4964-71-0

Basic information

• Product Name: 5-Bromoquinoline
• Synonyms: Quinoline, 5-bromo-;5-Bromoquinoline 97%;5-BROMOQUINOLINE;RARECHEM AK ML 0010;5-Bromoquinoline,97%;5-bronoquinoline;5-bromooquinoline
• CAS NO: 4964-71-0
• Molecular Formula: C₉H₆BrN
• Molecular Weight: 208.05
• EINECS: -0
• Product Categories: Halides;Heterocycles;Quinoline;Quinoline Derivertives;Halogenated;Organohalides;Haloquinolines;Quinolines;Boronic Acid;Heterocyclic Compounds
• Mol File: 4964-71-0.mol

Chemical Properties

• Melting Point: 50-52°C
• Boiling Point: 105-107°C 1mm
• Flash Point: 105-107°C/1mm
• Appearance: Pale yellow liquid
• Density: 1.5617 (rough estimate)
• Vapor Pressure: 0.00261mmHg at 25°C
• Refractive Index: 1.6641 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.88±0.12(Predicted)
• BRN: 115148
• CAS DataBase Reference: 5-Bromoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoquinoline(4964-71-0)
• EPA Substance Registry System: 5-Bromoquinoline(4964-71-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4964-71-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C9H6BrN/c10-8-4-1-5-9-7(8)3-2-6-11-9/h1-6H

Upstream product

• 50358-42-4 6-amino-5-bromoquinoline 
• 56-81-5 glycerol 
• 591-19-5 m-Bromoaniline 
• 91-22-5 quinoline 
• 611-34-7 5-Aminoquinoline 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 333383-82-7 N-(3-bromo-phenyl)-N-(3-oxo-propyl)-methanesulfonamide 
• 333383-83-8 N-(3-bromo-phenyl)-4-methyl-N-(3-oxo-propyl)-benzenesulfonamide 
• 7510-48-7 N-(3-bromophenyl)-4-methyl-benzenesulfonamide 
• 83922-51-4 3-(methylsulfonyl)amino-1-bromo-benzene 
• 580-15-4 6-aminoquinoline 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 846038-45-7 5-bromoquinoline N-oxide 

Downstream Products

• 873409-48-4 5-phenoxyquinoline 
• 99465-09-5 5-bromohydroxyquinoline 
• 846038-45-7 5-bromoquinoline N-oxide 
• 176967-80-9 5-bromo-8-nitroquinoline 
• 855837-58-0 5-bromo-6-nitroquinoline 
• 127791-49-5 5,5'-biquinoline 
• 67532-97-2 5-trimethylsilylquinoline 
• 860717-85-7 [5]quinolyl-[8]quinolyl ether 
• 804430-48-6 5-bromo-quinoline-8-sulfonic acid 
• 1605-49-8 5-(piperidin-1-yl)quinoline 
• 63935-00-2 phenyl(quinolin-5-yl)amine 
• 37385-00-5 benzyl(quinolin-5-yl)amine 
• 355386-94-6 quinolin-5-ylboronic acid 
• 952406-60-9 tert-butyl (3S)-1-quinolin-5-ylpyrrolidin-3-ylcarbamate 

Relevant articles and documents

A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides

Deoxygenation of heteroaromatic N-oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N-oxide derivatives under mild conditions. A diverse range of mono- and bis N-oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N-oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring.

Composite taken as URAT 1 inhibitor

The invention provides a series of composite with a formula (I), wherein n is selected from 1, 2 or 3, X is selected from O or S, Q is selected from C or N, and R is selected from H, halogen or -C1-6.The composite can be used as the URAT 1 inhibitor and can be used for treating hyperuricemia and gout.

One-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide under microwave-assisted conditions

A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.

Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin.

3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors

New pyridazin-3(2H)-one derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the phosphodiesterase IV (PDE4).

CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS

This invention pertains to certain carbamic acid compounds of the following formula, which inhibit HDAC (histone deacetylase) activity wherein: A is independently an unsubstituted or substituted bicyclic C9-10heteroaryl group (e.g., quinolinyl; quinoxalinyl; benzoxazolyl; benzothiazolyl); Q is an acid leader group, and is independently an unsubstituted or substituted, saturated or unsaturated C1 7alkylene group having a backbone length of 4 or less; with the proviso that if A is unsubstituted benzothiazol-2-yl, then Q is an unsaturated group; and with the proviso that if A is unsubstituted quinolin-6-yl, then Q is unsubstituted at the α-position; and with the proviso that A is not benzimidazol-2-yl; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both invitro and in vivo, to inhibit HDAC, and in the treatment of conditions mediated by HDAC, cancer, proliferative conditions, psoriasis, etc.

