20151-40-0

Basic information

• Product Name: 2,4-DIBROMOQUINOLINE
• Synonyms: 2,4-DIBROMOQUINOLINE;2,4-DibroMoquinoline 97%
• CAS NO: 20151-40-0
• Molecular Formula: C₉H₅Br₂N
• Molecular Weight: 286.9507
• Mol File: 20151-40-0.mol

Chemical Properties

• Melting Point: 92-94 ºC
• Boiling Point: 344.3 °C at 760 mmHg
• Flash Point: 162 °C
• Appearance: /
• Density: 1.923 g/cm³
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.12±0.50(Predicted)
• CAS DataBase Reference: 2,4-DIBROMOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIBROMOQUINOLINE(20151-40-0)
• EPA Substance Registry System: 2,4-DIBROMOQUINOLINE(20151-40-0)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41
• Safety Statements: 26-39-45
• RIDADR: UN 2811
• WGK Germany: 3
• Hazardous Substances Data: 20151-40-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4-Dibromoquinoline is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
2,4-Dibromoquinoline is used as a key component in the development of new drugs. Its chemical properties enable it to interact with biological targets, such as enzymes and receptors, which can lead to the discovery of novel therapeutic agents with potential applications in the treatment of various diseases.
Used in Agrochemical Industry:
2,4-Dibromoquinoline is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to form stable compounds with other chemical groups makes it a valuable resource in the development of effective crop protection products.
Used in Research and Development:
2,4-Dibromoquinoline is used as a research tool in academic and industrial laboratories. Its reactivity and structural features make it an interesting subject for studying various chemical reactions and exploring new synthetic pathways.

InChI:InChI=1/C9H5Br2N/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5H

Upstream product

• 70254-44-3 2,4-dihydroxyquinoline 
• 20146-63-8 2-bromo-4-nitroquinoline 
• 56-57-5 4-nitroquinoline-N-oxide 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 141-82-2 malonic acid 
• 62-53-3 aniline 
• 141-78-6 ethyl acetate 
• 22614-98-8 4-bromoquinoline-N-oxide 
• 67-66-3 chloroform 
• 10025-87-3 trichlorophosphate 
• 7789-60-8 phosphorus tribromide 

Downstream Products

• 64658-05-5 2-bromo‐4‐chloroquinoline 
• 938-39-6 4-bromo-2-hydroxyquinoline 
• 703-61-7 2,4-dichloroquinoline 
• 532392-87-3 2,4-dibromoquinoline-3-carbaldehyde 
• 857206-12-3 2-bromo-4-phenylquinoline 
• 36825-35-1 2-bromoquinolin-4-ylamine 
• 1000007-11-3 2-bromo-4-phenylsulfanyl-quinoline 
• 95104-24-8 2-bromoquinoline-4-carbonitrile 
• 104997-49-1 ethyl 2-bromoquinoline-4-carboxylate 
• 18706-25-7 4-bromo-2-(trifluoromethyl)quinoline 

Relevant articles and documents

Novel coumarin- and quinolinone-based polycycles as cell division cycle 25-A and -C phosphatases inhibitors induce proliferation arrest and apoptosis in cancer cells

Cell division cycle phosphatases CDC25 A, B and C are involved in modulating cell cycle processes and are found overexpressed in a large panel of cancer typology. Here, we describe the development of two novel quinone-polycycle series of CDC25A and C inhi

Coumarin derivative and analogue, preparation method and application thereof

The invention relates to a coumarin derivative and analogue, a preparation method and application thereof, belongs to the field of chemical medicines, and provides a compound shown as a formula I or apharmaceutically acceptable salt thereof, and a preparation method and application of the compound. According to the invention, biological experiments show that the compound has a strong in-vitro anti-fibrosis effect, can obviously reduce deposition of intercellular collagenous fibers on TGF-beta induced NRK-49F cells, and has inhibition on migration of HUVEC cells; and the compound with the structure has a certain curative effect on carbon tetrachloride induced hepatic fibrosis and bleomycin induced pulmonary fibrosis mouse models, is relatively low in toxicity, and provides a new choice forclinical treatment of tissue fibrosis diseases including hepatic fibrosis, pulmonary fibrosis and renal fibrosis.

