8-Bromoisoquinoline

Base Information

• Chemical Name: 8-Bromoisoquinoline
• CAS No.: 63927-22-0
• Molecular Formula: C9H6BrN
• Molecular Weight: 208.057
• Hs Code.: 29334900
• European Community (EC) Number: 689-822-4
• DSSTox Substance ID: DTXSID40431935
• Nikkaji Number: J1.784.831C
• Wikidata: Q72445899
• Mol file: 63927-22-0.mol

Synonyms:8-Bromoisoquinoline;63927-22-0;8-Bromo-isoquinoline;Isoquinoline, 8-bromo-;MFCD04973298;D-Lactosyl fluoride;SCHEMBL197053;8-Bromoisoquinoline, AldrichCPR;DTXSID40431935;DPRIHFQFWWCIGY-UHFFFAOYSA-N;BCP26269;CS-B0667;BBL100520;STL554314;AKOS005254361;AC-1503;FS-2228;MB03403;HY-69089;PD020359;SY020013;A8788;AM20061400;B4144;FT-0602289;FT-0687342;EN300-102396;J-519404;J-803028;Z1269224644

Chemical Property of 8-Bromoisoquinoline

Chemical Property:

• Vapor Pressure: 0.0101mmHg at 25°C
• Melting Point: 80.5 °C
• Refractive Index: 1.59
• Boiling Point: 312.3 °C at 760 mmHg
• PKA: 4.63±0.23(Predicted)
• Flash Point: 142.7 °C
• PSA: 12.89000
• Density: 1.564 g/cm³
• LogP: 2.99730
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 206.96836
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99%min ^*data from raw suppliers

8-Bromoisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn,T
• Statements: 36/37/38-20/21/22-25
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=NC=C2)C(=C1)Br
• Uses: 8-Bromoisoquinoline is an intermediate used to prepare 4-?((2-?Hydroxy-?3-?methoxybenzyl)?amino)?benzenesulfonamide derivatives as potent and selective inhibitors of 12-?Lipoxygenase. It is also used in the synthesis of selective excitatory amino acid transporter subtype 1 (EAAT1) Inhibitor UCPH-?102.

Technology Process of 8-Bromoisoquinoline

There total 13 articles about 8-Bromoisoquinoline 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: 71.5%

ortho-bromobenzaldehyde (6630-33-7) + 2,2-dimethoxyethylamine (22483-09-6) → 8-bromo-isoquinoline (63927-22-0)

Guidance literature:

ortho-bromobenzaldehyde; 2,2-dimethoxyethylamine; In toluene; for 2h; Reflux; Dean-Stark;

With aluminum (III) chloride; In dichloromethane; at 0 - 45 ℃; for 16h;

Reference yield: 45.0%

8-aminoisoquinoline (23687-27-6) → 8-bromo-isoquinoline (63927-22-0)

Guidance literature:

8-aminoisoquinoline; With hydrogen bromide; sodium nitrite; at 0 - 5 ℃;

With copper(I) bromide;

DOI:10.1021/jm049025p

Reference yield: 1.8%

(2-bromobenzylidene)(2,2-dimethoxyethyl)amine (405161-29-7) → 8-bromo-isoquinoline (63927-22-0)

Guidance literature:

With sulfuric acid; at 130 - 140 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00573-2

upstream raw materials:

sulfuric acid

(2-bromo-benzylidenamino)-acetaldehyde diethylacetal

isoquinoline

(2-bromobenzylidene)(2,2-dimethoxyethyl)amine

Downstream raw materials:

8-bromo-1-(3,4-dimethoxy-benzyl)-isoquinoline

8-bromo-2H-isoquinolin-1-one

tert-butyl 2-(isoquinolin-8-yl)acetate

Refernces

• 1、 -. "HETEROCYCLIC COMPOUNDS AS EP4 RECEPTOR ANTAGONISTS". Paragraph 0222; 0223. . Retrieved 2016/05/09.
• 2、 Jiang, Rong,Duckett, Derek,Chen, Weiming,Habel, Jeff,Ling, Yuan Yuan,LoGrasso, Philip,Kamenecka, Theodore M.. "3,5-Disubstituted quinolines as novel c-Jun N-terminal kinase inhibitors". . p. 6378 - 6382. Retrieved 2008/09/16.