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

Base Information

• Chemical Name: (Z)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 69611-01-4
• Molecular Formula: C10H19 B O2
• Molecular Weight: 182.071
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80474043
• Nikkaji Number: J1.823.313D
• Wikidata: Q82303807
• Mol file: 69611-01-4.mol

Synonyms:69611-01-4;(Z)-2-(But-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;cis-Crotylboronic acid pinacol ester;CIS-2-BUTEN-1-YLBORONIC ACID, PINACOL ESTER;2-[(Z)-but-2-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;SCHEMBL2694129;2-[(2Z)-But-2-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;DTXSID80474043;ARSSMJZIAKUXEW-SREVYHEPSA-N;MFCD09842772;AKOS015999639;BS-22591;cis-Crotylboronic acid pinacol ester, 97%;CS-0129387;A866799;2-[(Z)-but-2-enyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

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

Chemical Property:

• Refractive Index: n20/D 1.435
• Flash Point: 63 °C
• PSA: 18.46000
• Density: 0.884 g/mL at 25 °C
• LogP: 2.65470
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 182.1478100
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

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

Cis-2-buten-1-ylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

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

There total 25 articles about (Z)-2-(But-2-en-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: 80.0%

2-(but-3-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-01-4)

Guidance literature:

With [1,3-bis(diphenylphosphino)propane]nickel(II) bromide; diphenylphosphane; zinc(II) iodide; zinc; In dichloromethane; at -40 ℃; for 3h; diastereoselective reaction; Catalytic behavior; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.5b01230

Reference yield: 78.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (Z)-2-Butene (590-18-1) + fluorodimethoxyborane (367-46-4) → (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-01-4)

Guidance literature:

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; dichloromethane; soln. of (Z)-2-butene (87 mmol, THF, Ar) was treated with KO-t-Bu (85.2mmol) and n-BuLi (85.1 mmol) (hexane, -78°C, 15 min); addn. of FB(OMe)2 (89.4 mmol) for 1 h; extn. of crotylboronic acid (Et2O); addn. of pinacol (0.102 mmol); concn. gave an oil that was distd. (72-78°C, > 5 mm Hg); the product was 97% isomeric purity;

DOI:10.1021/ja00272a043

Reference yield:

(E/Z)-crotyl bromide (4784-77-4,29576-14-5,39616-19-8) + bis(pinacol)diborane (73183-34-3) → (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-01-4) + (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-02-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; at 60 ℃; for 18h; Overall yield = 34 percent; Overall yield = 905 mg; Inert atmosphere;

DOI:10.1055/s-0039-1690091

upstream raw materials:

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

(Z)-2-Butene

fluorodimethoxyborane

(Z)-1-propenyllithium

Downstream raw materials:

(2S,1'R,2'R)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

(2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

(2S,1'S,2'R)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

(2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine

Refernces

• 1、 Dennis, Francesca M.,Partridge, Benjamin M.,Robertson, Craig C.. "Nickel-Catalysed Allylboration of Aldehydes". . p. 1903 - 1914. Retrieved 2020/07/04.
• 2、 Becica, Joseph,Glaze, Owen D.,Wozniak, Derek I.,Dobereiner, Graham E.. "Selective Isomerization of Terminal Alkenes to (Z)-2-Alkenes Catalyzed by an Air-Stable Molybdenum(0) Complex". . p. 482 - 490. Retrieved 2018/02/17.