6-Bromo-2,3-dihydroquinolin-4(1H)-one

Base Information

• Chemical Name: 6-Bromo-2,3-dihydroquinolin-4(1H)-one
• CAS No.: 76228-06-3
• Molecular Formula: C9H8BrNO
• Molecular Weight: 226.073
• Hs Code.: 2933499090
• European Community (EC) Number: 867-558-2
• DSSTox Substance ID: DTXSID50353957
• Nikkaji Number: J2.953.012B
• Wikidata: Q82131840
• Mol file: 76228-06-3.mol

Synonyms:6-BROMO-2,3-DIHYDROQUINOLIN-4(1H)-ONE;76228-06-3;6-Bromo-2,3-dihydro-1H-quinolin-4-one;6-bromo-1,2,3,4-tetrahydroquinolin-4-one;MFCD00600620;Oprea1_166254;Oprea1_265034;4(1H)-QUINOLINONE, 6-BROMO-2,3-DIHYDRO-;SCHEMBL3015932;DTXSID50353957;WAFBCQPOMZIGTJ-UHFFFAOYSA-N;AMY38399;AKOS015834555;AB06523;CS-W018961;FS-2817;SY107822;6-bromo-4-oxo-1,2,3,4-tetrahydroquinoline;FT-0648707;EN300-126730;A847211;SR-01000389551;SR-01000389551-1;Z1269182177

Chemical Property of 6-Bromo-2,3-dihydroquinolin-4(1H)-one

Chemical Property:

• Melting Point: 225-228 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• Boiling Point: 359.1 °C at 760 mmHg
• PKA: 1.72±0.20(Predicted)
• Flash Point: 171 °C
• PSA: 29.10000
• Density: 1.559 g/cm³
• LogP: 2.58540
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 224.97893
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

6-Bromo-2,3-dihydroquinolin-4(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC2=C(C1=O)C=C(C=C2)Br

Technology Process of 6-Bromo-2,3-dihydroquinolin-4(1H)-one

There total 13 articles about 6-Bromo-2,3-dihydroquinolin-4(1H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

N-(4-bromophenyl)azetidin-2-one (7661-25-8) → 6-bromo-2,3-dihydro-4(1H)-quinolinone (76228-06-3)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 18 ℃; for 1h; Inert atmosphere;

DOI:10.1071/CH10465

Reference yield: 86.0%

2,3-dihydroquinolin-4(1H)-one (4295-36-7) → 6-bromo-2,3-dihydro-4(1H)-quinolinone (76228-06-3)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/jm5010539

Reference yield: 80.0%

N-[4-bromo-2-(3-hydroxy-prop-1-ynyl)-phenyl]-4-methyl-benzenesulfonamide → 6-bromo-2,3-dihydro-4(1H)-quinolinone (76228-06-3)

Guidance literature:

With trifluorormethanesulfonic acid; α,α,α-trifluorotoluene; for 8h; Reflux;

DOI:10.1080/00397911.2016.1196293

upstream raw materials:

N-(4-bromo-phenyl)-N-(toluene-4-sulfonyl)-β-alanine

N-(4-bromophenyl)azetidin-2-one

ethyl 3-(4-bromophenylamino)propanoate

4-bromo-aniline

Downstream raw materials:

C₁₀H₁₁BrN₄S

Refernces

• 1、 Sun, Guofeng,Cheng, Fengkai,Tao, Ruiheng,Sun, Yuxing,Pan, Jinpeng,Zhu, Yaohua,Wang, Zhonghua,Wu, Fanhong,Yin, Yan. "Superacid-catalyzed tandem Meyer–Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones". supporting information. p. 1249 - 1256. Retrieved 2016/08/16.
• 2、 Gosmini, Romain,Nguyen, Van Loc,Toum, Jér?me,Simon, Christophe,Brusq, Jean-Marie G.,Krysa, Gael,Mirguet, Olivier,Riou-Eymard, Alizon M.,Boursier, Eric V.,Trottet, Lionel,Bamborough, Paul,Clark, Hugh,Chung, Chun-Wa,Cutler, Leanne,Demont, Emmanuel H.,Kaur, Rejbinder,Lewis, Antonia J.,Schilling, Mark B.,Soden, Peter E.,Taylor, Simon,Walker, Ann L.,Walker, Matthew D.,Prinjha, Rab K.,Nicodème, Edwige. "The discovery of I-BET726 (GSK1324726A), a potent tetrahydroquinoline ApoA1 up-regulator and selective BET bromodomain inhibitor". . p. 8111 - 8131. Retrieved 2014/12/10.