4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane
• CAS No.: 83947-58-4
• Molecular Formula: C9H17BO2
• Molecular Weight: 168.044
• European Community (EC) Number: 693-264-7,805-000-1
• Nikkaji Number: J1.793.254C,J2.108.715G
• Wikidata: Q76416975
• Mol file: 83947-58-4.mol

Synonyms:83947-58-4;72824-05-6;4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane;Propen-1-ylboronic acid, pinacol ester;(E)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane;(E)-1-propenyl boronic pinacol ester;4,4,5,5-tetramethyl-2-[(E)-prop-1-enyl]-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-((E)-propenyl)[1,3,2]dioxaborolane;trans-1-Propenylboronic acid pinacol ester;MFCD15143598;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1E)-1-propenyl-;SCHEMBL11094;SCHEMBL1064325;COPMASWDWLENMV-VOTSOKGWSA-N;(E)-1-Propenylboronic Pinacol Ester;AKOS006334178;trans-propenylboronic acid pinacol ester;AS-55710;CS-0179249;A50025;EN300-761428;trans-1-Propenylboronic acid pinacol ester, 97%;Z1201628034;4,4,5,5-tetramethyl-2-((E)-propenyl)-[1,3,2]dioxaborolane;(E)-4,4,5,5-tetramethyl-2-(prop-1-enyl)-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane

Chemical Property:

• Refractive Index: n20/D1.433
• Boiling Point: 46-47℃ (4 Torr)
• Flash Point: 48.9±22.6℃
• PSA: 18.46000
• Density: 0.89±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 2.19390
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 168.1321599
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

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

trans-1-Propenylboronic acid pinacol ester 97% ^*data from reagent suppliers

Safty Information:

• Statements: 10

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4,4,5,5-Tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane

There total 11 articles about 4,4,5,5-Tetramethyl-2-(prop-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: 84.0%

(E)-propenyl lithium (6386-72-7,6524-17-0,29283-76-9) + 2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → pinacol 1-<1,1-dimethyl-2(E)-butenyl>boronate (96041-10-0) + 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane (72824-04-5,83947-58-4,83947-59-5,72824-05-6)

Guidance literature:

In diethyl ether; (E)-propenyllithium (6.87 mmol) in Et2O soln. was added dropwise during45 min under Ar to a soln. of 2-bromo-2-propylboronate (6.21 mmol) in Et2O at -78°C;; distn. at 68-70°C (5 mm Hg)gve the product (98% isomerically pure);

DOI:10.1021/ja00272a043

Reference yield: 82.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (E)-propenylboronic acid (6336-44-3,7547-96-8,88982-39-2,7547-97-9) → 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane (83947-58-4)

Guidance literature:

With magnesium sulfate; In diethyl ether; at 20 ℃; for 4h;

DOI:10.1021/ja044878s

Reference yield: 63.0%

acetaldehyde (75-07-0,9002-91-9) + 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) → 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane (83947-58-4)

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;

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

DOI:10.1021/acs.orglett.5b00480

upstream raw materials:

(Z)-1-propenyllithium

2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(Z)-1-propenylmagnesium bromide

(E)-propenyl lithium

Downstream raw materials:

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

C₂₄H₂₅NS

C₄₀H₆₈BNO₉Si

C₄₀H₆₈BNO₉Si

Refernces

• 1、 -. "ISOMERIZATION OF ALKENES". Page/Page column 20-21; 23. . Retrieved 2020/04/25.
• 2、 Kapat, Ajoy,Sperger, Theresa,Guven, Sinem,Schoenebeck, Franziska. "E-Olefins through intramolecular radical relocation". . p. 391 - 396. Retrieved 2019/02/03.