6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)isoquinoline

Base Information

• Chemical Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)isoquinoline
• CAS No.: 675576-26-8
• Molecular Formula: C15H18 B N O2
• Molecular Weight: 255.124
• Hs Code.: 2934999090
• European Community (EC) Number: 804-237-8
• DSSTox Substance ID: DTXSID80582879
• Wikidata: Q72507585
• Mol file: 675576-26-8.mol

Synonyms:675576-26-8;6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOQUINOLINE;Isoquinoline-6-boronic acid pinacol ester;SCHEMBL2232278;DTXSID80582879;LFALMDZWCMSBFO-UHFFFAOYSA-N;MFCD11227091;AKOS022173471;SB38244;A9049;EN300-1425735;Isoquinoline-6-boronic acid pinacol ester, 95%;Z2044761365;6-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ISOQUINOLINE;6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) isoquinoline;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (>85%)

Chemical Property of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)isoquinoline

Chemical Property:

• Vapor Pressure: 3.62E-06mmHg at 25°C
• Melting Point: 179-184°C
• Boiling Point: 397.5oC at 760 mmHg
• PKA: 5.03±0.14(Predicted)
• Flash Point: 194.2oC
• PSA: 31.35000
• Density: 1.1g/cm3
• LogP: 2.53400
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 255.1430590
• Heavy Atom Count: 19
• Complexity: 329

Purity/Quality:

NLT 98% ^*data from raw suppliers

Isoquinoline-6-boronic acid pinacol ester 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)C=NC=C3
• Uses: Useful boron compound for Suzuki coupling.

Technology Process of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)isoquinoline

There total 2 articles about 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)isoquinoline 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: 62.0%

6-bromo-isoquinoline (34784-05-9) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline (675576-26-8)

Guidance literature:

With anhydrous potassium acetate; In 1,4-dioxane; at 90 ℃; for 2h; Inert atmosphere;

Reference yield:

→ 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline (675576-26-8)

Guidance literature:

Reference yield: 92.0%

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline (675576-26-8) + C23H26BrN5O3 → C32H32N6O3

Guidance literature:

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline; C₂₃H₂₆BrN₅O₃; With potassium phosphate; In 1,4-dioxane; water; at 20 ℃; for 0.25h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 95 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.bmc.2021.116186

upstream raw materials:

6-bromo-isoquinoline

bis(pinacol)diborane

Downstream raw materials:

6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline

2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinolinium; iodide

2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline

6-phenylisoquinoline

Refernces

• 1、 -. "FUSED RING DERIVATIVE AS A2A RECEPTOR INHIBITOR". Paragraph 0122-0124. . Retrieved 2020/08/09.
• 2、 -. "Heterocyclic compound with Wnt signal path inhibitory activity and application thereof". Paragraph 0083; 0084; 0085. . Retrieved 2016/10/08.