(E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

Base Information

• Chemical Name: (E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol
• CAS No.: 581802-26-8
• Molecular Formula: C11H21BO3
• Molecular Weight: 212.097
• Hs Code.: 2934999090
• Nikkaji Number: J1.932.366H,J2.681.682C
• Mol file: 581802-26-8.mol

Synonyms:581802-26-8;(E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol;(3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol;2-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BUT-3-EN-2-OL;SCHEMBL2043359;SCHEMBL2043363;FBCZPBPTNCLUII-BQYQJAHWSA-N;MFCD10698506;AKOS016007402;DS-17321;EN300-6285958;A869509;Z1509668330;(E)-(3-hydroxy-3-methylbut-1-en-1-yl)boronic acid pinacol ester;(3E)-2-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol;(E)-2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-en-2-ol;(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-3-butene-2-ol;2-(3-Hydroxy-3-methyl-1-butenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2129163-96-6

Chemical Property of (E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

Chemical Property:

• Boiling Point: 70-80 °C(Press: 0.1 Torr)
• PKA: 14.71±0.29(Predicted)
• PSA: 38.69000
• Density: 0.97±0.1 g/cm3(Predicted)
• LogP: 1.94490
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 212.1583747
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

97% ^*data from raw suppliers

(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=CC(C)(C)O
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C(C)(C)O

Technology Process of (E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

There total 8 articles about (E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol 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: 97.0%

2-methyl-but-3-yn-2-ol (115-19-5) + bis(pinacol)diborane (73183-34-3) → (E)-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl-2-ol (581802-26-8)

Guidance literature:

With sodium methylate; Cu⁽²⁺⁾*4Cu⁽¹⁺⁾*4I^(1-)*2C₅H₃N₂O₂^(1-)*C₅H₅N*C₂H₇N*3C₃H₇NO; In ethanol; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.jcat.2021.09.033

Reference yield: 81.0%

3-methyl-3-(trimethylsiloxy)-1-butyne (17869-77-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl-2-ol (581802-26-8)

Guidance literature:

With platinum(II) chloride; XPhos; In tetrahydrofuran; at 50 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c1cc14433b

Reference yield: 61.0%

2-methyl-but-3-yn-2-ol (115-19-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl-2-ol (581802-26-8)

Guidance literature:

With di(rhodium)tetracarbonyl dichloride; trifuran-2-yl-phosphane; In toluene; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1055/s-0036-1588977

upstream raw materials:

2-methyl-3-buten-2-ol

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

(E)-trimethyl((2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl)oxy)silane

3-methyl-3-(trimethylsiloxy)-1-butyne

Downstream raw materials:

6-({2,6-dichloro-4-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]phenyl}amino)pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one