1-PENTENYLBORONIC ACID

Base Information

• Chemical Name: 1-PENTENYLBORONIC ACID
• CAS No.: 104376-24-1
• Molecular Formula: C₅H₁₁BO₂
• Molecular Weight: 113.952
• Hs Code.: 29310099
• Mol file: 104376-24-1.mol

Synonyms:Boronicacid, 1-pentenyl- (9CI);1-Penten-1-ylboronic acid;1-Pentenylboronic acid;

Chemical Property of 1-PENTENYLBORONIC ACID

Chemical Property:

• Appearance/Colour: White shinying small flake
• Vapor Pressure: 0.0452mmHg at 25°C
• Melting Point: 100-105 °C(lit.)
• Refractive Index: 1.435
• Boiling Point: 209.9 °C at 760 mmHg
• PKA: 9.81±0.43(Predicted)
• Flash Point: 80.7 °C
• PSA: 40.46000
• Density: 0.936 g/cm³
• LogP: 0.35470
• Storage Temp.: Refrigerator (+4°C)

Purity/Quality:

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

1-Penten-1-ylboronic acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-26 37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for:? ;Synthesis of 8-alkenylborondipyrromethene dyes via Liebeskind-Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPY1? ;Rhodium and palladium catalyzed substitution reactions with enyne acetates and carbonates2? ;Halogenation and protodeauration reactions of organogold phosphine complexes3? ;Lewis acid catalyzed Nazarov reaction4? ;Palladium-catalyzed tandem intramolecular C-N and intermolecular Suzuki coupling process5,6 Reactant for:Synthesis of 8-alkenylborondipyrromethene dyes via Liebeskind-Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPYRhodium and palladium catalyzed substitution reactions with enyne acetates and carbonatesHalogenation and protodeauration reactions of organogold phosphine complexesLewis acid catalyzed Nazarov reactionPalladium-catalyzed tandem intramolecular C-N and intermolecular Suzuki coupling process

Technology Process of 1-PENTENYLBORONIC ACID

There total 6 articles about 1-PENTENYLBORONIC ACID 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: 87.0%

(E)-pent-1-en-1-yl-1,3,2-benzodioxaborole (37494-02-3) → (E)-1-pentenylboronic acid (104376-24-1,59239-44-0)

Guidance literature:

With water; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2004.01.051

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + C5H9BrMg (38203-74-6,38203-82-6,114657-97-5) → (E)-1-pentenylboronic acid (104376-24-1,59239-44-0)

Guidance literature:

C₅H₉BrMg; With lithium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; diethyl ether; at 20 ℃; Inert atmosphere;

DOI:10.3390/molecules26061615

Reference yield:

dibromoborane dimethylsulfide (55671-55-1) + 1-Pentyne (627-19-0) + water (7732-18-5) → (E)-1-pentenylboronic acid (104376-24-1,59239-44-0)

Guidance literature:

dibromoborane dimethylsulfide; 1-Pentyne; In dichloromethane; at 0 - 20 ℃; for 4h;

water; In diethyl ether; for 0.25h; Cooling with ice;

DOI:10.1021/ol501309e

upstream raw materials:

tris(ethylenedioxyboryl)methane

butyraldehyde

(E)-pent-1-en-1-yl-1,3,2-benzodioxaborole

1-Pentyne

Downstream raw materials:

(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester

methyl 2-(E)-1-pentenyl-6-benzyloxybenzoate

2-[3-methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

(E)-N-(pent-1-en-1-yl)benzamide

Refernces

• 1、 Boylan, Amy,Li, Jian-Yuan,Lundy, Brian J.,May, Jeremy A.,Nguyen, Thien S.,Sundstrom, Sasha,Vallakati, Ravikrishna. "Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones". . . Retrieved 2021/06/16.
• 2、 Feng, Chao,Loh, Teck-Peng. "Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides". supporting information. p. 3444 - 3447. Retrieved 2014/07/21.