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

Base Information

• Chemical Name: 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 452972-13-3
• Molecular Formula: C11H15BBrNO2
• Molecular Weight: 283.961
• Hs Code.: 2934999090
• European Community (EC) Number: 623-807-5
• DSSTox Substance ID: DTXSID80476865
• Nikkaji Number: J2.142.728D
• Wikidata: Q72511859
• Mol file: 452972-13-3.mol

Synonyms:452972-13-3;3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Bromopyridine-5-boronic acid pinacol ester;5-Bromo-3-pyridineboronic acid pinacol ester;3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;5-Bromopyridine-3-boronic acid, pinacol ester;5-Bromopyridine-3-boronic acid,pinacol ester;3-Bromopyridine-5-boronic acid pinacol ester;3-bromo-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;SCHEMBL925705;DIETHYL1-DECYLPHOSPHONATE;DTXSID80476865;JSUVNRWVYRZAOS-UHFFFAOYSA-N;BCP21914;CTA97213;AKOS015834940;AB29855;DS-13750;AM20051192;CS-0041166;FT-0644700;A25342;H11400;EN300-1894073;5-Bromo-3-pyridineboronic acid pinacol ester, 90%;Z2044798540;3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Vapor Pressure: 0.000159mmHg at 25°C
• Melting Point: 63.4-63.8ºC
• Refractive Index: 1.527
• Boiling Point: 341.4 °C at 760 mmHg
• PKA: 2.86±0.22(Predicted)
• Flash Point: 160.3 °C
• PSA: 31.35000
• Density: 1.34 g/cm³
• LogP: 2.14330
• 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: 283.03792
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

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

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 6 articles about 3-Bromo-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: 86.0%

3,5-dibromopyridine (625-92-3) + bis(pinacol)diborane (73183-34-3) → 2-[(5-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (452972-13-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 120 ℃; for 2h;

Reference yield: 75.0%

3-Bromopyridine (626-55-1,163928-56-1) + bis(pinacol)diborane (73183-34-3) → 2-[(5-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (452972-13-3)

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-Bromopyridine; In para-xylene; at 80 ℃; for 24h; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield: 75.0%

3,5-dibromopyridine (625-92-3) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-[(5-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (452972-13-3)

Guidance literature:

3,5-dibromopyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00283-1

upstream raw materials:

3,5-dibromopyridine

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

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

bis(pinacol)diborane

Downstream raw materials:

3-bromo-5-nitro-pyridine

3-bromo-5-(4-chlorophenoxy)pyridine

5-bromopyridine-3-ol

3-bromo-5-(4-methoxyphenyl)pyridine

Refernces

• 1、 Al-Shehimy, Shaymaa,Gramage-Doria, Rafael,Roisnel, Thierry,Trouvé, Jonathan,Zardi, Paolo. "Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity". supporting information. p. 18006 - 18013. Retrieved 2021/05/07.
• 2、 Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel. "meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation". supporting information. p. 8018 - 8023. Retrieved 2019/05/29.