932-30-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxybenzylamine is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its ability to form stable compounds with other molecules makes it a valuable building block in the development of new medications.
Used in Chemical Research:
In the field of chemical research, 2-Hydroxybenzylamine is utilized as a reagent and a starting material for the synthesis of various organic compounds. Its unique structure allows for the exploration of new chemical reactions and the creation of novel molecules with potential applications.
Used in Antioxidant Applications:
2-Hydroxybenzylamine is used as a potent γ-ketoaldehyde scavenger, which has been shown to protect cardiac sodium channels (NaV1.5) from oxidant-induced inactivation. This property makes it a promising candidate for the development of antioxidants that can help prevent damage to the heart and other tissues caused by oxidative stress.

Synthesis Reference(s)

Tetrahedron, 48, p. 4301, 1992 DOI: 10.1016/S0040-4020(01)80441-5

InChI:InChI=1/C7H9NO/c8-5-6-3-1-2-4-7(6)9/h1-4,9H,5,8H2/p+1

Upstream product

• 1125-85-5 3,4-dihydro-2H-benzo[e][1,3]oxazin-2-one 
• 94-67-7 salicylaldehyde-oxime 
• 611-20-1 salicylonitrile 
• 64-17-5 ethanol 
• 141-78-6 ethyl acetate 
• 7664-93-9 sulfuric acid 
• 65-45-2 salicylamide 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 90-02-8 salicylaldehyde 
• 390427-07-3 tert-butyl (2-hydroxybenzyl)carbamate 
• 1206675-01-5 (2-hydroxyphenyl)methanaminium acetate 
• 89985-53-5 1-(2-hydroxyphenyl)ethylamine 
• 918885-51-5 (R)-N-(2-hydroxybenzyl)-2-methylpropane-2-sulfinamide 
• 854893-81-5 benzyl 2-hydroxybenzylcarbamate 

Downstream Products

• 55021-91-5 salicyl-urea 
• 3946-40-5 N-(2-hydroxybenzyl)salicylaldimine 
• 5428-91-1 2-aminomethyl-4,6-dibromo-phenol 
• 90-02-8 salicylaldehyde 
• 14723-37-6 2-[(3-nitro-benzylideneamino)-methyl]-phenol 
• 104712-06-3 8,8'-Bis-{[(Z)-2-hydroxy-benzylimino]-methyl}-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol 
• 157840-48-7 2-[(6-Amino-5-nitro-pyridin-2-ylamino)-methyl]-phenol 
• 106553-21-3 hydroxy-o-hyba 
• 159591-72-7 2-allyl-N,N'-bis(2-hydroxybenzyl)malondiamide 
• 14680-15-0 2-(1'-methylethyl)-3,4-dihydro-2H-1,3-benzoxazine 
• 120-65-0 ortho-dimethylaminomethylphenol 
• 73428-20-3 2-(((4-hydroxyphenethyl)imino)methyl)phenol 
• 390427-07-3 tert-butyl (2-hydroxybenzyl)carbamate 
• 439798-42-2 8-bromo-[1,6]naphthyridine-2-carboxylic acid 2-hydroxy-benzylamide 

Relevant academic research and scientific papers

Fabrication of ω-Transaminase@Metal-Organic Framework Biocomposites for Efficiently Synthesizing Benzylamines and Pyridylmethylamines

In this study, ten ω-transaminases (ω-TAs) have been investigated to efficiently catalyze the synthesis of twenty-four functionalized benzylamines and pyridylmethylamines. We optimized the reactions, screened suitable amino donors and compared ω-transaminases activities for all aromatic aldehyde substrates. Under the optimized conditions, eighteen aromatic amines have been obtained with 60.4%–96.6% conversions and isolated only via simple extraction and recrystallization with 18.5%–81% yields on a preparative scale. Furthermore, we first immobilized the Bm-STA onto the MOFs via the physical adsorption to overcome the limitation of free enzyme and improve their industrial applications. The obtained Bm-STA/UiO-66-NH2 composites exhibited not only high enzymes loading (80.4 mg g?1) and enzyme activity recovery (95.8%), but also the better reusability, storage stability, pH stability and the tolerance to acetone and DMF.

Comparative account of catalytic activity of Ru- and Ni-based nanocomposites towards reductive amination of biomass derived molecules

This work includes an effective comparison of metallic ruthenium and nickel nanoparticles loaded on montmorillonite clay (MMT) for reductive amination reaction of biomass-derived molecules. It comprises an eco-friendly reaction using water as a solvent, utilizing molecular hydrogen and liquor ammonia (25% aq. solution) for the synthesis of primary amines from bio-derived aldehydes within 3–10 h of reaction time. Various parameters such as temperature, hydrogen pressure, substrate/ammonia concentration ratio, and reaction time were optimized while comparing the selectivity of primary amines for both catalysts. The applicability scope of these catalysts was explored with a library of aryl and heterocyclic aldehydes. The reductive amination of crude furfural extracted from biomass feedstock (rice husk) and pure xylose sugar was tested, showing yields in the range of 11–36%, to show the wider industrial scope of both nanocomposites. Gram scale conversion was also carried out to showcase the bulk scalability of the Ru/MMT catalyst.

