3,5-Dichlorophenylboronic acid

Base Information

• Chemical Name: 3,5-Dichlorophenylboronic acid
• CAS No.: 67492-50-6
• Molecular Formula: C6H5BCl2O2
• Molecular Weight: 190.821
• Hs Code.: 29319090
• European Community (EC) Number: 628-675-2
• DSSTox Substance ID: DTXSID70370222
• Nikkaji Number: J732.735H
• Wikidata: Q72467337
• Mol file: 67492-50-6.mol

Synonyms:3,5-Dichlorophenylboronic acid;67492-50-6;(3,5-dichlorophenyl)boronic Acid;3,5-Dichlorobenzeneboronic Acid;3,5-Dichlorophenyl boronic acid;MFCD00051935;3,5-dichrolo phenyl boronic acid;(3,5-dichlorophenyl)boranediol;3,5-Dichlorophenylboronicacid;3,5-dichloro phenylboronic acid;(3,5-DICHLOROPHENYL)DIHYDROXYBORANE;SCHEMBL177673;3,5-dichloro-phenylboronic acid;3,5-dichlorophenyl)boronic acid;3,5-dichlorophenyl-boronic acid;3,5-dichloro benzeneboronic acid;3,5-dichlorobenzene boronic acid;DTXSID70370222;3, 5-dichlorophenyl boronic acid;3,5-dichloro phenyl boronic acid;DKYRKAIKWFHQHM-UHFFFAOYSA-N;3,5-dichlorophenyl-dihydroxyborane;CS-D1010;3,5-Dichlorophenylboronic acid, 98%;AKOS004116174;AB02153;AC-5382;GS-6883;SY015732;A9040;AM20060218;D2909;FT-0614556;EN300-59198;Q-102206;Q-102936;[3,5-bis(chloranyl)phenyl]-oxidanyl-oxidanylidene-boron;Z401461948

Chemical Property of 3,5-Dichlorophenylboronic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.5E-05mmHg at 25°C
• Melting Point: 315 °C
• Refractive Index: 1.577
• Boiling Point: 351.7 °C at 760 mmHg
• PKA: 6.58±0.10(Predicted)
• Flash Point: 166.5 °C
• PSA: 40.46000
• Density: 1.47 g/cm³
• LogP: 0.67320
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 189.9759650
• Heavy Atom Count: 11
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dichlorobenzeneboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,F
• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-22-19-11
• Safety Statements: 26-36-37/39-33-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)Cl)Cl)(O)O
• Uses: Reactant involved in:? ;Suzuki-Miyaura cross-coupling1,2? ;Trifluoromethylation3? ;Intramolecular aromatic carbenoid insertion of biaryldiazoacetates4? ;Cyanation for the synthesis of aromatic nitriles5? ;Lithiation of dihalophenyl dioxazaborocines for synthesis of functionalized dihalophenyl boronic acid6 suzuki reaction 3,5-Dichlorobenzeneboronic Acid, is an intermediate for the synthesis of various pharmaceutical compounds including inhibitors. 3,5-Dichlorobenzeneboronic Acid was also found to facilitate the transport of various ribonucleosides in and out of liposomes (artificial cells).

Technology Process of 3,5-Dichlorophenylboronic acid

There total 4 articles about 3,5-Dichlorophenylboronic acid 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:

Triisopropyl borate (5419-55-6) + 3,5-dichloroiodobenzene (3032-81-3) → (3,5-dichlorophenyl)boronic acid (67492-50-6)

Guidance literature:

With n-butyllithium;

Reference yield:

1,3-Dichlorobenzene (541-73-1) → (3,5-dichlorophenyl)boronic acid (67492-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4,4'-di-tert-butyl-2,2'-bipyridine / [Ir(COD)(OMe)]2 / tetrahydrofuran / 16 h / 80 °C

2.1: sodium periodate / tetrahydrofuran; H₂O / 0.25 h

2.2: HCl / H₂O; tetrahydrofuran / 4 h

With sodium periodate; 4,4'-di-tert-butyl-2,2'-bipyridine; [Ir(COD)(OMe)]2; In tetrahydrofuran; water;

DOI:10.1021/ol062903o

Reference yield:

1-bromo-3,5-dichlorobenzene (19752-55-7) → (3,5-dichlorophenyl)boronic acid (67492-50-6)

Guidance literature:

1-bromo-3,5-dichlorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

With ammonium chloride; In tetrahydrofuran; hexane; at 20 ℃; Further stages.;

DOI:10.1021/jo062543i

upstream raw materials:

2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-bromo-3,5-dichlorobenzene

1,3-Dichlorobenzene

Triisopropyl borate

Downstream raw materials:

3',5'-Dichloro-2-methanesulfonyl-5-methyl-biphenyl-4-carboxylic acid methyl ester

2-{2-[2-(3,5-Dichloro-phenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione

3-iodobenzylalcohol

(3',5'-Dichloro-biphenyl-3-yl)-methanol

Refernces

• 1、 Murphy, Jaclyn M.,Tzschucke, C. Christoph,Hartwig, John F.. "One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes". . p. 757 - 760. Retrieved 2007/10/03.
• 2、 -. "Insecticidal substituted-2,4-diaminoquinazolines". . . Retrieved 2008/06/13.