73-7) + sodium acetate (127-09-3) → 9,9-dibromo-9H-fluorene (15300-75-1) + 9-acetoxy-9H-fluorene (25017-68-9)

Guidance literature:

With dipotassium peroxodisulfate; lithium bromide; In acetic acid; at 113 ℃; for 6h;

DOI:10.1021/jo00231a017

Reference yield:

9H-fluorene (86-73-7) → 9,9-dibromo-9H-fluorene (15300-75-1)

Guidance literature:

With tetrachloromethane; bromine; Irradiation_.Einwirkung von UV-Licht;

DOI:10.1021/ja01185a522

upstream raw materials:

9H-fluorene

9H-fluoren-9-yl bromide

9-diazofluorenone

sodium acetate

Downstream raw materials:

9,9-dimethyl-9H-fluorene

Benzhydrylidene-(9-bromo-9H-fluoren-9-yl)-amine

2-fluoren-9-ylidene-malononitrile

C₂₆H₁₇N

Refernces

CARBENOID REACTION: THE REACTION OF DIBROMODIPHENYLMETHANE, 9,9-DIBROMOFLUORENE AND 9,9-DICHLORO-9H-TRIBENZO[a.c.e]CYCLOHEPTENE WITH ALKYLLITHIUM IN THE PRESENCE OF OLEFINS

10.1016/0040-4020(67)80009-7

The study investigates the carbenoid reaction of various compounds with alkyllithium in the presence of olefins. Dibromodiphenylmethane reacts with methyllithium in the presence of ethyl vinyl ether to produce 1,1-diphenyl-2-ethoxycyclopropane and tetraphenylethylene. However, 9,9-dibromofluorene and 9,9-dichloro-9H-tribenzo[a.c.e]cycloheptene do not yield cyclopropane derivatives under similar conditions but instead produce compounds like 9,9'-bifluorenylidene and 9-methylene-9H-tribenzo[a.c.e]cycloheptene. The study explores the mechanisms behind these reactions, suggesting that the formation of cyclopropane derivatives is influenced by the stability of intermediates and the steric hindrance around the reaction centers. The results indicate that the reactivity of these compounds with olefins cannot be fully explained by existing hypotheses and may involve different transition states and intermediates.