3999-42-6

Basic information

• Product Name: 2,6-dimethylpyridine--borane
• Synonyms: Boron,(2,6-diMethylpyridine)trihydro-, (T-4)-;2,6-Dimethylpyridine boron complex;2,6-Lutidine-borane;(2,6-DiMethylpyridin-1-iuM-1-yl)trihydroborate;2,6-dimethylpyridine--borane;borane/ 2,6-lutidine complex;Nsc239124
• CAS NO: 3999-42-6
• Molecular Formula: C₇H₁₂BN
• Molecular Weight: 120.98788
• EINECS: 223-645-1
• Mol File: 3999-42-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 2,6-dimethylpyridine--borane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethylpyridine--borane(3999-42-6)
• EPA Substance Registry System: 2,6-dimethylpyridine--borane(3999-42-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: 2926
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 3999-42-6(Hazardous Substances Data)

Usage

General Description

2,6-dimethylpyridine--borane is a chemical compound formed by the reaction of 2,6-dimethylpyridine and borane. It is a colorless, highly flammable liquid with a strong, unpleasant odor. 2,6-dimethylpyridine--borane is commonly used as a complexing agent in organic synthesis and as a reducing agent in chemical reactions. It is also used as a reagent in the production of pharmaceuticals and agrochemicals. 2,6-dimethylpyridine--borane is a versatile compound with a range of applications in various industries. However, it should be handled with caution due to its flammability and potential health hazards.

InChI:InChI=1/C7H12BN/c1-6-4-3-5-7(2)9(6)8/h3-5H,1-2,8H3/q+1

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 13292-87-0 dimethylsulfide borane complex 
• 121-43-7 Trimethyl borate 
• 19287-45-7 diborane 
• 14044-65-6 borane-THF 

Downstream Products

• 108-48-5 2,6-dimethylpyridine 
• 3248-78-0 trioctylborane 
• 17033-11-3 2,6-dimethylpyridinium 
• 11113-50-1 boric acid 

Relevant articles and documents

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Molecular addition compounds. 9. Effect of structure on the reactivities of representative borane-amine complexes in typical reactions such as hydrolysis, hydroboration, and reduction

A number of borane-amine complexes with widely different structural features in the amine portion was prepared and their reactivities toward typical B-H reactions, such as hydrolysis, hydroboration of 1-octene, and reduction of cyclohexanone, were studied. BH3-amine complexes containing an N-phenyl group are hydrolyzed by neutral hydroxylic solvents, while others require a strong acid medium for the hydrolysis. In hydroboration, BH3-N-phenylamine complexes react rapidly with 1-octene in THF at 25°C, while all other types require refluxing THF or toluene for reaction. Again, BH3-N-phenylamine complexes reduce cyclohexanone in THF at 25°C at reasonable rates, while others require acetic acid solvent or mineral or Lewis acids to achieve the desired reduction. Thus, among such borane-amine addition compounds, the BH3-N-phenylamines emerge as unique hydroborating and reducing agents. The results of the present study provide insights into the mechanisms of the hydroboration and reduction reactions. The rates of hydroboration of alkenes with BH3-amine complexes are inversely related to the stability of the adduct, arguing for a prior dissociation of the adduct, followed by the reaction of BH3 with the alkene. The reduction of cyclohexanone with BH3-amine complex in THF proceeds by an analogous dissociation mechanism. In acetic acid or in the presence of mineral or Lewis acids, a bimolecular attack of the BH3-amine complex on the protonated carbonyl group has been considered to be the most viable mechanistic pathway. However, this does not account for the effect of acids on hydrolytic behavior. Consequently, caution is urged in considering possible interpretation of the acid-enhanced reactions of amine-boranes.