4-(Diethylboranyl)pyridine

Base Information

• Chemical Name: 4-(Diethylboranyl)pyridine
• CAS No.: 93830-58-1
• Molecular Formula: C9H14BN
• Molecular Weight: 147.028
• DSSTox Substance ID: DTXSID00536672
• Nikkaji Number: J1.258.159I
• Wikidata: Q82411405
• Mol file: 93830-58-1.mol

Synonyms:93830-58-1;4-(Diethylboranyl)pyridine;4-(Diethylboryl)pyridine;diethyl(pyridin-4-yl)borane;diethyl (pyridin-4-yl)borane;Pyridine, 4-(diethylboryl)-;diethyl(4-pyridyl)borane;diethyl (4-pyridyl)borane;diethyl(pyrid-4-yl)borane;diethyl(pyridin-4-yl)boron;Diethyl (4-pyridyl borane);SCHEMBL1882995;Diethyl(pyridin-?4-?yl)?borane;DTXSID00536672;LRLPMKLRAJIMNA-UHFFFAOYSA-N;BS-42040;CS-0060265;W17984

Chemical Property of 4-(Diethylboranyl)pyridine

Chemical Property:

• Melting Point: >300 °C(Solv: acetone (67-64-1))
• Boiling Point: 205.9±22.0 °C(Predicted)
• PKA: 5.08±0.10(Predicted)
• PSA: 12.89000
• Density: 0.86±0.1 g/cm3(Predicted)
• LogP: 1.82320
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 147.1219296
• Heavy Atom Count: 11
• Complexity: 95.7

Purity/Quality:

95%, 99% ^*data from raw suppliers

Diethyl(pyridin-4-yl)borane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(CC)(CC)C1=CC=NC=C1
• Uses: Diethyl(pyridin-?4-?yl)?borane is a powerful reducing agent used in the synthesisof non-basic compounds as factor Xa inhibitors. Diethyl(pyridin-?4-?yl)?borane is used for the synthesis of 4-aryl- and 4-heteroarylpyridines by the palladium-catalyzed cross-coupling reaction.

Technology Process of 4-(Diethylboranyl)pyridine

There total 3 articles about 4-(Diethylboranyl)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: 88.0%

4-bromopyridin (1120-87-2) + diethyl methoxy borane (7397-46-8) → diethyl (pyridin-4-yl)borane (93830-58-1)

Guidance literature:

4-bromopyridin; With isopropylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 1h;

diethyl methoxy borane; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1055/s-2002-19775

Reference yield:

4-bromopyridin (1120-87-2) → 3-Diethylboranylpyridine (89878-14-8) + diethyl (pyridin-4-yl)borane (93830-58-1)

Guidance literature:

With n-butyllithium;

Reference yield:

4-bromopyridin (1120-87-2) + triethyl borane (97-94-9) → diethyl (pyridin-4-yl)borane (93830-58-1)

Guidance literature:

With n-butyllithium; In hexane; at -78 - 20 ℃; Inert atmosphere;

upstream raw materials:

4-bromopyridin

diethyl methoxy borane

triethyl borane

Downstream raw materials:

4-(thiophen-3-yl)-pyridine

4-cyclohex-1-enyl-pyridine

2-(pyridin-4-yl)quinoline

4-(2-methylphenyl)pyridine

Refernces

• 1、 Cai, Weiling,Brown Ripin, David H.. "A practical synthesis of pyridylboranes via magnesium-halogen exchange". . p. 273 - 274. Retrieved 2007/10/03.