TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER
• CAS No.: 169339-75-7
• Molecular Formula: C13H25 B O2
• Molecular Weight: 224.151
• Hs Code.: 2934999090
• Mol file: 169339-75-7.mol

Synonyms:1,3,2-Dioxaborolane,2-(1-heptenyl)-4,4,5,5-tetramethyl-, (E)-; 1,3,2-Dioxaborolane, 2-(1E)-1-heptenyl-4,4,5,5-tetramethyl-(9CI)

Chemical Property of TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0.0561mmHg at 25°C
• Refractive Index: 1.445
• Boiling Point: 73-77℃/0.5mm
• Flash Point: 73-77℃/0.5mm
• PSA: 18.46000
• Density: 0.875
• LogP: 3.75430
• Storage Temp.: 2-8°C

Purity/Quality:

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

trans-1-HeptenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: trans-1-Hepten-1-ylboronic acid pinacol ester can be used in a palladium-catalyzed cross-coupling with olefins providing substituted 1,3-dienes. Substrate used in a palladium-catalyzed cross-coupling with olefins providing substituted 1,3-dienes.

Technology Process of TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER

There total 9 articles about TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER 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%

1-Heptyne (628-71-7) + bis(pinacol)diborane (73183-34-3) → (E)-2-(hept-1'-en-1'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (169339-75-7)

Guidance literature:

With ethanol; sodium methylate; at 22 ℃; for 2h; regioselective reaction;

DOI:10.1039/c8nj03708f

Reference yield: 85.0%

1-Heptyne (628-71-7) + bis(pinacol)diborane (73183-34-3) → (E)-2-(hept-1'-en-1'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (169339-75-7) + 2-(hept-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:

With bromobenzene; 2,2,2-trifluoroethanol; potassium tert-butylate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 80 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03416

Reference yield: 85.0%

hexanal (66-25-1) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → (E)-2-(hept-1'-en-1'-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (169339-75-7)

Guidance literature:

4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane; With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Inert atmosphere; Sealed tube;

hexanal; In tetrahydrofuran; at -78 ℃; for 4h; Temperature; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.5b00480

upstream raw materials:

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

1-Heptyne

trans-1-heptenylboronic acid

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

Downstream raw materials:

(E)-undec-5-en-2-one

(E)-3-(boronic acid pinacolate ester)-1-phenyl-1-nonene

Refernces

• 1、 Xia, Ming,Mutailipu, Miriding,Li, Fuming,Yang, Zhihua,Pan, Shilie. "Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point". supporting information. p. 9753 - 9757. Retrieved 2021/05/27.
• 2、 Gao, Ning,Hu, Tianding,Kang, Xiaomin,Lan, Xingwang,Wang, Zhenguang,Wu, Zhi-Lei,Zhao, Bin. "Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions". . p. 250 - 257. Retrieved 2021/10/25.