2,2'-Dibromo-1,1'-binaphthyl - 74866-28-7

2,2'-Dibromo-1,1'-binaphthyl

Catalog Number: EVT-461876
CAS Number: 74866-28-7
Molecular Formula: C20H12Br2
Molecular Weight: 412.1 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
2,2'-Dibromo-1,1'-binaphthyl (DBBN) is a chiral compound that has gained significant attention in various fields of research due to its unique chemical structure and biological activity. DBBN is a member of the binaphthyl family, which is known for its diverse applications in organic synthesis, catalysis, and medicinal chemistry.
Applications in Various Fields
2,2'-Dibromo-1,1'-binaphthyl has various applications in medical research, including its role in drug development and clinical trials. 2,2'-Dibromo-1,1'-binaphthyl has been shown to have potential as a chemotherapeutic agent for the treatment of cancer. It has also been investigated as a potential treatment for viral infections, including hepatitis C and herpes simplex virus. In environmental research, 2,2'-Dibromo-1,1'-binaphthyl has been shown to have effects on ecosystems and can be used in pollution management. In industrial research, 2,2'-Dibromo-1,1'-binaphthyl can be used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account when using 2,2'-Dibromo-1,1'-binaphthyl in industrial applications.

Properties

CAS Number

74866-28-7

Product Name

2,2'-Dibromo-1,1'-binaphthyl

IUPAC Name

2-bromo-1-(2-bromonaphthalen-1-yl)naphthalene

Molecular Formula

C20H12Br2

Molecular Weight

412.1 g/mol

InChI

InChI=1S/C20H12Br2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H

InChI Key

IJUDEFZBMMRSNM-UHFFFAOYSA-N

SMILES

C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)Br)Br

Canonical SMILES

C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)Br)Br
Method of Synthesis or Extraction
2,2'-Dibromo-1,1'-binaphthyl can be synthesized using various methods, including the Suzuki-Miyaura coupling reaction, the Stille coupling reaction, and the Negishi coupling reaction. The Suzuki-Miyaura coupling reaction is the most commonly used method for the synthesis of 2,2'-Dibromo-1,1'-binaphthyl. This method involves the reaction of 2-bromo-1-naphthylboronic acid with 2-bromo-1-naphthalene in the presence of a palladium catalyst and a base. The efficiency and yield of this method are high, with a yield of up to 90%. However, this method requires the use of toxic solvents and reagents, which can have adverse environmental and safety considerations.
Chemical Structure and Biological Activity
2,2'-Dibromo-1,1'-binaphthyl has a unique chemical structure that consists of two naphthalene rings connected by a central binaphthyl unit. This structure imparts 2,2'-Dibromo-1,1'-binaphthyl with chiral properties, making it an important compound in asymmetric synthesis and chiral separation. 2,2'-Dibromo-1,1'-binaphthyl has been shown to exhibit various biological activities, including antitumor, antiviral, and antibacterial activities. The mechanism of action of 2,2'-Dibromo-1,1'-binaphthyl involves the inhibition of cell proliferation and the induction of apoptosis in cancer cells. 2,2'-Dibromo-1,1'-binaphthyl has also been shown to inhibit the replication of the hepatitis C virus and the herpes simplex virus.
Biological Effects
2,2'-Dibromo-1,1'-binaphthyl has been shown to have significant effects on cell function and signal transduction. It has been shown to inhibit the activity of various enzymes, including protein kinase C and phospholipase A2. 2,2'-Dibromo-1,1'-binaphthyl has also been shown to modulate the activity of ion channels, including the voltage-gated potassium channel. 2,2'-Dibromo-1,1'-binaphthyl has potential therapeutic effects in the treatment of cancer, viral infections, and inflammatory diseases. However, it also has potential toxic effects, including hepatotoxicity and neurotoxicity.
Future Perspectives and Challenges
The use of 2,2'-Dibromo-1,1'-binaphthyl in scientific research is limited by its potential toxicity and the lack of understanding of its mechanism of action. Future research should focus on elucidating the mechanism of action of 2,2'-Dibromo-1,1'-binaphthyl and identifying its potential therapeutic targets. Additionally, efforts should be made to develop safer and more efficient methods for the synthesis of 2,2'-Dibromo-1,1'-binaphthyl. The potential applications of 2,2'-Dibromo-1,1'-binaphthyl in various fields of research make it an important compound for future research.

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