8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate)

Base Information

Chemical Name:8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate)
CAS No.:857934-95-3
Molecular Formula:C₂₂H₂₃BINO₅S
Molecular Weight:551.21
Hs Code.:
DSSTox Substance ID:DTXSID001114511

Synonyms:DTXSID001114511;8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate);857934-95-3

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Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate)

Chemical Property:

Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:551.04347
Heavy Atom Count:31
Complexity:734

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:B1(OC(C(O1)(C)C)(C)C)C2=CC(=C3C=CC=NC3=C2OS(=O)(=O)C4=CC=C(C=C4)C)I

Technology Process of 8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate)

There total 2 articles about 8-Quinolinol, 5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 8-(4-methylbenzenesulfonate) 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: 81.0%

: p-toluenesulfonic acid 5,7-diiodoquinolin-8-yl ester

: 1195-66-0
2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 1068-55-9
isopropylmagnesium chloride

: 857934-95-3
5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-8-yl 4-methylbenzenesulfonate

Guidance literature:: With ammonium chloride; In tetrahydrofuran; iPrMgCl in THF added to soln. at -78°C of C8H4NI2(SO2C6H5) in THFin dry, argon-flushed Schlenk tube; mixt. stirred for 2 h, until I/Mg e xchange; BO2(C(CH3)2)2(OCH3) added; allowed to warm to room. temp., 1 h;quenched with aq. soln. of NH4Cl; extrn. with Et2O; dried over Na2SO4; filtration, soln. evapd. in vac.;
DOI:10.1002/anie.200462928

Reference yield:

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 857934-95-3
5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-8-yl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 68 percent / 2 h / 68 °C

2.1: iPrMgCl*LiCl / tetrahydrofuran / 2 h / -78 °C

2.2: 81 percent / tetrahydrofuran / -78 - 20 °C

With TurboGrignard; In tetrahydrofuran;
DOI:10.1002/anie.200462928

Reference yield: 91.0%

: 857934-95-3
5-iodo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-8-yl 4-methylbenzenesulfonate

: 807329-97-1
TurboGrignard

: 106-95-6
allyl bromide

: 5-allyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-8-yl 4-methylbenzenesulfonate

Guidance literature:: With ammonium chloride; copper(I) cyanide di(lithium chloride); In tetrahydrofuran; iPrMgCl*LiCl in THF added to soln. at -78°C of BO2(C(CH2)2)2(C9H4NI(OTs)) (THF), dry, argon-flushed Schlenk tube; mixt. stirred for 1 h; CuCN*2LiCl (THF) added; stirred for 20 min; allyl bromide added; warm toroom. temp.; quenched with aq. NH4Cl; extrn. with Et2O and CH2Cl2; dried over Na2SO4; filtration, soln. evapd.in vac.; recrystn. from CH2Cl2;
DOI:10.1002/anie.200462928