E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 69611-02-5
• Molecular Formula: C10H19 B O2
• Molecular Weight: 182.071
• Mol file: 69611-02-5.mol

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

Chemical Property of E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: n20/D 1.434
• Boiling Point: 68-76 °C(Press: 7 Torr)
• Flash Point: 63 °C
• PSA: 18.46000
• Density: 0.888 g/mL at 25 °C
• LogP: 2.65470
• Storage Temp.: 2-8°C

Purity/Quality:

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

trans-Crotylboronic acid pinacol ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 25 articles about E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-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: 84.0%

trans-2-butenyl acetate (7204-29-7) + bis(pinacol)diborane (73183-34-3) → (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-02-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; tricyclohexylphosphine; In ethyl acetate; at 60 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol3001552

Reference yield: 78.0%

2-chloro-3-butene (563-52-0,35729-37-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-02-5)

Guidance literature:

With Pt(dba)2; triphenyl-arsane; triethylamine; In toluene; at 50 ℃; for 16h;

DOI:10.1016/S0040-4039(00)00881-9

Reference yield: 73.0%

(E)-but-2-enol (504-61-0,542-72-3) + bis(pinacol)diborane (73183-34-3) → (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-02-5)

Guidance literature:

With [Pd(CH₃CN)(C₆H₃(CH₂SCH₃)2)]⁽¹⁺⁾*BF₄^(1-)=[Pd(CH₃CN)(C₆H₃(CH₂SCH₃)2)]BF₄; In chloroform; at 50 ℃; for 16h;

DOI:10.1021/jo9008673

upstream raw materials:

2-chloro-3-butene

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

1-chloro-2-butene

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

Downstream raw materials:

2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C₁₀H₁₉BO₂

(Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(anti)-4-hydroxy-3-methyl-6-phenyl-1-hexene

Refernces

• 1、 Camp, Andrew M.,Kita, Matthew R.,Blackburn, P. Thomas,Dodge, Henry M.,Chen, Chun-Hsing,Miller, Alexander J.M.. "Selecting double bond positions with a single cation-responsive iridium olefin isomerization catalyst". supporting information. p. 2792 - 2800. Retrieved 2021/03/01.
• 2、 Ge, Yicen,Cui, Xi-Yang,Tan, Siu Min,Jiang, Huan,Ren, Jingyun,Lee, Nicholas,Lee, Richmond,Tan, Choon-Hong. "Guanidine–Copper Complex Catalyzed Allylic Borylation for the Enantioconvergent Synthesis of Tertiary Cyclic Allylboronates". supporting information. p. 2382 - 2386. Retrieved 2019/02/01.