Self-regulated catalysis for the selective synthesis of primary amines from carbonyl compounds

Most current processes for the general synthesis of primary amines by reductive amination are performed with enormously excessive amounts of hazardous ammonia. It remains unclear how catalysts should be designed to regulate amination reaction dynamics at a low ammonia-to-substrate ratio for the quantitative synthesis of primary amines from the corresponding carbonyl compounds. Herein we show a facile control of the reaction selectivity in the layered boron nitride supported ruthenium catalyzed reductive amination reaction. Specifically, locating ruthenium to the edge surface of layered boron nitride leads to an increased hydrogenation activity owing to the enhanced interfacial electronic effects between ruthenium and the edge surface of boron nitride. This enables self-accelerated reductive amination reactions which quantitatively synthesize structurally diverse primary amines by reductive amination of carbonyl compounds with twofold ammonia. This journal is

Method for synthesizing hydroxybenzylamine

The invention discloses a method for synthesizing hydroxybenzylamine, and belongs to the technical field of organic synthesis. The principle of the method comprises that a demethylation reaction is carried out on methoxybenzylamine under the action of hydrobromic acid; the method is characterized in that methoxybenzylamine and hydrobromic acid are distilled in a reflux state to remove redundant water so as to increase the reaction temperature and increase the concentration of the hydrobromic acid in a reaction mixture, so that the demethylation effect of hydrobromic acid on methoxybenzylamineis enhanced, the reaction time is shortened, and the conversion rate is increased; when no bromomethane gas generation is observed, distillation is continued, excessive hydrobromic acid is recovered to further improve the reaction temperature and the conversion rate, meanwhile, the consumption of the raw material hydrobromic acid is reduced, and the treatment capacity of subsequent steps and the consumption of the raw material sodium hydroxide can also be reduced; therefore, the method has the advantages of simple technological process; the reaction time is short; the product is easy to purify; raw material consumption is low; the reaction yield is high.

Preparation method of salicylamine acetate

The invention discloses a preparation method of salicylamine acetate. The method comprises the following steps: (1) protecting the amino groups of salicylaldehyde having a structure represented by formula 1 to obtain a compound having a structure represented by formula 2; and (2) carrying out acid hydrolysis on the compound of the formula 2, and then reacting the acid-hydrolyzed compound with acetic acid to obtain the salicylamine acetate.

Preparation of a magnetic mesoporous Fe3O4-Pd@TiO2 photocatalyst for the efficient selective reduction of aromatic cyanides

Herein, a hierarchical magnetic mesoporous microsphere was successfully prepared as a photocatalyst via a simple and reproducible route. Typically, Pd nanoparticles (NPs) were evenly dispersed on the surface of a magnetic Fe3O4 microsphere and then coated with a porous anatase-TiO2 shell to form Fe3O4-Pd@TiO2. The core-shell structure could efficiently suppress the conglomeration of Pd NPs during the calcination process at high temperatures as well as the shedding of Pd during the catalytic reaction process in the liquid phase. The as-prepared photocatalyst was characterized by TEM, XRD, XPS, VSM, and N2 adsorption-desorption. Fe3O4-Pd@TiO2 exhibits high photocatalytic activity for the selective reduction of aromatic cyanides to aromatic primary amines in an acidic aqueous solution. Moreover, this magnetic photocatalyst could be easily recovered from the reaction mixture by an external magnet and reused five times without significant reduction in its activity. The superior photocatalytic efficiency of the proposed photocatalyst may be attributed to its high charge separation efficiency and charge transfer rate, which are caused by the Schottky junction and large interface area. The results indicate that the strategy of coating the active noble metal sites with a mesoporous semiconductor shell has a significant potential for application in metal-semiconductor-based photocatalytic reactions.

N,O-Iminoboronates: Reversible Iminoboronates with Improved Stability for Cancer Cells Targeted Delivery

Herein a new class of iminoboronates obtained from 2-acetylbenzene boronic acids and aminophenols is presented. The N,O-ligand topology enabled the formation of an additional B?O bond that locks the boron center in a tetrahedral geometry. This molecular arrangement decisively contributes to improve the construct′s stability in biocompatible conditions and retaining the iminoboronate reversibility in more acidic environments. 2-Acetylbenzene boronic acid was reacted with a fluorescent amino-coumarin to yield a stable and non-fluorescent N,O-iminoboronate. This mechanism was further used to assemble a folate receptor targeting conjugate that selectively delivered the fluorescent amino-coumarin to MDA-MB-231 human breast cancer cells.

MONO AND BICYCLIC RING BORONIC ACID, ESTER AND SALT COMPOUNDS AS INHIBITORS OF P97 COMPLEX

Monocyclic or bicyclic ring boronic acid or ester compounds having an arylalkyi amine substituent at the 4 position and a substituted 5:6 bicyclic group at the 2 position of the mono or bicyclic ring boronic acid or ester as well as optional aliphatic, functional and/or aromatic components substituted at other positions of the mono or bicyclic boronic acid or ester compounds are disclosed. These compounds are inhibitors of the AAA proteasome complex containing p97 and are effective medicinal agents for treatment of diseases associated with the Valosin containing protein and p97 bioactivity such as cancer. Formula (I).

Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia

Described herein are methods for using compounds that activate pyruvate kinase.

Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids

A new (S)-enantioselective ω-transaminase (ω-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged ω-TA (HBV-ω-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-α-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-ω-TA as the catalyst and isopropylamine or (S)-α-MBA as amino donor. Notably, HBV-ω-TA catalyzed the amino transfer to β-keto esters to give optically pure β-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained.