(Z)-2-Buten-2-ylboronic acid pinacol ester

Base Information

• Chemical Name: (Z)-2-Buten-2-ylboronic acid pinacol ester
• CAS No.: 91890-00-5
• Molecular Formula: C10H19BO2
• Molecular Weight: 182.071
• European Community (EC) Number: 626-179-0,871-000-3
• Wikidata: Q76423134
• Mol file: 91890-00-5.mol

Synonyms:(Z)-2-Buten-2-ylboronic acid pinacol ester;91890-00-5;(Z)-2-(but-2-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(Z)-but-2-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(E)-2-(But-2-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;91890-02-7;SCHEMBL8755352;2-Buten-2-ylboronicacidpinacolester;MFCD23381515;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(1Z)-1-methyl-1-propen-1-yl]-;CS-0129371;EN300-380996;EN300-7473222;Z3245419224;2-[(2Z)-but-2-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (Z)-2-Buten-2-ylboronic acid pinacol ester

Chemical Property:

• PSA: 18.46000
• LogP: 2.58400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 182.1478100
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

97% ^*data from raw suppliers

(Z)-2-Buten-2-ylboronicacidpinacolester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of (Z)-2-Buten-2-ylboronic acid pinacol ester

There total 4 articles about (Z)-2-Buten-2-ylboronic 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: 96.0%

dimethylacetylene (503-17-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (2Z)-2-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)but-2-ene (91890-00-5,91890-02-7)

Guidance literature:

With tris(2,4,6-trifluorophenyl)borane triethylphosphine oxide; In dichloromethane; at 60 ℃; for 6h; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703109

Reference yield: 91.0%

2-(but-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (2Z)-2-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)but-2-ene (91890-00-5,91890-02-7)

Guidance literature:

With C₂₇H₄₀Cl₂FeN₃P; sodium triethylborohydride; In pentane; at 20 ℃; for 2h; stereoselective reaction;

DOI:10.1021/acscatal.1c02432

Reference yield:

4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane (75851-67-1) → (2Z)-2-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)but-2-ene (91890-00-5,91890-02-7) + (E)-2-(but-2-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91890-02-7)

Guidance literature:

With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); In tetrahydrofuran; at 60 ℃; for 16h; Overall yield = 92 percent; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/d0sc02542a

upstream raw materials:

dimethylacetylene

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

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

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

Downstream raw materials:

(2E,4S)-3-methyl-4-phenyl-4-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)hex-2-ene

(2S,3E)-3-methyl-2-phenyl-2-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)pent-3-ene