83-53-4 Usage
Description
1,4-Dibromonaphthalene is a light orange-beige fine crystalline powder that is primarily used as a pharmaceutical intermediate. It is synthesized from naphthalene or 1-bromonaphthalene and serves as a starting material for the preparation of various compounds.
Uses
Used in Pharmaceutical Industry:
1,4-Dibromonaphthalene is used as a pharmaceutical intermediate for the synthesis of novel, orally active dual NK1/NK2 antagonists. These antagonists have potential applications in treating various conditions, such as anxiety, depression, and other disorders related to the neurokinin receptor system.
Used in Chemical Synthesis:
1,4-Dibromonaphthalene is used as a starting material for the synthesis of tribromo methoxynaphthalenes, which are compounds with potential applications in various chemical and industrial processes.
Additionally, 1,4-dibromonaphthalene is used in the preparation of 5,8-dibromo-1,4-naphthoquinone and 5,8-diiodo-1,4-naphthoquinone, which are important intermediates in the synthesis of various organic compounds and may have potential applications in the development of new pharmaceuticals and other chemical products.
Used in Annelation of PAHs:
1,4-Dibromonaphthalene is also used in the annelation of polycyclic aromatic hydrocarbons (PAHs), which are a class of compounds with potential applications in various fields, such as materials science, organic synthesis, and pharmaceuticals. The annelation process involves the formation of additional rings in the PAH structure, leading to the creation of more complex and functionalized molecules.
Preparation
An environment-friendly method was developed to synthesize 1,4-dibromonaphthalene (1,4-DBN) using 1,3-dialkylimidazolium and pyridinium ionic liquids as catalysts, over which the yields of 1,4-DBN were obtained as high as 100%.An environment-friendly method for synthesis of 1,4-dibromo-naphthalene in aqueous solution of ionic liquids
Check Digit Verification of cas no
The CAS Registry Mumber 83-53-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 83-53:
(4*8)+(3*3)+(2*5)+(1*3)=54
54 % 10 = 4
So 83-53-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H6Br2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
83-53-4Relevant articles and documents
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Bayer,O'Reilly
, p. 311 (1958)
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Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 1621 - 1629 (2020/02/04)
A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
PROCESS FOR PRODUCING 1,5-DIBROMONAPHTHALENE
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Paragraph 0032-0049, (2018/03/23)
PROBLEM TO BE SOLVED: To provide a process for producing 1,5-dibromonaphthalene that can efficiently produce 1,5-dibromonaphthalene. SOLUTION: 1,5-dibromonaphthalene is produced by a process for producing 1,5-dibromonaphthalene having a bromination step of reacting at least one of naphthalene and 1-bromonaphthalene with bromine in the presence of a porous material. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT