39654-52-9

Basic information

• Product Name: 10,11-DIBROMO-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE
• Synonyms: 10,11-DIBROMO-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE;TRANS-10,11-DIBROMODIBENZOSUBERONE
• CAS NO: 39654-52-9
• Molecular Formula: C₁₅H₁₀Br₂O
• Molecular Weight: 366.05
• Mol File: 39654-52-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 213 °C (dec.)(lit.)
• Boiling Point: 395.6°C at 760 mmHg
• Flash Point: 105.4°C
• Appearance: /
• Density: 1.751g/cm³
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 10,11-DIBROMO-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 10,11-DIBROMO-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE(39654-52-9)
• EPA Substance Registry System: 10,11-DIBROMO-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE(39654-52-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 39654-52-9(Hazardous Substances Data)

Usage

Uses

10,11-Dibromo10,11-dihydro-5-dibenzosuberenone is an intermediate in the synthesis of 10-Hydroxy (E)-Amitriptyline (D462790). (5E)-5-[3-(dimethylamino)propylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol is a metabolite of amitriptyline (A633350) which is a dibenzocycloheptadiene derivative and an antidepressant (1). Amitriptyline is also a TrkA and TrkB receptor agonist and exhibits neurotrophic and anti-inflammatory activities (2,3). Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA).

InChI:InChI=1/C15H10Br2O/c16-13-9-5-1-3-7-11(9)15(18)12-8-4-2-6-10(12)14(13)17/h1-8,13-14H

Upstream product

• 2222-33-5 dibenzosuberenon 
• 1210-35-1 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one 

Downstream Products

• 2222-33-5 dibenzosuberenon 
• 16171-52-1 10-(4-methyl-1-piperazinyl)-5H-dibenzocyclohepten-5-one 
• 658064-96-1 10-(2-methoxy-phenyl)-5H-dibenzo[a,d]cyclohepten-5-ol 
• 71192-56-8 10-phenyl-5H-dibenzo[a,d]cyclohepten-5-ol 
• 862554-89-0 10-bromo-5-(4-methoxyphenyl)-5H-dibenzo[a,d]cyclohepten-5-ol 

Relevant articles and documents

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Synthesis of 11,12-didehydrodibenzo[a,e]cycloocten-5(6H)-one: A strained eight-membered alkyne

An eight-step synthesis of 11,12-didehydrodibenzo[ a,e]cycloocten-5(6H)-one (10) was developed. The structure of 10 was assigned by spectroscopic means and confirmed by X-ray analysis of its 2,4-dinitrophenylhydrazone derivative. Reaction of the triple bond of 10 with dicarbonyl(h5-cyclopentadienyl)cobalt or dicarbonyl(η5-pentamethylcyclopentadienyl)cobalt gave the corresponding metal-stabilized cyclobutadiene complexes. Georg Thieme Verlag Stuttgart.

Polycyclic phosphiranes: Synthesis of C-substituted BABAR-Phos compounds

BABAR-Phos is a very stable polycyclic phosphirane which is easily synthesized in few steps from dibenzosuberenone. BABAR-Phos is remarkably stable and is not oxygenated with O2 nor does it react with sulfur in boiling toluene. BABAR-Phos can be used as a ligand in homogenous catalysis. Substituents at the carbon of the PC2 heterocycle can be introduced and asymmetric BABAR-Phos were prepared. The coordination chemistry of rhodium complexes containing these as ligands was investigated.