Methoxyl regulation-based wide-band yellow phosphorescent 2-phenylquinoline iridium (III) complex and preparation method and application thereof

The invention discloses a methoxy regulation-based wide-band yellow phosphorescent 2-phenylquinoline iridium (III) complex and a preparation method and application thereof. The structural formula of the complex is shown in the specification, wherein R1 an

Design, synthesis and discovery of 2(1H)-quinolone derivatives for the treatment of pulmonary fibrosis through inhibition of TGF-β/smad dependent and independent pathway

Idiopathic pulmonary fibrosis (IPF) is a progressive, life-threatening and interstitial lung disease with the median survival of only 3–5 years. However, due to the unclear etiology and problems in accurate diagnosis, up to now only two drugs were approved by FDA for the treatment of IPF and their outcome responses are limited. Numerous studies have shown that TGF-β is the most important cytokine in the development of pulmonary fibrosis and plays a role through its downstream signaling molecule TGF-binding receptor Smads protein. In this paper, compounds bearing 2(1H)-quinolone scaffold were designed and their anti-fibrosis effects were evaluated. Of these compounds, 20f was identified as the most active one and could inhibit TGF-β-induced collagen deposition of NRK-49F cells and mouse fibroblasts migration with comparable activity and lower cytotoxicity than nintedanib in vitro. Further mechanism studies indicated that 20f reduced the expression of fibrogenic phenotypic protein α-SMA and collagen Ⅰ by inhibiting the TGF-β/Smad dependent pathways and ERK1/2 and p38 pathways. Moreover, compared with the nintedanib, 20f (100 mg/kg/day, p.o) more effectively alleviated collagen deposition in lung tissue and delayed the destruction of lung tissue structure both in bleomycin-induced prevention and treatment mice pulmonary fibrosis models. The immunohistochemical experiments further showed that 20f could block the expression level of phosphorylated Smad3 in the lung tissue cells, which resulted in its anti-fibrosis effects in vivo. In addition, 20f demonstrated good bioavailability (F = 41.55% vs 12%, compare with nintedanib) and an appropriate elimination half-life (T1/2 = 3.5 h), suggesting that 20f may be a potential drug candidate for the treatment of pulmonary fibrosis.

Synthesis of 4,5-bis(dimethylamino)quinolines and the dual direction of their protonation

A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.

Multiple regioselective functionalizations of quinolines via magnesiations

A wide range of polyfunctionalized quinolines was prepared via chemo- and regioselective magnesiation reactions using appropriate Mg reagents, such as i-PrMgCl-LiCl, MesMgBr·LiCl, Mes2Mg·2LiBr, TMPMgCl·LiCl, and TMP2Mg·2LiCl. An application to the total synthesis of the biologically active compound talnetant was performed (six steps, 28%).

Spiro-cyclic beta-amino acid derivatives as inhibitors of matrix metalloproteases and TNF-alpha converting enzyme (TACE)

The present application describes novel spiro-cyclic β-amino acid derivatives of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 3-13 membered carbocycle or heterocycle, ring C forms a 3-11 membered spiro-carbocycle or spiro-heterocycleon ring B, and the other variables are defined in the present specification, which are useful as as matrix metalloproteinases (MMP), TNF-α converting enzyme (TACE), and/or aggrecanase inhibitors.

Cyclic hydroxamic acids as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE)

The present application describes novel cyclic hydroxamic acids of formula I: or pharmaceutically acceptable salt forms thereof, wherein ring B is a 5-7 membered cyclic system containing from 0-2 heteroatoms selected from O, N, NR1, and S(O)p, and 0-1 carbonyl groups and the other variables are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-α converting enzyme (TACE), aggrecanase or a combination thereof, pharmaceutical compositions containing the same, and methods of using the same.

Acetylene Chemistry. Part 27. Palladium Catalysed C-C Bond Formation Between Quinoline and Mono-substituted Alkynes: Synthesis of 4-Alkynyl-2-bromoquinolines

Six new 4-alkynyl-2-bromoquinolines have been synthesised via palladium catalysed C-C bond formation between 2,4-dibromoquinoline and mono-substituted alkynes.Position of the alkyne substituent was confirmed to be at C-4 by an nOe experiment on some methoxy derivatives prepared by nucleophilic displacement of bromo substituent.

2,4-Dihalogenoquinolines. Synthesis, Orientation Effects and 1H and 13C NMR Spectral Studies

Isomer ratios for the syntheses of 2,4-dichloroquinolines from meta-substituted and 3,4-disubstituted anilines are reported, a synthesis of 2,4-dibromoquinoline 1b is also described.The structures of certain bromination products 17 and 1f obtained from 4-hydroxy-2-quinolone have been revised.A thorough study of the 1H and 13C NMR spectra of a series of 2,4-dihalogenoquinolines is presented and the effects of the halogen substituents on JCH couplings are highlighted.