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130-16-5,MFCD00006788
Catalog No.:AA000TRZ

130-16-5 | 5-Chloro-8-hydroxyquinoline

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Purity
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5g
98%
in stock  
$6.00   $4.00
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25g
98%
in stock  
$7.00   $5.00
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100g
98%
in stock  
$22.00   $15.00
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500g
98%
in stock  
$85.00   $60.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA000TRZ
Chemical Name:
5-Chloro-8-hydroxyquinoline
CAS Number:
130-16-5
Molecular Formula:
C9H6ClNO
Molecular Weight:
179.6030
MDL Number:
MFCD00006788
SMILES:
Clc1ccc(c2c1cccn2)O
Properties
Properties
 
BP:
348.7 °C at 760 mmHg  
Form:
Solid  
MP:
122-124 °C  
Refractive Index:
1.5330 (estimate)  
Solubility:
0.019g/l (experimental)  
Stability:
Light Sensitive  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
165  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
2.9  

Upstream Synthesis Route

[1]TetrahedronLetters,2015,vol.56,#46,p.6436-6439

[1]SyntheticCommunications,2009,vol.39,#9,p.1534-1548

[2]JournalofOrganicChemistry,2005,vol.70,#21,p.8590-8593

[1]ChemicalScience,2018,vol.9,#7,p.1782-1788

[2]JournaloftheIndianChemicalSociety,1945,vol.22,p.171

[1]Patent:CN108191753,2018,A,.Locationinpatent:Paragraph0040;0041;0049;0051;0053;0055

[1]TetrahedronLetters,1996,vol.37,#37,p.6695-6698

Downstream Synthesis Route

[1]ChemicalScience,2018,vol.9,p.1782-1788

[2]JournaloftheIndianChemicalSociety,1945,vol.22,p.171

[1]Bhat,Shridhar;Shim,JoongSup;Zhang,Feiran;Chong,CurtisRobert;Liu,JunO.[OrganicandBiomolecularChemistry,2012,vol.10,#15,p.2979-2992]

[2]Helgren,TravisR.;Chen,Congling;Wangtrakuldee,Phumvadee;Edwards,ThomasE.;Staker,BartL.;Abendroth,Jan;Sankaran,Banumathi;Housley,NicoleA.;Myler,PeterJ.;Audia,JonathonP.;Horn,JamesR.;Hagen,TimothyJ.[BioorganicandMedicinalChemistry,2017,vol.25,#3,p.813-824]

[3]Wangtrakuldee,Phumvadee;Byrd,MatthewS.;Campos,CristineG.;Henderson,MichaelW.;Zhang,Zheng;Clare,Michael;Masoudi,Ali;Myler,PeterJ.;Horn,JamesR.;Cotter,PeggyA.;Hagen,TimothyJ.[ACSMedicinalChemistryLetters,2013,vol.4,#8,p.699-703]

[4]Fu,Hai-Gen;Li,Zhi-Wen;Hu,Xin-Xin;Si,Shu-Yi;You,Xue-Fu;Tang,Sheng;Wang,Yan-Xiang;Song,Dan-Qing[Molecules,2019,vol.24,#3]

[5]Burckhalteretal.[JournaloftheAmericanChemicalSociety,1954,vol.76,p.4902,4905]

5799-68-8    130-16-5   
methanedisulfonicacidbis-(5-chloro-8quinolylester) 

[1]Ringier[HelveticaChimicaActa,1944,vol.27,p.1790,1793]

[1]Lengyel,Miklós;Erdélyi,Ferenc;Pergel,Enikö;Bálint-Polonka,Ágnes;Dobolyi,Alice;Bozsaki,Péter;Dux,Mária;Király,Kornél;Hegedüs,Tamás;Czirják,Gábor;Mátyus,Péter;Enyedi,Péter[MolecularPharmacology,2019,vol.95,#6,p.652-660]

[2]Bosshard[HelveticaChimicaActa,1944,vol.27,p.1736,1745]

[1]Jianbo,He;Tingting,Zhou;Yongjing,Cao;Yuanyuan,Zhang;Weiqing,Yang;Menglin,Ma[JournalofFluorescence,2018,vol.28,#5,p.1121-1126]

[2]CurrentPatentAssignee:HONEYWELLINTERNATIONALINC-DE767098,1939,C[DRP/DRBPOrg.Chem.][DRP/DRBPOrg.Chem.]

Literature

Title: Fragment-based discovery of 8-hydroxyquinoline inhibitors of the HIV-1 integrase-lens epithelium-derived growth factor/p75 (IN-LEDGF/p75) interaction.

Journal: Journal of medicinal chemistry 20130328

Title: Synthesis and characterization of 8-hydroxyquinoline complexes of tin(IV) and their application in organic light emitting diode.

Journal: Journal of fluorescence 20120901

Title: Novel structurally related compounds reactivate latent HIV-1 in a bcl-2-transduced primary CD4+ T cell model without inducing global T cell activation.

Journal: The Journal of antimicrobial chemotherapy 20120201

Title: Investigation on the pharmacological profile of antimony(III) complexes with hydroxyquinoline derivatives: anti-trypanosomal activity and cytotoxicity against human leukemia cell lines.

Journal: Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine 20110801

Title: Supramolecular synthon pattern in solid clioquinol and cloxiquine (APIs of antibacterial, antifungal, antiaging and antituberculosis drugs) studied by ³⁵Cl NQR, ¹H-¹⁷O and ¹H-¹⁴N NQDR and DFT/QTAIM.

Journal: Journal of molecular modeling 20110701

Title: Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

Journal: Journal of medicinal chemistry 20110127

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Grafting aluminum(III) 8-hydroxyquinoline derivatives on MCM-41 mesoporous silica for tuning of the light emitting color.

Journal: Journal of colloid and interface science 20100615

Title: 5-Chloro-8-hydroxy-quinolinium nitrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: Vibrational spectroscopic investigations, ab initio and DFT studies on 7-bromo-5-chloro-8-hydroxyquinoline.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20090501

Title: Bis(μ-5-chloro-quinolin-8-olato)-κN,O:O;κO:N,O-bis-[(acetato-κO,O')lead(II)].

Journal: Acta crystallographica. Section E, Structure reports online 20090301

Title: Outlook on Thailand's genomics and computational biology research and development.

Journal: PLoS computational biology 20080701

Title: Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands.

Journal: The Biochemical journal 20071101

Title: In vitro activities of cloxyquin (5-chloroquinolin-8-ol) against Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 20070301

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: The evaluation of liposome-water partitioning of 8-hydroxyquinolines and their copper complexes.

Journal: Environmental science & technology 20060315

Title: Latosińska JN, et al. Supramolecular synthon pattern in solid clioquinol and cloxiquine (APIs of antibacterial, antifungal, antiaging and antituberculosis drugs) studied by 35Cl NQR, 1H-17O and 1H-14N NQDR and DFT/QTAIM. J Mol Model. 2011 Jul;17(7):1781-800.

Title: Zhang W, et, al. Cloxiquine, a traditional antituberculosis agent, suppresses the growth and metastasis of melanoma cells through activation of PPARγ. Cell Death Dis. 2019 May 28;10(6):404.

Title: Hongmanee P, et, al. In vitro activities of cloxyquin (5-chloroquinolin-8-ol) against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2007 Mar;51(3):1105-6.

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