2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 1309982-39-5
• Molecular Formula: C₁₄H₂₀BNO₄
• Molecular Weight: 277.128
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50694493
• Wikidata: Q82623603
• Mol file: 1309982-39-5.mol

Synonyms:1309982-39-5;2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;6-(1,3-Dioxolan-2-yl)pyridine-3-boronic acid pinacol ester;MFCD12198148;DTXSID50694493;WNNGBTVWYXWIEC-UHFFFAOYSA-N;AKOS015950030;FD10333;PS-12953;SY255337;CS-0329053;2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

Chemical Property of 2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property:

• Boiling Point: 396.8±42.0 °C(Predicted)
• PKA: 4?+-.0.31(Predicted)
• PSA: 49.81000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.42620
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 277.1485383
• Heavy Atom Count: 20
• Complexity: 341

Purity/Quality:

95+% ^*data from raw suppliers

2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)C3OCCO3

Technology Process of 2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 4 articles about 2-(1,3-Dioxolan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 49.0%

5-bromo-2-(1,3-dioxolane-2-yl)pyridine (884495-16-3) + 2,3-dimethyl-2,3-butane diol (76-09-5) + boric acid tributyl ester (688-74-4) → 2-(1,3-dioxolan-2-yl)-5-pyridineboronic acid pinacol ester (1309982-39-5)

Guidance literature:

5-bromo-2-(1,3-dioxolane-2-yl)pyridine; With n-butyllithium; In acetone; toluene; at -78 ℃; for 0.583333h;

boric acid tributyl ester; In tetrahydrofuran; acetone; toluene; at -78 - 20 ℃; for 2h;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran; acetone; toluene; at 20 ℃; for 0.166667h;

DOI:10.1021/acs.inorgchem.8b01157

Reference yield:

2-(1,3-dioxolan-2-yl)pyridine (5693-54-9) + bis(pinacol)diborane (73183-34-3) → 2-(1,3-dioxolan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine + 2-(1,3-dioxolan-2-yl)-5-pyridineboronic acid pinacol ester (1309982-39-5)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3-(2-(2-(dicyclohexylboraneyl)ethyl)phenyl)-1,10-phenanthroline; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In 1,4-dioxane; at 25 ℃; for 0.166667h; Inert atmosphere; Glovebox;

2-(1,3-dioxolan-2-yl)pyridine; In hexane; at 25 ℃; for 18h; Overall yield = 67 %; Overall yield = 0.19 g; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.9b03138

Reference yield:

2-iodo-5-bromopyridine (223463-13-6) → 2-(1,3-dioxolan-2-yl)-5-pyridineboronic acid pinacol ester (1309982-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / -10 °C

2.1: toluene-4-sulfonic acid / toluene / 24 h / Dean-Stark; Reflux

3.1: n-butyllithium / acetone; toluene / 0.58 h / -78 °C

3.2: 2 h / -78 - 20 °C

3.3: 0.17 h / 20 °C

With n-butyllithium; isopropylmagnesium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone; toluene;

DOI:10.1021/acs.inorgchem.8b01157

upstream raw materials:

5-bromo-2-(1,3-dioxolane-2-yl)pyridine

2,3-dimethyl-2,3-butane diol

boric acid tributyl ester

2-iodo-5-bromopyridine

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