4-Cyclopropylphenylboronic acid

Base Information

• Chemical Name: 4-Cyclopropylphenylboronic acid
• CAS No.: 302333-80-8
• Molecular Formula: C9H11BO2
• Molecular Weight: 161.996
• Hs Code.: 2931900090
• European Community (EC) Number: 828-108-0
• DSSTox Substance ID: DTXSID60385961
• Wikidata: Q72461059
• Mol file: 302333-80-8.mol

Synonyms:4-CYCLOPROPYLPHENYLBORONIC ACID;302333-80-8;(4-cyclopropylphenyl)boronic Acid;4-CYCLOPROPYL-BENZENEBORONIC ACID;Boronic acid, (4-cyclopropylphenyl)-;Boronic acid, B-(4-cyclopropylphenyl)-;MFCD01309064;4-Cyclopropyl-phenylboronic acid;(4-Cyclopropylphenyl)boronicacid;SCHEMBL938629;4-cyclopropyl phenylboronic acid;DTXSID60385961;YNLGFXOBRXSMJZ-UHFFFAOYSA-N;CCG-2660;AKOS006276750;AC-30698;AS-46749;SY020549;BB 0262050;CS-0040763;4-cyclopropyl-benzeneboronic acid, AldrichCPR;F10371;EN300-3219449;A899580;J-017837

Chemical Property of 4-Cyclopropylphenylboronic acid

Chemical Property:

• Boiling Point: 320.3 °C at 760 mmHg
• PKA: 8.74±0.10(Predicted)
• Flash Point: 147.5 °C
• PSA: 40.46000
• Density: 1.17 g/cm³
• LogP: 0.24380
• Storage Temp.: Room temperature.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 162.0852098
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

97% ^*data from raw suppliers

4-Cyclopropylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C2CC2)(O)O
• Uses: 4-Cyclopropylphenylboronic Acid is an intermediate used to prepare substituted indoles as PPAR-γ binding agents. It is also used in the synthesis of thienopyrimidine bisphosphonate inhibitors of farnesyl pyrophosphate synthase for potential bone resorption treatment.

Technology Process of 4-Cyclopropylphenylboronic acid

There total 4 articles about 4-Cyclopropylphenylboronic 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: 65.0%

4-Bromophenylboronic acid (5467-74-3) + 5-cyclopropyl-1-aza-5-germabicyclo[3.3.3]undecane → (4-cyclopropylphenyl)boronic acid (302333-80-8)

Guidance literature:

With bis(3,5-bis(trifluoromethyl)phenyl)(2-(2,4,6-triisopropylphenyl)-1H-inden-3-yl)phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In acetonitrile; at 120 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.9b02776

Reference yield: 60.0%

Triisopropyl borate (5419-55-6) + 1-bromo-4-cyclopropylbenzene (1124-14-7) → (4-cyclopropylphenyl)boronic acid (302333-80-8)

Guidance literature:

1-bromo-4-cyclopropylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 0.5h;

Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -70 - -20 ℃;

With hydrogenchloride; In tetrahydrofuran; hexane; water; toluene; at -20 - 20 ℃;

Reference yield: 60.0%

Triisopropyl borate (5419-55-6) → (4-cyclopropylphenyl)boronic acid (302333-80-8)

Guidance literature:

1-bromo-4-cyclopropylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 0.5h;

Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -70 - -20 ℃;

With hydrogenchloride; water; In tetrahydrofuran; hexane; toluene;

upstream raw materials:

Triisopropyl borate

1-bromo-4-cyclopropylbenzene

4-Bromophenylboronic acid

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

Downstream raw materials:

6-(4-cyclopropylphenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

4-cyclopropylaniline