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

Base Information

• Chemical Name: 2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 68716-51-8
• Molecular Formula: C12H15BCl2O2
• Molecular Weight: 272.967
• Hs Code.: 2934999090
• European Community (EC) Number: 675-094-5
• DSSTox Substance ID: DTXSID70374220
• Nikkaji Number: J1.689.012J
• Wikidata: Q82162736
• Mol file: 68716-51-8.mol

Synonyms:68716-51-8;2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3,5-Dichlorophenylboronic acid pinacol ester;3,5-dichlorophenylboronic acid, pinacol ester;MFCD05863906;1,3,2-DIOXABOROLANE, 2-(3,5-DICHLOROPHENYL)-4,4,5,5-TETRAMETHYL-;SCHEMBL587884;(3,5-DICHLOROPHENYL)BORONIC ACID PINACOL ESTER;DTXSID70374220;HKSNHZBPIBSVGI-UHFFFAOYSA-N;AKOS015951149;AB22697;CS-W000961;DS-17406;SY057174;D4575;EN300-1706215;3,5-DICHLOROPHENYLBORONICACID,PINACOLESTER;A836225;Z1336747738;3,5-Dichlorophenylboronic acid, pinacol ester, AldrichCPR;2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;1,3-Dichloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;2-(3,5-dichloro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, AldrichCPR

Chemical Property of 2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 8.51E-05mmHg at 25°C
• Melting Point: 51.0 to 55.0 °C
• Refractive Index: 1.52
• Boiling Point: 351.1 °C at 760 mmHg
• Flash Point: 166.1 °C
• PSA: 18.46000
• Density: 1.2 g/cm³
• LogP: 3.29260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 272.0542153
• Heavy Atom Count: 17
• Complexity: 270

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,5-Dichlorophenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)Cl

Technology Process of 2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 20 articles about 2-(3,5-Dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 95.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 1,3-Dichlorobenzene (541-73-1) → 2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (68716-51-8)

Guidance literature:

With IrH₂(Bpin){κ³-P,O,P-[9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene]}; cyclohexene; at 110 ℃; for 18h; Inert atmosphere; Glovebox;

DOI:10.1002/chem.202001838

Reference yield: 95.0%

bis(pinacol)diborane (73183-34-3) + 1,3-Dichlorobenzene (541-73-1) → 2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (68716-51-8)

Guidance literature:

bis(pinacol)diborane; With C₂₄H₂₈ClIrN₂O; In n-heptane; isopropyl alcohol; at 75 ℃; for 1h; Sealed tube; Inert atmosphere;

1,3-Dichlorobenzene; In n-heptane; isopropyl alcohol; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04210

Reference yield: 83.0%

1-bromo-3,5-dichlorobenzene (19752-55-7) + 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (68716-51-8)

Guidance literature:

With magnesium; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.12.033

upstream raw materials:

bis(pinacol)diborane

1,3-Dichlorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

(3,5-dichlorophenyl)boronic acid

3,5-dichloro-1-nitrobenzene

3,5-Dichloroaniline

1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Refernces

• 1、 Gao, Pengcheng,Szostak, Michal. "Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation". supporting information. p. 6010 - 6015. Retrieved 2020/07/30.
• 2、 Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel. "meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation". supporting information. p. 8018 - 8023. Retrieved 2019/05/29.