Arylsulfonamide ethers, and methods of use thereof

Novel arylsulfonamide ether compounds and pharmaceutical compositions thereof are described. The use of the novel arylsulfonamide ether compounds and pharmaceutical compositions thereof as inhibitors of interleukin-1β converting enzyme and other cysteine proteases in the ICE family is also decribed. In addition, methods of treating stroke, inflammatory diseases, septic shock, repurfusion injury, Alzheimer's disease, and shigellosis using a compound of the invention or a pharmaceutical composition thereof are described.

Bromination of isoquinoline, quinoline, quinazoline and quinoxaline in strong acid

Bromination of benzazines and benzodiazines most often gives a mixture of products. In this paper, we show that isoquinoline (1) may be regioselectively monobrominated in concentrated H2SO4 using NBS or in CF3SO3H using N,N′-dibromoisocyanuric acid (DBI) to give 5-bromoisoquinoline (2). The bromination was found to be highly sensitive to the choice of brominating agent, acid, temperature and concentration. Quinoline, quinazoline and quinoxaline may be brominated likewise, although with the strong regioselectivity reserved to isoquinoline.

Synthesis of a fluorine-18-labelled derivative of 6-nitroquipazine, as a radioligand for the in vivo serotonin transporter imaging with PET.

Considerable efforts have been engaged in the design, synthesis and pharmacological characterization of radioligands for imaging the serotonin transporter, based on its implication in several neuropsychiatric diseases, such as depression, anxiety and schizophrenia. In the 5-halo-6-nitroquipazine series, the fluoro derivative has been designed for positron emission tomography (PET). The corresponding 5-iodo-, 5-bromo- and 5-chloro N-Boc-protected quipazines as labelling precursors, as well as 5-fluoro-6-nitroquipazine as a reference compound have been synthesized. 5-[(18)F]Fluoro-6-nitroquipazine has been radiolabelled with fluorine-18 (positron-emitting isotope, 109.8 min half-life) by nucleophilic aromatic substitution from the corresponding N-Boc protected 5-bromo- and 5-chloro-precursors using K[(18)F]F-K(222) complex in DMSO by conventional heating (145 degrees C, 2 min) or microwave activation (50 W, 30-45 s), followed by removal of the protective group with TFA. Typically, 15-25 mCi (5.5-9.2 GBq) of 5-[(18)F]fluoro-6-nitroquipazine (1-2 Ci/micromol or 37-72 GBq/micromol) could be obtained in 70-80 min starting from a 550-650 mCi (20.3-24.0 GBq) aliquot of a cyclotron [(18)F]F(-) production batch (2.7-3.8% non decay-corrected yield based on the starting [(18)F]fluoride). Ex vivo studies (biodistribution in rat), as well as PET imaging (in monkey) demonstrated that 5-[(18)F]fluoro-6-nitroquipazine ([(18)F]-1d) readily crossed the blood brain barrier and accumulated in the regions rich in 5-HT transporter (frontal- and posterial cortex, striata). However, the low accumulation of the tracer in the thalamus (rat and monkey) as well as the comparable displacement of the tracer observed with both citalopram, a -HT re-uptake inhibitor and maprotiline, a norepinephrine re-uptake inhibitor (rat), indicate that 5-[(18)F]fluoro-6-nitroquipazine ([(18)F]-1d) does not have the suggested potential for PET imaging of the serotin transporter (SERT).

THROMBIN INHIBITORS

Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions and are selected from the group consisting of: or a pharmaceutically acceptable salt thereof, wherein T is selected from the group consisting of D, E, F, G, H, I, and J are independently N or CY 1, provided that the number of such variables D, E, F, G, H, I, and J representing N is 0, 1, or 2; K, L, M and Q are independently NH or CY1Y2, provided that the number of such variables D, E, F, K, L, M, and Q representing N is 0, 1, or 2; Y1 and Y2 are independently selected from the group consisting of hydrogen, C1-4 alkyl, halogen, anino, or hydroxy; A is