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

Base Information

• Chemical Name: 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1195-66-0
• Molecular Formula: C7H15BO3
• Molecular Weight: 158.005
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00450364
• Nikkaji Number: J1.428.799J
• Wikidata: Q72486159
• Mol file: 1195-66-0.mol

Synonyms:2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1195-66-0;Methoxyboronic acid pinacol ester;methoxyboronic acid, pinacol ester;1,3,2-Dioxaborolane, 2-methoxy-4,4,5,5-tetramethyl-;MFCD03093086;SCHEMBL510041;C7H15BO3;DTXSID00450364;JZZJAWSMSXCSIB-UHFFFAOYSA-N;methoxy boronic acid pinacol ester;AKOS015850880;CS-W020633;SY026106;FT-0612791;M1714;METHYL DIHYDROGEN BORATE PINACOL ESTER;2-Methoxy-4455-tetramethyl-132-dioxaborolane;I10632;A804317;2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborole;J-200139;2-methoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane;2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 96%

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

Chemical Property:

• Vapor Pressure: 33.108mmHg at 25°C
• Refractive Index: 1.4096
• Boiling Point: 106.341 °C at 760 mmHg
• Flash Point: 3.279 °C
• PSA: 27.69000
• Density: 0.942 g/cm³
• LogP: 1.22170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.1114245
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

98% ^*data from raw suppliers

Methoxyboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)OC
• Uses: suzuki reaction It is employed in the synthesis, optical, and electrochemical properties of novel copolymers on the basis of benzothiadiazole and electron-rich arene units.

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

There total 97 articles about 2-Methoxy-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: 91.0%

methanol (67-56-1) + N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) + bis(pinacol)diborane (73183-34-3) → CH3C6H4SO2NHCH(BO2C2(CH3)4)C6H5 (1370281-63-2) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0)

Guidance literature:

With Cs₂CO₃; catalyst: PPh₃; In tetrahydrofuran; methanol; ligand and B comps. (1:1.2 molar ratio) at 70°C for 15 h; NMR;

DOI:10.1039/c2cc00020b

Reference yield: 85.0%

methanol (67-56-1) + bis(pinacol)diborane (73183-34-3) → 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) + hydrogen (1333-74-0)

Guidance literature:

With palladium (II) acetate; at 0 ℃; for 0.25h;

DOI:10.1021/acs.orglett.6b02508

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + RuH2(H2)2(tricyclohexylphosphine)2 (112320-11-3) + carbon dioxide (1111-72-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → [13C]-formaldehyde (3228-27-1,89277-65-6) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0)

Guidance literature:

RuH₂(H₂)2(tricyclohexylphosphine)2; carbon dioxide; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In benzene-d6; for 0.6h; under 760.051 Torr; Inert atmosphere;

formaldehyd; In benzene; for 24h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201304025

upstream raw materials:

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

Trimethyl borate

methyl (2E)-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-but-2-enoate

cis-Me(allyl)CCCOOEt(CH₂B(OCMe₂)2)

Downstream raw materials:

3-iodo-1-(phenylsulfonyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole

(MeOC₆H₄)(((CH₃)4C₂O₂)B)C₄H₂NCH₂CH₂C₆H₄OMe

2-(cyclooct-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Weetman, Catherine,Bag, Prasenjit,Szilvási, Tibor,Jandl, Christian,Inoue, Shigeyoshi. "CO2 Fixation and Catalytic Reduction by a Neutral Aluminum Double Bond". . p. 10961 - 10965. Retrieved 2019.
• 2、 Bandyopadhyay, Ayan,Bhattacharjee, Jayeeta,Kumar Singh, Saurabh,Kumari, Kusum,Moorthy, Shruti,Panda, Tarun K.,Sai Kumar, Gobbilla. "Hydroboration of nitriles, esters, and amides catalyzed by simple neosilyllithium". supporting information. . Retrieved 2022/03/31.
• 3、 Bao, Qin,Gao, Jianjian,Hong, Dongjing,Mu, Xiaolong,Song, Lulu,Wang, Shaowu,Wei, Yun,Zhou, Shuangliu,Zhu, Xiancui. "Synthesis and characterization of rare-earth metallate amido complexes bearing the 2-amidate-functionalized indolyl ligand and their application in the hydroboration of esters with pinacolborane". . p. 2953 - 2961. Retrieved 2022/02/21.