2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 61676-62-8
• Molecular Formula: C9H19BO3
• Molecular Weight: 186.059
• Hs Code.: 29209090
• European Community (EC) Number: 612-189-2
• DSSTox Substance ID: DTXSID20407552
• Nikkaji Number: J1.428.798A
• Wikidata: Q72485582
• Mol file: 61676-62-8.mol

Synonyms:61676-62-8;2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Isopropoxyboronic acid pinacol ester;isopropoxyboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane;2-ISOPROPOXY-4,4,5,5-DIMETHYL-1,3,2-DIOXABOROLANE;MFCD00192241;2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane;C9H19BO3;PINBOP;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1-methylethoxy)-;SCHEMBL9839;DTXSID20407552;MRWWWZLJWNIEEJ-UHFFFAOYSA-N;BCP12838;CS-D0245;STR09262;AKOS004116363;AB04651;AM20100506;FT-0612702;I0658;EN300-123725;ISOPROPYL DIHYDROGEN BORATE PINACOL ESTER;A833359;J-521562;isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-iso-propoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]-dioxaborolane;2-Isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane;2-iso-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane;2-isopropyloxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 98%;2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(Isopropoxyboronic acid pinacol ester;2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(Methoxyboronic acid pinacol ester)

Chemical Property of 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 4.924mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• Boiling Point: 150.306 °C at 760 mmHg
• Flash Point: 23.721 °C
• PSA: 27.69000
• Density: 0.925 g/cm³
• LogP: 2.00030
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.1427246
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)OC(C)C
• Uses: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes and to prepare fluorenylborolane.It can also be used in the synthesis of following intermediates for generating conjugated copolymers:9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole. suzuki reaction

Technology Process of 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 15 articles about 2-Isopropoxy-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: 93.0%

Isopropyl acetate (108-21-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-ethoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1126-93-8) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8)

Guidance literature:

With trimethylsilylmethyllithium; In neat (no solvent); at 20 ℃; for 6h; chemoselective reaction; Schlenk technique; Glovebox; Inert atmosphere;

DOI:10.1016/j.poly.2022.115784

Reference yield: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) → 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8)

Guidance literature:

In hexane;

DOI:10.1021/ja0058583

Reference yield: 87.5%

2,3-dimethyl-2,3-butane diol (76-09-5) + isopropoxyboronic acid (52732-22-6) → 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8)

Guidance literature:

Inert atmosphere; Reflux; Large scale reaction;

DOI:10.1021/ol900350k

upstream raw materials:

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

isopropyl alcohol

Triisopropyl borate

isopropoxyboronic acid

Downstream raw materials:

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

9,9-dioctylfluorene-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-hept-6-en-1-ynyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

4,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)[1,3,2]dioxaborolane

Refernces

• 1、 Stepanenko, Viatcheslav,De Jesús, Melvin,Garcia, Carmelo,Barnes, Charles L.,Ortiz-Marciales, Margarita. "Synthesis and stability of new spiroaminoborate esters". . p. 910 - 913. Retrieved 2012.
• 2、 James, Alexander P.,Lau, Samantha,Provis-Evans, Cei B.,Webster, Ruth L.. "Hydroboration of aldehydes, ketones and CO2under mild conditions mediated by iron(iii) salen complexes". supporting information. p. 10696 - 10700. Retrieved 2021/08/17.
• 3、 Cui, Dongmei,Li, Min,Liu, Xinli. "Catalytic hydroboration of carbonyl derivatives by using phosphinimino amide ligated magnesium complexes". supporting information. p. 13037 - 13041. Retrieved 2021/10/12.