2,5-Dichloropyridine-4-boronic acid

Base Information

• Chemical Name: 2,5-Dichloropyridine-4-boronic acid
• CAS No.: 847664-64-6
• Molecular Formula: C₅H₄BCl₂NO₂
• Molecular Weight: 191.809
• Hs Code.: 2933399090
• European Community (EC) Number: 677-051-6
• ChEMBL ID: CHEMBL3236592
• DSSTox Substance ID: DTXSID30479301
• Nikkaji Number: J2.142.731D
• Wikidata: Q72467912
• Mol file: 847664-64-6.mol

Synonyms:2,5-Dichloropyridine-4-boronic acid;847664-64-6;(2,5-Dichloropyridin-4-yl)boronic acid;2,5-dichloropyridin-4-ylboronic acid;MFCD06798254;2,5-dichloropyridin-4-yl-4-boronic acid;2,5-DICHLORO-4-PYRIDINEBORONIC ACID;Boronic acid, (2,5-dichloro-4-pyridinyl)-;2,5-Dichloropyridine-4-BoronicAcid;SCHEMBL2714951;CHEMBL3236592;DTXSID30479301;BEJJMDOFMZCRST-UHFFFAOYSA-N;2,5-Dichloro-4-pyridylboronic Acid;AKOS006344176;AB29872;AM90134;CS-W020545;GS-5706;s10010;4-CHLOROANILIDOPHOSPHORYLDICHLORIDE;AC-33486;SY022314;D5082;FT-0685681;EN300-6769080;J-507323;Z1201623855;2,5-Dichloropyridine-4-boronic Acid (contains varying amounts of Anhydride)

Chemical Property of 2,5-Dichloropyridine-4-boronic acid

Chemical Property:

• Appearance/Colour: White to cream-colored crystalline powder
• Vapor Pressure: 4.29E-06mmHg at 25°C
• Melting Point: 150 °C
• Refractive Index: 1.58
• Boiling Point: 368.9 °C at 760 mmHg
• PKA: 6.27±0.58(Predicted)
• Flash Point: 176.9 °C
• PSA: 53.35000
• Density: 1.56 g/cm³
• LogP: 0.06820
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 190.9712139
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dichloropyridine-4-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=NC=C1Cl)Cl)(O)O

Technology Process of 2,5-Dichloropyridine-4-boronic acid

There total 2 articles about 2,5-Dichloropyridine-4-boronic acid 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: 56.0%

2,5 dichloropyridine (16110-09-1) → (2,5-dichloropyridin-4-yl)boronic acid (847664-64-6)

Guidance literature:

2,5 dichloropyridine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -80 ℃; for 1h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -80 - 20 ℃;

DOI:10.1016/j.tet.2004.12.006

Reference yield:

2,5 dichloropyridine (16110-09-1) + Triisopropyl borate (5419-55-6) → (2,5-dichloropyridin-4-yl)boronic acid (847664-64-6)

Guidance literature:

2,5 dichloropyridine; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/acschemneuro.7b00153

Reference yield:

(2,5-dichloropyridin-4-yl)boronic acid (847664-64-6) → 7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide (1608503-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / 1,4-dioxane; water / 16 h / 110 °C

2: cesium fluoride / dimethyl sulfoxide / 48 h / 120 °C

3: lithium hydroxide / water; tetrahydrofuran / 12 h / 20 °C

4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; N-ethyl-N,N-diisopropylamine; cesium fluoride; HATU; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2014.03.079

upstream raw materials:

2,5 dichloropyridine

Triisopropyl borate

Downstream raw materials:

7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide

7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(2-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide

C₂₅H₂₂ClFN₆O

7-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide

Refernces

• 1、 Voisin, Anne Sophie,Bouillon, Alexandre,Lancelot, Jean-Charles,Rault, Sylvain. "Efficient synthesis of halohydroxypyridines by hydroxydeboronation". . p. 1417 - 1421. Retrieved 2007/10/03.