2-Chloro-3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 2-Chloro-3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine
• CAS No.: 878194-94-6
• Molecular Formula: C12H14 B Cl N2 O2
• Molecular Weight: 264.519
• Hs Code.: 2934999090
• Mol file: 878194-94-6.mol

Synonyms:2-Chloro-3-cyanopyridine-4-boronic Acid Pinacol Ester

Chemical Property of 2-Chloro-3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 5.81E-07mmHg at 25°C
• Melting Point: 100-101℃
• Refractive Index: 1.521
• Boiling Point: 410.9°C at 760 mmHg
• Flash Point: 202.3°C
• PSA: 55.14000
• Density: 1.2g/cm³
• LogP: 1.90588
• Storage Temp.: ?20°C

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-3-cyanopyridine-4-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Chloro-3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

There total 4 articles about 2-Chloro-3-cyano-4-(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: 77.0%

C6H4BClN2O2 (878194-88-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile (878194-94-6)

Guidance literature:

With magnesium sulfate; In toluene; at 20 ℃; for 12h;

DOI:10.1055/s-2005-922772

Reference yield: 17.0%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + 2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) → 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile (878194-94-6)

Guidance literature:

2-chloro-3-pyridinecarbonitrile; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; for 0.75h;

2,3-dimethyl-2,3-butane diol; With magnesium sulfate; In toluene; for 12h;

Reference yield:

C12H16BClN2O2 → 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile (878194-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / pH 6

2: 77 percent / MgSO₄ / toluene / 12 h / 20 °C

With hydrogenchloride; magnesium sulfate; In toluene;

DOI:10.1055/s-2005-922772

upstream raw materials:

C₆H₄BClN₂O₂

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

2-chloro-3-pyridinecarbonitrile

Triisopropyl borate

Downstream raw materials:

2-chloro-4-(p-tolyl)nicotinonitrile

methyl 4-(2-chloro-3-cyanopyridin-4-yl)benzoate

Refernces

• 1、 -. "IN VITRO COMPOSITIONS COMPRISING HUMAN SAMPLE AND AMYLOID TARGETING AGENT". Paragraph 00325. . Retrieved 2016/06/01.
• 2、 Cailly, Thomas,Fabis, Frédéric,Bouillon, Alexandre,Lema?tre, Stéphane,Sopkova, Jana,De Santos, Olivieira,Rault, Sylvain. "Synthesis of ortho-cyanopyridylboronic acids and esters toward cyano-functionalized bipyridines". . p. 53 - 56. Retrieved 2007/10/03.