97974-64-6

Usage

Chemical class

Amines

Molecular weight

163.21 g/mol

Derivation

From but-3-en-1-amine and 4-methoxyphenylboronic acid

Applications

a. Synthesis of biologically active molecules and pharmaceuticals
b. Intermediate in organic synthesis
c. Reagent in chemical research

Physical state

Colorless to pale yellow liquid

Odor

Strong amine-like

Safety precautions

Handle and store with care due to reactive and potentially hazardous nature

Upstream product

• 2314-37-6 3-iodo-4-methoxybenzaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 64187-51-5 N-trimethylsilyl(4-methoxy)benzaldimine 
• 123-11-5 4-methoxy-benzaldehyde 
• 762-72-1 allyl-trimethyl-silane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 104-87-0 4-methyl-benzaldehyde 
• 1153630-44-4 C₁₃H₂₀N₂O₃S 
• 874-90-8 4-methoxybenzonitrile 
• 849590-39-2 (±)-N-(4-methoxybenzylidene)-2-methylpropane-2-sulfinamide 
• 2622-05-1 allylmagnesium bromide 
• 49557-76-8 N-(4-methoxybenzylidene)benzenesulfonamide 
• 217947-27-8 N-[1-(4-methoxyphenyl)-3-butenyl]benzenesulfonamide 

Relevant academic research and scientific papers

Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.

Anti-Markovnikov Hydroamination of Homoallylic Amines

The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nucleophiles and homoallylic amines that participate in the reaction is demonstrated.

Synthesis of enantiopure benzyl homoallylamines by indium-mediated barbier-type allylation combined with enzymatic kinetic resolution: Towards the chemoenzymatic synthesis of N-containing heterocycles

Barbier-type indium-mediated allylations of different N, N(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields, The racemic amines were then subj

METHODS OF PREPARING PRIMARY, SECONDARY AND TERTIARY CARBINAMINE COMPOUNDS IN THE PRESENCE OF AMMONIA

The present application relates to novel methods for the preparation of primary, secondary and tertiary carbinamine compounds, particularly the preparation of compounds of formulae I, IV and VI, from a carbonyl compound of formula II in the presence of ammonia or an ammonium equivalent of the formula NH4+X-, by way of allylation, crotylation, arylation, reductive amination and catalytic hydrogenation.

METHODS OF PREPARING SECONDARY CARBINAMINE COMPOUNDS WITH BORONIC ACIDS

The present application relates to novel methods for the preparation of secondary carbinamine compounds, particularly the preparation of secondary carbinamine compounds of the formula Ia, formula Ib or formula IV from aldehydes of the formula II and boronic acids of the formula III or formula V, in the presence of ammonia or an ammonia equivalent of the formula NH4+X-.

α-aminoallylation of aldehydes in aqueous ammonia

α-Aminoallylation of aldehydes in aqueous ammonia has been developed; commercial aqueous ammonia was successfully used, and this method does not require anhydrous conditions thus leading to easy and practical operations.

α-aminoallylation of aldehydes with ammonia: Stereoselective synthesis of homoallylic primary amines

Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon α-amino acid, alloisoleucine, was achieved utilizing this reaction. Copyright

Development and application of allyl, 2-sulfonylethyl and 2-thioethyl carbamate linkers for solid phase N-acyliminium ion chemistry

We have evaluated the allyl, 2-sulfonylethyl (SEC) and 2-thioethyl (TEC) carbamate linker systems for their application in solid supported N-acyliminium ion chemistry. As model reactions the syntheses of both homoallylic amines (via a three component prot

Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support

The synthesis of a library of homoallylic amines is reported. The key step in the synthesis is a one-pot N-acyliminium ion coupling involving a solid phase-bound carbamate, an aldehyde and an allylsilane under Lewis acid conditions.

Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines

Barbier-type allylation of sulfonimines with indium and allyl bromide to give homoallylic sulfonamides can be performed smoothly in organic solvents and in aqueous media. The regio- and the stereoselectivity of the reaction have been examined.