5895-08-9

Usage

Chemical compound

Benzenemethanol, 4-(dimethylamino)-a-2-propenyl-

Chemical compound

Benzenemethanol, 4-(dimethylamino)-a-2-propenyl-

Commonly known as

Benzyl dimethylamine

Physical state

Colorless liquid

Odor

Floral

Odor

Floral

Usage

Fragrance ingredient in perfumes and personal care products

Usage

Fragrance in perfumes and personal care products

Applications

Manufacturing of pharmaceuticals and organic compounds

Applications

Manufacturing pharmaceuticals and organic compounds

Toxicity

Low

Stability

Generally stable under normal storage and handling conditions

Stability

Generally stable under normal storage and handling conditions

Safety

Caution should be used and proper safety measures should be taken when handling this chemical

State

Liquid

Toxicity level

Low

Safety precautions

Caution and proper safety measures required when handling this chemical.

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 762-72-1 allyl-trimethyl-silane 
• 106-95-6 allyl bromide 
• 591-87-7 Allyl acetate 
• 613-94-5 benzoic acid hydrazide 
• 2622-05-1 allylmagnesium bromide 

Relevant academic research and scientific papers

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.

Allylmagnesium Halides Do Not React Chemoselectively because Reaction Rates Approach the Diffusion Limit

Competition experiments demonstrate that additions of allylmagnesium halides to carbonyl compounds, unlike additions of other organomagnesium reagents, occur at rates approaching the diffusion rate limit. Whereas alkylmagnesium and alkyllithium reagents could differentiate between electronically or sterically different carbonyl compounds, allylmagnesium reagents reacted with most carbonyl compounds at similar rates. Even additions to esters occurred at rates competitive with additions to aldehydes. Only in the case of particularly sterically hindered substrates, such as those bearing tertiary alkyl groups, were additions slower.

A mild and efficient three-component synthesis of secondary and tertiary homoallylic hydrazides

A three-component reaction that involved a carbonyl compound, benzoylhydrazine, allyl bromide, and indium in the presence of readily available Zn(ClO4)2·6H2O was developed for the syntheses of secondary and tertiary homoal

Cooperative titanocene and phosphine catalysis: Accelerated C-X activation for the generation of reactive organometallics

The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.

Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides

A protocol for the generation of allyl Grignard reagents via the catalytic activation of allyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired homo allylic alcohols in excellent yields (84-99%). E

METHOD FOR FORMING ALLYLIC ALCOHOLS

A method of performing a chemical reaction includes reacting an allyl donor and a substrate in a reaction mixture, and forming a homoallylic alcohol in the reaction mixture. The substrate may be an aldehyde or a hemiacetal. The reaction mixture includes a ruthenium catalyst, carbon monoxide at a level of at least 1 equivalent relative to the substrate, and water at a level of at least 1 equivalent relative to the substrate, and an amine at a level of from 0 to 0.5 equivalent relative to the substrate. The reaction mixture may also include a halide, and the equivalents of the amine may be similar to those of the halide. The reacting includes maintaining the reaction mixture at a temperature of at least 40°C. The method may be catalytic in metal, environmentally benign, amenable to large-scale applications, and applicable to a wide range of substrates.

Organozinc generation via the titanium-catalyzed activation of alkyl halides

[Chemical Equation Presented] A protocol for the generation of organozinc reagents via catalytic activation of alkyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired products in good to excellent y

Catalytic, nucleophilic allylation of aldehydes with allyl acetate

(Chemical Equation Presented) A new catalytic allylation of aldehydes has been developed that employs allyl acetate as the allylating reagent. Under catalysis by ruthenium trichloride (3 mol %) in the presence of carbon monoxide (30 psi), water (1.5 equiv), and Methylamine (0.1 equiv), a wide range of aromatic, olefinic, and aliphatic aldehydes are efficiently allylated under mild conditions (70 °C, 24-48 h). The stoichiometric byproducts of this reaction are carbon dioxide and acetic acid.

Preparation of allyltin reagents grafted on solid support: Clean and easily recyclable reagents for allylation of aldehydes

The preparation of polymer-supported allyltin reagents was shown to be possible for both unfunctionalized and functionalized allyl units. These reagents were treated with aldehydes in the presence of cerium(III) or indium(III) salts to afford high yields

Barbier-type reaction mediated with tin nano-particles in water

Tin nano-particles are employed in the Barbier-type allylation reaction of carbonyl compounds in water to afford the corresponding homoallylic alcohols in good yields. The in situ generated allylation intermediates, allyltin(II) bromide and diallyltin dib