2-broMocyclopent-1-enylboronic acid

Base Information

• Chemical Name: 2-broMocyclopent-1-enylboronic acid
• CAS No.: 612833-43-9
• Molecular Formula: C5H8BBrO2
• Molecular Weight: 190.832
• Hs Code.: 2931900090
• Mol file: 612833-43-9.mol

Synonyms:(2-bromocyclopenten-1-yl)boronic acid;

Chemical Property of 2-broMocyclopent-1-enylboronic acid

Chemical Property:

• Boiling Point: 283.5±50.0 °C(Predicted)
• PKA: 9.25±0.20(Predicted)
• PSA: 40.46000
• Density: 1.63±0.1 g/cm3(Predicted)
• LogP: 0.83130
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

98%Min ^*data from raw suppliers

(2-Bromocyclopent-1-en-1-yl)boronicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-broMocyclopent-1-enylboronic acid

There total 1 articles about 2-broMocyclopent-1-enylboronic 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: 26.0%

1,2-dibromocyclopentene (75415-78-0) → 2-bromo-1-cyclopenteneboronic acid (612833-43-9)

Guidance literature:

1,2-dibromocyclopentene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at 20 ℃;

With hydrogenchloride; water; In tetrahydrofuran; hexane; at 20 ℃; for 0.25h;

Reference yield: 73.0%

2-bromo-1-cyclopenteneboronic acid (612833-43-9) + ethyl 5-iodo-2-methylbenzoate (612833-45-1) → 3-(2-bromocyclopent-1-enyl)-6-methylbenzoic acid ethyl ester (612833-44-0)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 90 ℃; for 4h;

Reference yield:

2-bromo-1-cyclopenteneboronic acid (612833-43-9) → 3-{2-[5-chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}benzoic acid

Guidance literature:

Multi-step reaction with 4 steps

1.1: Pd(PPh₃)4 / toluene; ethanol / 90 °C

2.1: Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 80 °C

3.1: sodium methylthiolate

3.2: K₂CO₃

4.1: NaOH / ethanol

With sodium hydroxide; sodium thiomethoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; ethanol; water; toluene; 1.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2006.10.041

upstream raw materials:

1,2-dibromocyclopentene

Downstream raw materials:

2-(2-bromo-cyclopent-1-enyl)-4-chloro-1-methoxy-benzene

3-{2-[5-chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}benzoic acid ethyl ester

3-(2-bromocyclopent-1-enyl)-6-methylbenzoic acid ethyl ester

Refernces