2-Chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

Base Information

• Chemical Name: 2-Chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine
• CAS No.: 350489-38-2
• Molecular Formula: C₁₀H₁₃BClNO₂
• Molecular Weight: 225.483
• DSSTox Substance ID: DTXSID401195864
• Nikkaji Number: J1.499.389D
• Mol file: 350489-38-2.mol

Synonyms:350489-38-2;2-Chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine;SCHEMBL14674020;DTXSID401195864;MFCD12923438;AKOS022185383;BS-37804;2-Chloro-5-(5,5-dimethyldihydro-4H-1,3,2-dioxaborin-2-yl)pyridine

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

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 225.0727865
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=CN=C(C=C2)Cl

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

There total 3 articles about 2-Chloro-5-(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:

2,2-Dimethyl-1,3-propanediol (126-30-7) + C7H9BClNO2 → 2-chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-pyridine (350489-38-2)

Guidance literature:

2,2-Dimethyl-1,3-propanediol; C₇H₉BClNO₂; In diethyl ether; at 0 ℃; for 1h;

With methanesulfonic acid; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)00279-9

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → 2-chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-pyridine (350489-38-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaNO₂ / aq. HCl / -5 - 0 °C

1.2: 40 percent / CuCl / 20 °C

2.1: butyllithium / diethyl ether / 6 h / -78 °C

2.2: diethyl ether / 12 h / -78 - 20 °C

3.1: diethyl ether / 1 h / 0 °C

3.2: methanesulfonic acid / diethyl ether / 0.5 h / 0 °C

With n-butyllithium; sodium nitrite; In hydrogenchloride; diethyl ether;

DOI:10.1016/S0040-4039(01)00279-9

Reference yield:

5-bromo-2-chloropyridine (53939-30-3) → 2-chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-pyridine (350489-38-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: butyllithium / diethyl ether / 6 h / -78 °C

1.2: diethyl ether / 12 h / -78 - 20 °C

2.1: diethyl ether / 1 h / 0 °C

2.2: methanesulfonic acid / diethyl ether / 0.5 h / 0 °C

With n-butyllithium; In diethyl ether;

DOI:10.1016/S0040-4039(01)00279-9

upstream raw materials:

2,2-Dimethyl-1,3-propanediol

5-bromo-2-pyridylamine

5-bromo-2-chloropyridine

Downstream raw materials:

ethyl (6-chloro-pyridin-3-yl)acetate

2-[3-(6-chloro-pyridin-3-yl)-phenyl]-9-(4-methoxy-phenyl)-[1,10]phenanthroline