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

Base Information

• Chemical Name: 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 719268-92-5
• Molecular Formula: C11H15BFNO2
• Molecular Weight: 223.055
• Hs Code.: 2934999090
• European Community (EC) Number: 805-081-3
• DSSTox Substance ID: DTXSID50585993
• Wikidata: Q72476730
• Mol file: 719268-92-5.mol

Synonyms:719268-92-5;3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Fluoropyridine-5-boronic acid pinacol ester;5-Fluoropyridine-3-boronic acid pinacol ester;5-Fluoropyridine-3-boronic acid, pinacol ester;C11H15BFNO2;3-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;3-Fluoropyridine-5-boronic acid, pinacol ester;MFCD07780754;(5-FLUOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;3-Fluoropyridine-5-boronic acid pinacol eater;SCHEMBL975905;3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;DTXSID50585993;VFMTUTYBMBTIGA-UHFFFAOYSA-N;3-Fluoro-5-(4455-tetramethyl-132-dioxaborolan-2-yl)pyridine;AKOS015842141;AB42551;AC-33452;DS-14891;SY025633;AM20061465;CS-0109834;F1026;5-Fluoro-3-pyridylboronic Acid Pinacol Ester;A25352;EN300-160485;J-512509;Z1336745108;2-(5-Fluoro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 5-fluoropyridin-3-ylboronate;3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, AldrichCPR;5-Fluoropyridinyl-3-boronicacidpinacolate;5-Fluoropyridine-3-boronic Acid Pinacol Ester;3-Fluoro-5-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 55.0 to 59.0 °C
• Refractive Index: 1.477
• Boiling Point: 294.487 °C at 760 mmHg
• PKA: 2.80±0.22(Predicted)
• Flash Point: 131.901 °C
• PSA: 31.35000
• Density: 1.1 g/cm³
• LogP: 1.51990
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 223.1179870
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

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

5-Fluoropyridine-3-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 5 articles about 3-Fluoro-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: 92.0%

3-Fluoropyridine (372-47-4) + bis(pinacol)diborane (73183-34-3) → 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (719268-92-5)

Guidance literature:

bis(pinacol)diborane; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn; In para-xylene; at 20 ℃; for 0.5h; Schlenk technique;

3-Fluoropyridine; In para-xylene; at 80 ℃; for 20h; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield: 90.0%

bis(pinacol)diborane (73183-34-3) + trifluoromethanesulfonic acid 5-fluoropyridin-3-yl ester (462652-75-1) → 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (719268-92-5)

Guidance literature:

bis(pinacol)diborane; trifluoromethanesulfonic acid 5-fluoropyridin-3-yl ester; With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; dimethyl sulfoxide; at 90 ℃; for 15h;

With sodium hydroxide; In water; for 0.166667h;

With hydrogenchloride; In water; at 0 ℃; for 0.25h; pH=5;

Reference yield: 81.2%

2,3-dimethyl-2,3-butane diol (76-09-5) + (5-bromopyridin-3-yl)boronic acid (452972-09-7) → 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (719268-92-5)

Guidance literature:

In toluene; at 114 - 118 ℃; for 21h;

upstream raw materials:

bis(pinacol)diborane

trifluoromethanesulfonic acid 5-fluoropyridin-3-yl ester

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

(5-bromopyridin-3-yl)boronic acid

Downstream raw materials:

(4-(3-fluoro-5-(5-fluoropyridin-3-yl)phenyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)methanamine

4-(5-fluoropyridin-3-yl)-2-nitro-6-(pyrimidin-2-yl)benzenamine

(2R,3R)-2-(2,4-difluorophenyl)-3-(2-(3-fluoropyridin-5-yl)-5,6-dihydro[1,2,4]triazolo[1,5-a]piperazine-7(8H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

(2R,3R)-2-(2,4-difluorophenyl)-3-(2-(3-fluoropyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Refernces

• 1、 -. "Azaindole derivative myelocyte proliferation inhibitor, preparation method thereof, and application of inhibitor in pharmacy". Paragraph 0095-0097. . Retrieved 2021/08/07.
• 2、 -. "WNT PATHWAY MODULATORS". Paragraph 0365 - 0367. . Retrieved 2015/07/07.