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

Base Information

• Chemical Name: (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane
• CAS No.: 161395-96-6
• Molecular Formula: C₁₁H₂₁BO₂
• Molecular Weight: 196.098
• Hs Code.: 2934999090
• European Community (EC) Number: 681-359-6
• DSSTox Substance ID: DTXSID00570091
• Nikkaji Number: J3.014.947E,J2.704.040C
• Wikidata: Q82457429
• Mol file: 161395-96-6.mol

Synonyms:161395-96-6;(E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane;(E)-1-Pentene-1-boronic Acid Pinacol Ester;4,4,5,5-tetramethyl-2-[(E)-pent-1-enyl]-1,3,2-dioxaborolane;trans-1-Penten-1-ylboronic acid pinacol ester;(E)-1-PENTENYLBORONIC ACID PINACOL ESTER;E-PENTEN-1-YLBORONIC ACID, PINACOL ESTER;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1E)-1-penten-1-yl-;MFCD05663882;trans-1-Pentenyl-1-boronic acid pinacol ester;IMIHEZMTQOARIK-CMDGGOBGSA-N;1-PENTENYL-1-BORONIC ACID,PINACOL ESTER;SCHEMBL1628914;SCHEMBL2063732;DTXSID00570091;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1E)-1-pentenyl-;AKOS015910439;1-Pentenyl-1-boronic acid pinacol ester;(E)-pent-1-enylboronic acid pinacol ester;CS-0152593;J-009823;trans-1-Penten-1-ylboronic acid pinacol ester, 97%;trans-1-Penten-1-ylboronic acid pinacol ester, AldrichCPR;(E)-2-(1-Pentenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(e)-4,4,5,5-tetramethyl-2-(pent-1-enyl)-1,3,2-dioxaborolane;4,4,5,5-TETRAMETHYL-2-[(1E)-PENT-1-EN-1-YL]-1,3,2-DIOXABOROLANE

Chemical Property of (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.442mmHg at 25°C
• Refractive Index: n20/D 1.441
• Boiling Point: 110-111℃28mmHg
• Flash Point: 181℉
• PSA: 18.46000
• Density: 0.884g/mLat25℃
• LogP: 2.97410
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 196.1634601
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

97% ^*data from raw suppliers

trans-1- ^*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=CCCC
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/CCC
• Uses: (E)-1-Pentenylboronic Acid Pinacol Ester is a reagent in the BACE-1 inhibitory activity of acyl guanidines.

Technology Process of (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane

There total 13 articles about (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-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: 88.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (E)-1-pentenylboronic acid (104376-24-1,59239-44-0) → (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane (161395-96-6)

Guidance literature:

In tetrahydrofuran; for 0.5h;

DOI:10.1016/j.tet.2013.03.068

Reference yield: 82.0%

1-Pentyne (627-19-0) + bis(pinacol)diborane (73183-34-3) → (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane (161395-96-6)

Guidance literature:

With sodium methylate; copper; In ethanol; at 25 ℃; for 11h; regioselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/c3cc48670b

Reference yield: 56.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-Pentyne (627-19-0) + benzo[1,3,2]dioxaborole (274-07-7) → (Z)-4,4,5,5-tetramethyl-2-(pent-1-enyl)-1,3,2-dioxaborolane (1352747-94-4,161395-96-6)

Guidance literature:

1-Pentyne; benzo[1,3,2]dioxaborole; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine; tris(1-methylethyl)phosphine; In cyclohexane; at 20 ℃; for 2h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In cyclohexane; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0035-1561278

upstream raw materials:

1-Pentyne

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

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

(E)-1-pentenylboronic acid

Downstream raw materials:

C₁₂H₁₅NO₃

C₁₃H₁₈O₂

C₁₃H₁₈O

C₁₃H₁₈O