6-Bromo-2H-isoquinolin-1-one

Base Information

• Chemical Name: 6-Bromo-2H-isoquinolin-1-one
• CAS No.: 82827-09-6
• Molecular Formula: C9H6 Br N O
• Molecular Weight: 224.057
• Hs Code.: 2933790090
• European Community (EC) Number: 810-437-6
• DSSTox Substance ID: DTXSID80579123
• Nikkaji Number: J2.581.276J
• Wikidata: Q72445931
• Mol file: 82827-09-6.mol

Synonyms:6-Bromo-2H-isoquinolin-1-one;82827-09-6;6-bromoisoquinolin-1(2H)-one;6-bromoisoquinolin-1-ol;6-bromo-1,2-dihydroisoquinolin-1-one;6-BROMOISOQUINOLIN-1-ONE;MFCD07374394;6-Bromo-1-hydroxyisoquinoline;6-bromo-1(2H)-Isoquinolinone;1(2H)-Isoquinolinone, 6-bromo-;6-Bromoisoquinolone;SCHEMBL7588;6-bromo-1-hydroxylisoquinoline;DTXSID80579123;ZDYXSEQHOVSTPA-UHFFFAOYSA-N;CS-B0782;AKOS015834789;AKOS022530718;AB39354;FS-2806;GS-4277;6-BROMO-2H-ISOQUINOLINE-1-ONE;s10300;AC-28293;SY025972;AM20061526;EN300-86225;A23410;J-518329;6-Bromoisoquinolin-1(2H)-one;Z1741974434

Chemical Property of 6-Bromo-2H-isoquinolin-1-one

Chemical Property:

• Boiling Point: 442.634 °C at 760 mmHg
• PKA: 12.20±0.20(Predicted)
• Flash Point: 221.498 °C
• PSA: 32.86000
• Density: 1.62 g/cm³
• LogP: 2.29060
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 222.96328
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Bromo-2H-isoquinolin-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CNC2=O)C=C1Br
• Uses: 6-Bromo-2H-isoquinolin-1-one was used as a reagent in the fragment-based discovery of ROCK-I inhibitors derived from 6-substituted isoquinolin-1-amine and also used in the discovery of novel isoquinolone PDK1 inhibitors which offer a potentially new therapeutic modality for cancer treatment.

Technology Process of 6-Bromo-2H-isoquinolin-1-one

There total 14 articles about 6-Bromo-2H-isoquinolin-1-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: 70.0%

vinyl acetate (108-05-4,9003-20-7) + (4-bromophenyl)formamido 2,2-dimethylpropanoate (1352801-45-6) → 6-bromo-2H-isoquinoline-1-one (82827-09-6)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; In methanol; at 45 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol502095z

Reference yield: 53.0%

n-vinylformamide (13162-05-5,72018-12-3) + 4-Bromobenzoic acid (586-76-5) → 6-bromo-2H-isoquinoline-1-one (82827-09-6)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; potassium hydrogencarbonate; In benzonitrile; at 80 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.orglett.9b03638

Reference yield: 53.0%

→ 6-bromo-2H-isoquinoline-1-one (82827-09-6)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; potassium hydrogencarbonate; In benzonitrile; at 80 ℃; for 24h;

upstream raw materials:

6-bromo-isoquinoline

3-Bromocinnamic acid

6-bromo-1-chloroisoquinoline

(E)-4-bromo-2-(2-(dimethylamino)vinyl)benzonitrile

Downstream raw materials:

6-bromo-1-chloroisoquinoline

C₃₅H₂₆BrNO₈

1-benzyloxy-6-bromo-isoquinoline

6-bromo-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one

Refernces

• 1、 -. "Aromatic compounds and preparation method and application thereof". Paragraph 0012; 0037-0039; 0067-0068. . Retrieved 2020/02/19.
• 2、 Devine, William,Woodring, Jennifer L.,Swaminathan, Uma,Amata, Emanuele,Patel, Gautam,Erath, Jessey,Roncal, Norma E.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Mensa-Wilmot, Kojo,Sciotti, Richard J.,Pollastri, Michael P.. "Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery". supporting information. p. 5522 - 5537. Retrieved 2015/08/03.