23501-93-1

Usage

Uses

Used in Pharmaceutical Industry:
3-Dimethylaminobenzyl alcohol is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactivity allows for the formation of a wide range of derivatives, which can be further utilized in the development of new drugs.
Used in Organic Synthesis:
3-Dimethylaminobenzyl alcohol is used as a versatile building block in organic synthesis. Its reactivity enables the formation of various functional groups, making it a valuable precursor for the synthesis of complex organic molecules.
Used in Preparation of (3-Hydroxymethylphenyl)Trimethylammonium Iodide:
3-Dimethylaminobenzyl alcohol is used in the preparation of (3-hydroxymethylphenyl)trimethylammonium iodide by reacting with methyl iodide. 3-DIMETHYLAMINOBENZYL ALCOHOL has potential applications in various fields, such as in the synthesis of bioactive molecules and as a reagent in chemical reactions.

Upstream product

• 619-22-7 3-(dimethylamino)benzaldehyde 
• 4518-10-9 Methyl 3-aminobenzoate 
• 99-64-9 3-(dimethylamino)benzoic acid 
• 462100-90-9 O²-(3-(dimethylamino)benzyl)-1-(N,N-diethylamino)-diazen-1-ium-1,2-diolate 
• 38803-34-8 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide 
• 16518-64-2 3-(dimethylamino)benzoic acid methyl ester 
• 16518-65-3 m-dimethylaminobenzoic acid ethyl ester 

Downstream Products

• 137865-66-8 Tris-p-dimethylamino-o-hydroxymethyltriphenylmethan 
• 1135120-22-7 C₂₄H₂₅N₃O₅S 
• 1233656-36-4 C₁₈H₂₄NO₄P 
• 14690-00-7 2-O-benzylglycerol 
• 940864-33-5 2-chloro-4-{{[3-(dimethylamino)phenyl]methyl} [(3S)-1-(2-thienyImethyl)-3-pyrrolidinyl]amino} benzonitrile 
• 32360-72-8 10-(4-Dimethylamino-phenyl)-N,N,N',N'-tetramethyl-9,10-dihydro-anthracene-2,7-diamine 
• 303743-62-6 2-(3'-dimethylaminophenyl)-1,3-dihydroxy-4,4,5,5-tetramethylimidazolidine 
• 462100-90-9 O²-(3-(dimethylamino)benzyl)-1-(N,N-diethylamino)-diazen-1-ium-1,2-diolate 
• 828916-46-7 5-(dimethylamino)-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzaldehyde 

Relevant academic research and scientific papers

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.

Chasing ChEs-MAO B Multi-Targeting 4-Aminomethyl-7-Benzyloxy-2H-Chromen-2-ones

A series of 4-aminomethyl-7-benzyloxy-2H-chromen-2-ones was investigated with the aim of identifying multiple inhibitors of cholinesterases (acetyl- and butyryl-, AChE and BChE) and monoamine oxidase B (MAO B) as potential anti-Alzheimer molecules. Starting from a previously reported potent MAO B inhibitor (3), we studied single-point modifications at the benzyloxy or at the basic moiety. The in vitro screening highlighted triple-acting compounds (6, 8, 9, 16, 20) showing nanomolar and selective MAO B inhibition along with IC50 against ChEs at the low micromolar level. Enzyme kinetics analysis toward AChE and docking simulations on the target enzymes were run in order to get insight into the mechanism of action and plausible binding modes.

Photochemical Cleavage of Benzylic C-O Bond Facilitated by an Ortho or Meta Amino Group

The excited state meta effect, also known as the meta-ortho effect, results from selective electron transmission from an electron-donating group to the meta and ortho sites on an aromatic ring in its first excited singlet state. This effect facilitates photochemical cleavage of benzylic C-O or C-N bond to release the corresponding alcohol, carboxylic acid, or amine when an electron-donating amino group is at the meta position, as demonstrated in our recent work of using a 3-diethylaminobenzyl (DEABn) group as an effective photolabile protecting group (PPG). Herein, we demonstrate that an ortho amino group can also facilitate benzylic C-O bond cleavage to release an alcohol or carboxylic acid. However, an amino group at the meta position results in a PPG with better overall chemical and photochemical properties.

Structurally Simple Benzylidene-Type Photolabile Diol Protecting Groups

Two structurally simple photolabile protecting groups for releasing 1,2- and 1,3-diols have been developed. The diols can be protected in high yields and released from their corresponding acetals with high chemical efficiency.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.

Design, synthesis and evaluation of novel HDAC inhibitors as potential antitumor agents

Phenyl imidazolidin-2-one was introduced as the linker for novel HDAC inhibitors. A focused library of 20 compounds was designed and synthesized, among which eight compounds showed equivalent or higher potencies against HDAC1 as compared to vorinostat. In vitro antitumor activity assays in HCT-116, PC-3 and HL-60 cancer cells revealed six compounds with potent antitumor activities, and compound 1o showed 6- to 9-fold higher potencies compared to vorinostat. In an HCT-116 nude mice xenograft model, compound 1o displayed significant antitumor activity in both continuous and intermittent dosing schedules.

Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3

A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.

Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand

A series of modified Hoveyda-Grubbs catalysts incorporating a chelating iodo-benzylidene ligand were prepared and characterized. The presence of electron-withdrawing ring substituents in the para position to the iodide was found to decrease the catalytic activity, revealing that dissociation of the Ru...I-Ar bond is not the rate-determining step.

A new family of halogen-chelated hoveyda-grubbs-type metathesis catalysts

Coordination, not insertion: New ruthenium benzylidenes with a chelating halogen atom were easily prepared and showed excellent stability and activity as metathesis catalysts (see figure). Structure-activity studies reveal that strength of the ruthenium-halogen interaction can be tuned across a wide range to set up a family of latent to active catalysts. Copyright