3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

Base Information

• Chemical Name: 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine
• CAS No.: 845885-86-1
• Molecular Formula: C₁₀H₁₄BNO₂
• Molecular Weight: 191.038
• Hs Code.: 2933399990
• European Community (EC) Number: 626-738-9
• DSSTox Substance ID: DTXSID20383347
• Nikkaji Number: J1.140.175I
• Wikidata: Q82175019
• Mol file: 845885-86-1.mol

Synonyms:3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine;845885-86-1;3-Pyridineboronic acid neopentylglycol ester;Pyridine-3-boronic acid neopentylglycol ester;Pyridine-3-boronic acid, neopentyl glycol ester;2-(4-PYRIDIL)-5,5-DIMETHYL-1,3,2-DIOXABORONANE;SCHEMBL4078174;DTXSID20383347;QMEKTOQBDDVVBE-UHFFFAOYSA-N;MFCD03425979;AKOS004116293;AB14739;AT15190;MS-22217;CS-0119983;FT-0644901;pyridine-3-boronic acid neopentyl glycol ester;EN300-132790;3-Pyridineboronic acid neopentylglycol ester, 97%;A840868;5,5-Dimethyl-2-(3-pyridyl)-1,3,2-dioxaborinane;2-(3-Pyridinyl)-5,5-dimethyl-1,3,2-dioxaborinane

Chemical Property of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 0.00114mmHg at 25°C
• Melting Point: 92-96 °C(lit.)
• Refractive Index: 1.491
• Boiling Point: 309.8 °C at 760 mmHg
• PKA: 5.22±0.12(Predicted)
• Flash Point: 141.2 °C
• PSA: 31.35000
• Density: 1.05 g/cm³
• LogP: 0.84980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 191.1117589
• Heavy Atom Count: 14
• Complexity: 189

Purity/Quality:

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

3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=CN=CC=C2
• Uses: 3-Pyridineboronic acid neopentylglycol ester can be used as a reactant: To synthesize N-alkyl-3-boronopyridinium salts by reacting with corresponding alkyl halides. In the ruthenium-catalyzed diastereoselective C-H bond α-arylation of cyclic amines. To prepare 2-(3-pyridyl)benzoxazole by reacting with benzoxazole via copper-catalyzed oxidative arylation reaction. In the Suzuki-Miyaura cross-coupling reaction.

Technology Process of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

There total 3 articles about 3-(5,5-Dimethyl-1,3,2-dioxaborinan-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: 43.0%

3-((2,6-dimethylphenyl)sulfinyl)pyridine + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl) pyridine (845885-86-1)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-); sodium t-butanolate; In 1,4-dioxane; at 110 ℃; for 20h; Inert atmosphere; Glovebox;

DOI:10.1002/chem.202100342

Reference yield:

C13H13NS → 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl) pyridine (845885-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice

2: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-); sodium t-butanolate / 1,4-dioxane / 20 h / 110 °C / Inert atmosphere; Glovebox

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-); 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate; In 1,4-dioxane; dichloromethane;

DOI:10.1002/chem.202100342

Reference yield:

3-iodopyridine (1120-90-7) → 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl) pyridine (845885-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 16 h / 100 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice

3: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-); sodium t-butanolate / 1,4-dioxane / 20 h / 110 °C / Inert atmosphere; Glovebox

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; copper(l) iodide; C₁₅H₂₄N₂*H⁽¹⁺⁾*BF₄^(1-); potassium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane;

DOI:10.1002/chem.202100342

upstream raw materials:

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

3-iodopyridine

Downstream raw materials:

3-HYDROXYPYRIDINE

3-{5-[1-(pyrrolidin-1-yl)cyclohexyl]-1,3-thiazol-2-yl}pyridine

3-hydroxy-1-methylpyridin-1-ium iodide

Refernces