Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Base Information

• Chemical Name: Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate
• CAS No.: 1025718-91-5
• Molecular Formula: C13H18BNO4
• Molecular Weight: 263.101
• Hs Code.: 2934999090
• European Community (EC) Number: 640-819-6
• DSSTox Substance ID: DTXSID60590391
• Wikidata: Q82484095
• Mol file: 1025718-91-5.mol

Synonyms:1025718-91-5;Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate;3-(METHOXYCARBONYL)PYRIDINE-5-BORONIC ACID, PINACOL ESTER;5-(METHOXYCARBONYL)PYRIDINE-3-BORONIC ACID PINACOL ESTER;methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate;3-(Methoxycarbonyl)pyridine-5-boronic acid pinacol ester;3-(Methoxycarbonyl)pyridin-5-ylboronic acid pinacol ester;MFCD09027079;SCHEMBL1052988;DTXSID60590391;FJOJOCXHLGXEQA-UHFFFAOYSA-N;methyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinic acid methyl ester;AKOS015892427;CS-W004025;MB06752;AM807739;AS-50591;SY015415;EN300-391754;P10659;J-510891;Z2050083284;3-(Methoxycarbonyl)pyridine-5-boronic acid pinacol ester, AldrichCPR;Methyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinic acid methyl ester

Chemical Property of Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

Chemical Property:

• Boiling Point: 371.8±27.0 °C(Predicted)
• PKA: 3.18±0.22(Predicted)
• PSA: 57.65000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 1.16740
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 263.1328882
• Heavy Atom Count: 19
• Complexity: 343

Purity/Quality:

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

3-(Methoxycarbonyl)pyridine-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate

There total 4 articles about Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate 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: 100.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxylic acid methyl ester (1025718-91-5)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 0 - 80 ℃; for 10h;

Reference yield: 94.0%

methyl 3-pyridinecarboxylate (93-60-7) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxylic acid methyl ester (1025718-91-5)

Guidance literature:

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

methyl 3-pyridinecarboxylate; In para-xylene; at 80 ℃; for 18h; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield:

5-bromo-3-pyridinecarboxylic acid (20826-04-4) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxylic acid methyl ester (1025718-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 3 h / 0 °C / Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfuric acid; potassium acetate; In N,N-dimethyl-formamide;

upstream raw materials:

5-bromo-3-pyridine carboxylic acid methyl ester

bis(pinacol)diborane

methyl 3-pyridinecarboxylate

5-bromo-3-pyridinecarboxylic acid

Downstream raw materials:

C₂₀H₁₅Cl₂FN₂O₃

methyl 5-(trifluoromethyl)nicotinate

5,5'-Bis(methoxycarbonyl)-3,3'-bipyridine

N-cyclohexyl-2-(6-(3-ethylureido)-5'-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-3,3'-bipyridin-4-yl)-4-(trifluoromethyl)thiazole-5-carboxamide

Refernces

• 1、 Fan, Lihui,He, Yabing,Wang, Xinxin,Yue, Lianglan,Zhou, Ping. "Lanthanide-Organic Frameworks Featuring Three-Dimensional Inorganic Connectivity for Multipurpose Hydrocarbon Separation". . p. 17249 - 17257. Retrieved 2021/11/17.
• 2、 Herbert, Simon,Kinzel, Tom,Shen, Qilong,Zhang, Wei,Zhao, Haiwei. "Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation". . p. 3596 - 3604. Retrieved 2020/03/23.