Borane-2-picoline complex

Base Information

• Chemical Name: Borane-2-picoline complex
• CAS No.: 3999-38-0
• Molecular Formula: C6H10BN
• Molecular Weight: 106.963
• Hs Code.: 29333990
• Mol file: 3999-38-0.mol

Synonyms:2-Picoline,compd. with BH3 (1:1) (7Cl);2-Picoline, compd. with BH3 (6Cl);2-Picoline,compd. with borane (1:1) (8Cl);Pyridine, 2-methyl-, compd. with borane (1:1);Borane, compd. with 2-methylpyridine (1:1);Borane, compd. with 2-picoline(1:1) (8Cl);2-picoline borane;

Chemical Property of Borane-2-picoline complex

Chemical Property:

• Melting Point: 48 °C
• Flash Point: 100°(212°F)
• PSA: 3.88000
• Density: 1.297 g/mL at 25 °C
• LogP: -0.58900
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly sol. in water, cyclohexane, very sol. in methanol, THF, diglyme, and benzene

Purity/Quality:

99% ^*data from raw suppliers

Borane - 2-Methylpyridine Complex ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 14/15-40-36/37/38-26
• Safety Statements: 36/37-43-26-36/37/38-14/15

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Environmentally benign reducing agent. Reactant for: Reductive amination. N-Benzyl-protection of amino acid derivatives by reductive alkylation. Reductive alkoxyamination. Used as reactant for N-Benzyl-protection of amino acid derivatives by reductive alkylation, reductive alkoxyamination, as reducing agent for the labeling of oligosaccharides by reductive amination, synthesis of alkoxyamine derivatives, via reduction of oxime ethers, reductive amination reactions of C1-C10 aldehyde 2,4-dinitrophenylhydrazones, synthesis of various trifluoromethylated amino compounds and an alternative reagent for reductive aminations.

Technology Process of Borane-2-picoline complex

There total 8 articles about Borane-2-picoline complex 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: 98.0%

α-picoline (109-06-8) + dimethylsulfide borane complex (13292-87-0) → 2-picoline borane complex (3999-38-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/acs.joc.1c02729

Reference yield: 94.0%

α-picoline (109-06-8) + sodium tetrahydroborate (16940-66-2) → 2-picoline borane complex (3999-38-0)

Guidance literature:

With iodine; In 1,2-dimethoxyethane; byproducts: NaI, H2; addn. of stoichiometric amounts of I2 in DME to Na(BH4) (15-20% excess) and CH3C5H4N (7-10% excess), stirring for 3h, evapn., extn. with C6H6, evapn.;; dissolving in C6H6, pptn. with hexane;;

Reference yield: 93.9%

α-picoline (109-06-8) + diborane (19287-45-7) → 2-picoline borane complex (3999-38-0)

Guidance literature:

In pentane; introduction of B2H6 (from Na(BH4) and (C2H5)2O*BF3 in diglyme) in the pentane-soln.; evapn. of solvent and excess of substituted pyridine;; recrystn.;;

DOI:10.1021/ja01601a060 DOI:10.1016/0022-1902(68)80283-0

upstream raw materials:

α-picoline

diborane

sodium tetrahydroborate

dimethylsulfide borane complex

Downstream raw materials:

hydrogen

α-picoline

triethyl borate

2-methylpyridine conjugate acid

Refernces

• 1、 Lemaire, Sébastien,Zhdanko, Alexander,van der Worp, Boris A.. "Coordination Chemistry of Borane in Solution: Application to a STING Agonist". . . Retrieved 2022/04/09.
• 2、 García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.. "A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics". supporting information. . Retrieved 2022/01/04.