Cyclopenten-1-ylboronic acid

Base Information

• Chemical Name: Cyclopenten-1-ylboronic acid
• CAS No.: 850036-28-1
• Molecular Formula: C₅H₉BO₂
• Molecular Weight: 111.936
• Hs Code.: 29319090
• European Community (EC) Number: 691-688-7
• DSSTox Substance ID: DTXSID40397507
• Wikidata: Q82198922
• Mol file: 850036-28-1.mol

Synonyms:cyclopenten-1-ylboronic acid;850036-28-1;cyclopent-1-en-1-ylboronic acid;1-cyclopentenylboronic Acid;(Cyclopent-1-en-1-yl)boronic acid;cyclopenten-1-yl boronic acid;1-cyclopenteneboronic acid;CYCLOPENTENE-1-BORONIC ACID;Boronic acid, 1-cyclopenten-1-yl-;MFCD02179496;cyclopentenylboronic acid;C5H9BO2;cyclopenteneboronic acid;Cyclopentene-l-boronic acid;Cyclopent-1-enyl boronic acid;cyclopent-1-enyl-boronic acid;SCHEMBL336524;1-cyclopenten-1-ylboronic acid;AMY982;Cyclopent-1-ene-1-boronic acid;DTXSID40397507;UZBHNSVUMGIKLU-UHFFFAOYSA-N;CYCLOPENTEN-1-YLBORONICACID;BCP21607;AKOS006230633;AB11270;CS-W000981;GS-5857;cyclopenten-1-ylboronic acid, AldrichCPR;AC-31778;SY026107;C2893;FT-0687754;EN300-126090;A863828;Z1201621640;1-Cyclopenteneboronic Acid;Cyclopentenylboronic acid

Chemical Property of Cyclopenten-1-ylboronic acid

Chemical Property:

• Vapor Pressure: 0.00439mmHg at 25°C
• Melting Point: 134-140 °C
• Refractive Index: 1.482
• Boiling Point: 246.7 °C at 760 mmHg
• PKA: 9.44±0.20(Predicted)
• Flash Point: 103 °C
• PSA: 40.46000
• Density: 1.08 g/cm³
• LogP: 0.10870
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 112.0695597
• Heavy Atom Count: 8
• Complexity: 109

Purity/Quality:

98% ^*data from raw suppliers

Cyclopenten-1-ylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CCCC1)(O)O
• Uses: suzuki reaction

Technology Process of Cyclopenten-1-ylboronic acid

There total 6 articles about Cyclopenten-1-ylboronic 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: 78.0%

1-bromocyclopentene (1192-04-7) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → cyclopenten-1-ylboronic acid (850036-28-1)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; at 40 - 55 ℃; Inert atmosphere;

Reference yield: 40.0%

Trimethyl borate (121-43-7,63156-11-6) + cyclopentanone p-tolylsulfonylhydrazone (17529-98-5) → cyclopenten-1-ylboronic acid (850036-28-1)

Guidance literature:

cyclopentanone p-tolylsulfonylhydrazone; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at -78 - 20 ℃; for 3h;

Trimethyl borate; In hexane; at -78 - 20 ℃; for 2h;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.9b02697

Reference yield:

cyclopentanone (120-92-3) → cyclopenten-1-ylboronic acid (850036-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 6 h / 60 °C

2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane / 3 h / -78 - 20 °C

2.2: 2 h / -78 - 20 °C

2.3: 2 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In methanol; hexane;

DOI:10.1021/acs.orglett.9b02697

upstream raw materials:

2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

1-bromocyclopentene

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-(carboxymethoxy)cyclopentadiene