5-Bromoisoquinoline

Base Information

• Chemical Name: 5-Bromoisoquinoline
• CAS No.: 34784-04-8
• Molecular Formula: C9H6BrN
• Molecular Weight: 208.057
• Hs Code.: 29334900
• European Community (EC) Number: 626-788-1
• DSSTox Substance ID: DTXSID70353035
• Nikkaji Number: J1.716.314K
• Wikidata: Q72445897
• Mol file: 34784-04-8.mol

Synonyms:5-Bromoisoquinoline;34784-04-8;5-Bromo-isoquinoline;ISOQUINOLINE, 5-BROMO-;5-Bromoisoquinolin;MFCD01646405;5-Bromo isoquinoline;5-Bromoisoquinoline, 98%;SCHEMBL196671;DTXSID70353035;CYJZJGYYTFQQBY-UHFFFAOYSA-N;BBL100338;STK023322;AKOS000268560;AB09627;AC-2582;CS-W007854;FS-2226;HY-W007854;PD020362;SY002213;AM20061871;B3313;EU-0081044;FT-0620164;EN300-39298;AE-842/31875011;SR-01000506847;SR-01000506847-1;W-202424;Z57204608;F0918-4369

Chemical Property of 5-Bromoisoquinoline

Chemical Property:

• Appearance/Colour: White to yellow-brown crystals
• Vapor Pressure: 0.000977mmHg at 25°C
• Melting Point: 83-87 °C(lit.)
• Refractive Index: 1.673
• Boiling Point: 312.3 °C at 760 mmHg
• PKA: 4.39±0.13(Predicted)
• Flash Point: 142.7 °C
• PSA: 12.89000
• Density: 1.564 g/cm³
• LogP: 2.99730
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• 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:

98% HPLC ^*data from raw suppliers

5-Bromoisoquinolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CN=C2)C(=C1)Br
• Description: 5-Bromoisoquinoline is a synthetic intermediate useful for pharmaceutical synthesis.
• Uses: Starting material employed in palladium-catalyzed aminomethylation1 and amination2 reactions. Starting material employed in palladium-catalyzed aminomethylation and amination reactions.

Technology Process of 5-Bromoisoquinoline

There total 16 articles about 5-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: 87.0%

5-bromoisoquinolin-2-ium-2-olate (223671-17-8) → 5-bromoisoquinoline (34784-04-8)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In acetonitrile; at 20 ℃; for 0.0833333h; chemoselective reaction; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.0c02805

Reference yield: 81.0%

isoquinoline (119-65-3) → 5-bromoisoquinoline (34784-04-8)

Guidance literature:

isoquinoline; With N-Bromosuccinimide; sulfuric acid; at -25 - 20 ℃;

With ammonia; In water; at 0 ℃; pH=8 - 10;

Reference yield: 81.0%

isoquinolin-5-ylamine (1125-60-6) → 5-bromoisoquinoline (34784-04-8)

Guidance literature:

With potassium nitrite; hydrogen bromide; dimethyl sulfoxide; copper(I) bromide; In water; at 35 ℃; for 0.5h;

DOI:10.1139/v05-026

upstream raw materials:

isoquinoline

sulfuric acid

(3-bromo-benzylidenamino)-acetaldehyde diethylacetal

isoquinolin-5-ylamine

Downstream raw materials:

isoquinoline-5-carboxaldehyde

5-methylisoquinoline

4-Isoquinoline-5-yl-piperazine-1-carboxylic acid tert-butyl ester

5-(3-nitrophenyl)-isoquinoline

Refernces

• 1、 Bastrakov,Starosotnikov. "Synthesis of novel polyfunctional pyrrolo[2,1-a]isoquinolines based on 1,3-dipolar cycloaddition reactions". . p. 1729 - 1734. Retrieved 2019.
• 2、 Czako, Barbara,Kuerti, Laszlo,Mammoto, Akiko,Ingber, Donald E.,Corey. "Discovery of potent and practical antiangiogenic agents inspired by cortistatin A". . p. 9014 - 9019. Retrieved 2009.
• 3、 Sit, Sing-Yuen,Xie, Kai,Jacutin-Porte, Swanee,Taber, Matthew T.,Gulwadi, Amit G.,Korpinen, Carolyn D.,Burris, Kevin D.,Molski, Thaddeus F.,Ryan, Elaine,Xu, Cen,Wong, Henry,Zhu, Juliang,Krishnananthan, Subramaniam,Gao, Qi,Verdoorn, Todd,Johnson, Graham. "(+)-Dinapsoline: An efficient synthesis and pharmacological profile of a novel dopamine agonist". . p. 3660 - 3668. Retrieved 2002.
• 4、 Jha, Neha,Singh, Roushan Prakash,Saxena, Paridhi,Kapur, Manmohan. "Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion". supporting information. p. 8694 - 8698. Retrieved 2021/11/24.
• 5、 Brindisi, Margherita,Ulivieri, Cristina,Alfano, Gloria,Gemma, Sandra,de Asís Balaguer, Francisco,Khan, Tuhina,Grillo, Alessandro,Chemi, Giulia,Menchon, Grégory,Prota, Andrea E.,Olieric, Natacha,Lucena-Agell, Daniel,Barasoain, Isabel,Diaz, J. Fernando,Nebbioso, Angela,Conte, Mariarosaria,Lopresti, Ludovica,Magnano, Stefania,Amet, Rebecca,Kinsella, Paula,Zisterer, Daniela M.,Ibrahim, Ola,O'Sullivan, Jeff,Morbidelli, Lucia,Spaccapelo, Roberta,Baldari, Cosima,Butini, Stefania,Novellino, Ettore,Campiani, Giuseppe,Altucci, Lucia,Steinmetz, Michel O.,Brogi, Simone. "Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents". . p. 290 - 320. Retrieved 2018/11/24.