Pyridine borane

Base Information

• Chemical Name: Pyridine borane
• CAS No.: 110-51-0
• Deprecated CAS: 67571-42-0,878775-62-3
• Molecular Formula: C5H8BN
• Molecular Weight: 92.9362
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID1051569
• Mol file: 110-51-0.mol

Synonyms:pyridine borane

Chemical Property of Pyridine borane

Chemical Property:

• Appearance/Colour: clear to slightly hazy colorless to amber liquid
• Vapor Pressure: 22.8mmHg at 25°C
• Melting Point: 10-11 °C(lit.)
• Refractive Index: 1.530 - 1.532
• Boiling Point: 1575 ℃
• Flash Point: 21 °C
• PSA: 3.88000
• Density: 0.92 g/cm³
• LogP: -0.89740
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: reacts slowly
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 90.0515043
• Heavy Atom Count: 7
• Complexity: 30.9

Purity/Quality:

99% ^*data from raw suppliers

Borane pyridine complex ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T, T+
• Hazard Codes: F,T,T+
• Statements: 10-15-20-24/25-36/38-44-36/37/38-26
• Safety Statements: 26-36/37-43-45-36/37/39-28A-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: [B].C1=CC=NC=C1
• General Description: The Borane-pyridine complex (PYB) is a reagent used in reductive amination reactions, where it serves as a reducing agent for converting ketones and aldehydes into amines. In comparative studies, PYB demonstrates efficiency and selectivity, though newer derivatives like 5-ethyl-2-methylpyridine borane (PEMB) may offer improved reaction rates and cost-effectiveness, particularly under solvent-free conditions. PYB remains a viable option for such transformations, often performed at ambient or elevated temperatures, with yields confirmed by analytical techniques like GC and NMR.

Technology Process of Pyridine borane

There total 34 articles about Pyridine borane 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: 99.0%

pyridine (110-86-1) + sodium tetrahydroborate (16940-66-2) → borane pyridine (110-51-0)

Guidance literature:

With iodine; In pyridine; byproducts: NaI, H2; addn. of I2 to Na(BH4) in excess C5H5N, removal of excess C5H5N, extn. of residue with CCl4; evapn.;;

DOI:10.1021/ja00989a013

Reference yield: 96.0%

sulfur (10544-50-0) + sodium tetrahydroborate (16940-66-2) → borane pyridine (110-51-0)

Guidance literature:

With pyridine; In pyridine; to NaBH4 in a flask at 10°C is added pyridine, then is slowly added sulfur (2 h); the amine is evapd., to the residue is added benzene, the solvent is after 1 d removed, elem. anal.;

Reference yield: 95.0%

pyridine (110-86-1) + diborane (19287-45-7) → borane pyridine (110-51-0)

Guidance literature:

In pentane; introduction of B2H6 (freshly prepared from (C2H5)2O*BF3 and Na(BH4)) into C5H5N in pentane; removal of solvent;;

DOI:10.1016/0022-1902(68)80283-0

upstream raw materials:

sodium tetrahydroborate

pyridine

hydrogen

diborane

Downstream raw materials:

tris(2-phenylpropyl)borane

cyclohexyltrifluoro-λ⁴-borane potassium salt

pyridine

hydrogen

Refernces

Reductive amination with 5-ethyl-2-methylpyridine borane

10.1016/j.tetlet.2008.06.095

The research focuses on the development and application of a new amine borane complex, 5-ethyl-2-methylpyridine borane (PEMB), for reductive amination reactions of ketones and aldehydes. The study compares PEMB to other reagents like pyridine borane (PYB) and 2-picoline borane (PICB) in terms of efficiency, cost-effectiveness, and reaction conditions. The experiments involved using PEMB in various reductive amination reactions with different aldehyde or ketone/amine pairs, employing a 2:2:1 ratio for the carbonyl, amine, and PEMB, and in some cases, without solvent to increase volume productivity and reduce waste. The reactions were typically carried out at ambient temperature, with some requiring heating to increase the rate. The study analyzed the yields and reaction times of these processes, finding that PEMB was highly effective, selective, and faster than PICB in solvent-less conditions. The analyses used included gas chromatography (GC) to determine yields and nuclear magnetic resonance (NMR) to characterize the products.