2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile

Base Information

• Chemical Name: 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile
• CAS No.: 883899-02-3
• Molecular Formula: C13H16 B N O3
• Molecular Weight: 245.086
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00470628
• Nikkaji Number: J2.307.655A
• Wikidata: Q82298780
• Mol file: 883899-02-3.mol

Synonyms:883899-02-3;2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile;2-CYANO-3-METHOXYPHENYLBORONIC ACID NEOPENTYL GLYCOL ESTER;Benzonitrile, 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxy-;SCHEMBL2662281;DTXSID00470628;RSLUOIPQHDWWMU-UHFFFAOYSA-N;MFCD08669558;AKOS015999756;AB45902;BS-24017;CS-0174073;D96318;A862210

Chemical Property of 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile

Chemical Property:

• PSA: 51.48000
• LogP: 1.33508
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 245.1223235
• Heavy Atom Count: 18
• Complexity: 328

Purity/Quality:

98%min ^*data from raw suppliers

2-Cyano-3-methoxyphenylboronicacidneopentylglycolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=C(C(=CC=C2)OC)C#N

Technology Process of 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile

There total 1 articles about 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile 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: 96.0%

Triisopropyl borate (5419-55-6) + 2-methoxy-benzonitrile (6609-56-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile (883899-02-3)

Guidance literature:

Triisopropyl borate; 2-methoxy-benzonitrile; With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

2,2-Dimethyl-1,3-propanediol; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

DOI:10.1021/jo052400g

Reference yield: 66.0%

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile (883899-02-3) + 9-amino-5-bromo-2-cyclobutyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one (1093951-28-0) → 2-(9-Amino-2-cyclobutyl-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-5-yl)-6-methoxybenzonitrile (1093948-88-9)

Guidance literature:

With potassium fluoride; tri tert-butylphosphoniumtetrafluoroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; at 90 ℃; for 2 - 24h;

Reference yield: 59.0%

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methoxybenzonitrile (883899-02-3) + 1-bromo-2-iodo-4,5-(methylenedioxy)benzene (94670-76-5) → 2-(6-bromobenzo[d][1,3]dioxol-5-yl)-6-methoxybenzonitrile

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; tripotassium phosphate "n" hydrate; In toluene; at 100 ℃; for 5h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.5b00544

upstream raw materials:

Triisopropyl borate

2-methoxy-benzonitrile

2,2-Dimethyl-1,3-propanediol

Downstream raw materials:

2-(9-Amino-2-cyclobutyl-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-5-yl)-6-methoxybenzonitrile

Refernces

• 1、 Lysen, Morten,Hansen, Henriette M.,Begtrup, Mikael,Kristensen, Jesper L.. "Synthesis of substituted 2-cyanoarylboronic esters". . p. 2518 - 2520. Retrieved 2007/10/03.