101870-60-4

Basic information

• Product Name: 3-BROMO-2-CHLOROQUINOLINE
• Synonyms: 3-BROMO-2-CHLOROQUINOLINE
• CAS NO: 101870-60-4
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.5
• Mol File: 101870-60-4.mol

Chemical Properties

• Melting Point: 96-98 °C
• Boiling Point: 311.2 °C at 760 mmHg
• Flash Point: 142 °C
• Appearance: /
• Density: 1.673 g/cm³
• Vapor Pressure: 0.00105mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -2.14±0.50(Predicted)
• CAS DataBase Reference: 3-BROMO-2-CHLOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-CHLOROQUINOLINE(101870-60-4)
• EPA Substance Registry System: 3-BROMO-2-CHLOROQUINOLINE(101870-60-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 101870-60-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-2-chloroquinoline is utilized as a key intermediate in the synthesis of various pharmaceuticals due to its antiviral, antimicrobial, and anti-tumor activities. Its unique structure allows for the development of new drugs targeting a range of health conditions.
Used in Organic Synthesis:
In the realm of organic synthesis, 3-bromo-2-chloroquinoline serves as a valuable reagent, contributing to the creation of complex organic compounds for research and commercial applications.
Used in Chemical Research:
3-Bromo-2-chloroquinoline is also employed in chemical research, where its properties and reactions are studied to gain insights into the behavior of similar compounds and to advance the understanding of organic chemistry.

InChI:InChI=1/C9H5BrClN/c10-7-5-6-3-1-2-4-8(6)12-9(7)11/h1-5H

Upstream product

• 22615-00-5 3-bromoquinoline N-oxide 
• 939-16-2 3-bromoquinolin-2-one 
• 5332-24-1 3-bromoquinoline 

Downstream Products

• 941-91-3 3-bromo-1-methylquinolin-2(1H)-one 
• 114414-78-7 neocryptolepine 
• 898559-23-4 3-bromo-2-iodoquinoline 
• 222317-29-5 3-bromo-2-methoxyquinoline 
• 243-38-9 6H-quinindoline 

Relevant articles and documents

Hetarynic synthesis and chemical transformations of dihydrodiquinolinopyrazines

New dihydrodiquinolinopyrazines (DHDQP) were easily obtained by hetarynic dimerization of 2-alkylamino-3-bromoquinolines in the presence of complex base NaNH2-t-BuONa. Functionalization and derivatization of these new heterocycles are described.

A novel and efficient synthesis of 2,3-dichloroquinoline

2,3-Dichloroquinoline was prepared in three steps in good overall yield from commercial 3-bromoquinoline via N-oxide formation and rearrangement to 3-bromocarbostyril, followed by a one-pot conversion to 3-bromo-2- chloroquinoline and halogen exchange to the title compound.

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

New synthetic approaches towards analogues of bedaquiline

Multi-drug resistant tuberculosis (MDR-TB) is of growing global concern and threatens to undermine increasing efforts to control the worldwide spread of tuberculosis (TB). Bedaquiline has recently emerged as a new drug developed to specifically treat MDR-

A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions

The indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3), and isoneocryptolepine (4) are important tools in traditional medicine. Now, their precursors 1a-4a were synthesized in two steps starting from the corresponding bromo-iodoquinolines. Our strategy is based on palladium-catalyzed reactions, applying regioselective Buchwald-Hartwig amination on 2,3- and 3,4-dihaloquinolines followed by an intramolecular Heck-type reaction. Both steps were carried out under microwave irradiation.

Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide

Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.

Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: Application in (Z)-dibromoalkene syntheses

(Chemical Equation Presented) Tetrabutylammonlum trlbromlde (TBATB) has been found to be a unique bromodeboronatlon reagent for organotrlf luoroborates. When compared to previously reported bromodeboronatlon methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High reglo- and chemoselectlvlty are observed In the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dlbromoalkenes from terminal alkynes has been developed using the TBATB-medlated bromodeboronatlon as a key step.

REACTIONS OF 3-SUBSTITUTED QUINOLINE 1-OXIDES WITH ACYLATING AGENTS

Reactions of 3-fluoro- (1a), 3-bromo- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table).While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxyquinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.