4152-92-5

Usage

Uses

Used in Organic Synthesis:
[2-(aminomethyl)phenyl]methanol is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure facilitates the formation of new chemical bonds and the development of novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
[2-(aminomethyl)phenyl]methanol is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and therapeutic agents. Its ability to be incorporated into more complex molecular structures makes it a valuable component in the design and synthesis of pharmaceutical compounds.
Used in Laboratory Research and Development:
[2-(aminomethyl)phenyl]methanol is utilized as a research intermediate in the laboratory setting, where it aids in the exploration of new chemical reactions and the synthesis of novel compounds. Its presence in the lab allows researchers to study its properties and potential applications in various fields.
Used in Chemical Production Process:
[2-(aminomethyl)phenyl]methanol is also employed in the chemical production process, where it serves as a key component in the manufacturing of various chemicals and materials. Its versatility and reactivity make it an essential part of the chemical production pipeline.
Used in Total Synthesis of Adalinine:
[2-(aminomethyl)phenyl]methanol is a useful research intermediate for the total synthesis of Adalinine, a compound with potential applications in the pharmaceutical and chemical industries. Its role in the synthesis process highlights its importance in the development of new and innovative products.

Synthesis

(4-Aminomethyl-phenyl)-methanol hydrochloride salt 4-Hydroxymethyl-benzonitrile (2.0 g, 15 mol) was reduced using Raney nickel (0. 5g) and hydrogen (50 psi) in MeOH: NH3 (100ml) for 20 hours. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford (4-aminomethyl-phenyl)-methanol hydrochloride salt (2.01 g, 98percent) as a white solid of sufficient purity for use without further purification: MS (APCI+) : m/z 138.3 (M+H).

InChI:InChI=1/C8H11NO/c9-5-7-3-1-2-4-8(7)6-10/h1-4,10H,5-6,9H2

Upstream product

• 7115-95-9 4-oxo-3,4-dihydro-(1H)-2,3-benzoxazine 
• 14859-23-5 3,4-dihydro-1H-benzo[d][1,2]oxazine 
• 6538-31-4 1,5-dihydro-2,4,3-benzodioxadiepin-3-oxide 
• 75-05-8 acetonitrile 
• 359010-73-4 5,6-benzo-2-methyl-4,7-dihydro-1,3-oxazepine 
• 7468-67-9 o-formylbenzonitrile 
• 14758-57-7 1,4-dihydro-benzo[d][1,2]oxazine-3-carboxylic acid ethyl ester 
• 91-13-4 α,α'-dibromo-o-xylene 

Downstream Products

• 39976-24-4 4,5-Dihydro-2,4-benzoxazepin-3(1H)-on 
• 60523-78-6 2,2,2-Trichloro-N-(2-hydroxymethyl-benzyl)-acetamidine 
• 198127-14-9 (2-{[2-(1,4-dioxa-spiro[4.5]dec-7-yl)-ethylamino]-methyl}-phenyl)-methanol 
• 871913-12-1 [2-({[(4-methoxyphenyl)methyl]amino}methyl)phenyl]methanol 
• 397870-25-6 1-(2-methyl-benzyl)-1-aza-spiro[4.5]decan-2-one 
• 397870-23-4 1-(2-methyl-benzyl)-1-aza-spiro[5.5]undecan-2-one 
• 17300-02-6 1,2-benzenedimethanamine 
• 39976-43-7 3-oxo-1,5-dihydro-benzo[e][1,3]oxazepine-4-carboxylic acid anilide 
• 182963-62-8 7-ethylamino-4-[2-(hydroxymethyl)benzylamino]-6-nitroquinazoline 
• 496-12-8 isoindoline 
• 1253889-43-8 N⁽¹⁾-(4-butylphenyl)-N⁽²⁾-(2-(hydroxymethyl)benzyl)phthalamide 
• 1258652-35-5 C₂₄H₂₇NO₃ 
• 1333114-86-5 C₁₃H₁₉NO₃ 

Relevant academic research and scientific papers

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.

meta-Selective C?H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand

Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium-catalyzed borylation of a range of common amine-containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta-selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine-containing building blocks of great utility in many applications.

Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Br?nsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles

A novel route to 1,3-oxazaheterocycles based on cooperative Ru-H/Br?nsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Br?nsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst. (Chemical Equation Presented).

Rhodium-catalyzed asymmetric hydrogenation of olefins with PhthalaPhos, a new class of chiral supramolecular ligands

A library of 19 binol-derived chiral monophosphites that contain a phthalic acid diamide group (Phthala- Phos) has been designed and synthesized in four steps. These new ligands were screened in the rhodium-catalyzed enantioselective hydrogenation of prochiral dehydroamino esters and enamides. Several members of the library showed excellent enantioselectivity with methyl 2-acetamido acrylate (6 ligands gave >97% ee), methyl (Z)-2- acetamido cinnamate (6 ligands gave >94% ee), and N-(1-phenylvinyl)acetamide (9 ligands gave >95% ee), whilst only a few representatives afforded high enantioselectivities for challenging and industrially relevant substrates N-(3,4-dihydronaphthalen-1- yl)-acetamide (96% ee in one case) and methyl (E)-2-(acetamidomethyl)-3- phenylacrylate (99% ee in one case). In most cases, the new ligands were more active and more stereoselective than their structurally related monodentate phosphites (which are devoid of functional groups that are capable of hydrogen-bonding interactions). Control experiments and kinetic studies were carried out that allowed us to demonstrate that hydrogen-bonding interactions involving the diamide group of the PhthalaPhos ligands strongly contribute to their outstanding catalytic properties. Computational studies carried out on a rhodium precatalyst and on a conceivable intermediate in the hydrogenation catalytic cycle shed some light on the role played by hydrogen bonding, which is likely to act in a substrate-orientation effect.

Tripodal tris-tacn and tris-dpa platforms for assembling phosphate-templated trimetallic centers

Multidentate tripodal ligands, N(CH2-m-C6H 4-CH2tacn)3 (L1) and N(CH2-o-C 6H4-CH2N(CH2py)2) 3 (L2), have been devised for assembling high-nuclearity metal clusters. By using the same tripodal platform with different ligand appendages, either triazacyclononanes or dipicolylamines, and functionalizing either the ortho or the meta positions on the tris(xylyl) linker arms, discrete trimetal phosphate units of relevance to phosphate-metabolizing trimetallic centers in biology were prepared. Four such compounds, [(CuIICl) 3(HPO4)L1](PF6) (1), [(CuIICl) 3(HAsO4)L1](PF6) (2), Na2[Mn III6MnII2(H2O) 2(HPO4)6(PO4)4(L1) 2] (3), and [CoII3(H2PO 4)Cl2(MeCN)L2](PF6)3 (4), all containing three metal centers bound to a central phosphate or arsenate unit bridging oxygen atoms, have been synthesized and structurally characterized. These results demonstrate the propensity of this novel tripodal ligand platform, in the presence of phosphate or arsenate, to assemble {M3(EO 4)} units and thus structurally mimic trimetallic active sites of proteins involved in phosphate metabolism. Reactivity studies reveal that the tricopper complex 1 is more efficient than monocopper analogues in catalyzing the hydrolysis of 4-nitrophenyl phosphate.

Phthalaphos: Chiral supramolecular ligands for enantioselective rhodium-catalyzed hydrogenation reactions

Interligand hydrogen bonding of chiral monodentate phosphite ligands bearing H-bond donor and acceptor groups leads to formation of supramolecular bidentate ligands, rhodium complexes of which (see picture) afford excellent enantiomeric excesses in catalyzed hydrogenation of classical benchmark and industrially relevant substrates. cod=1,5-cyclooctadiene.

Irreversible inhibition of dipeptidyl peptidase 8 by dipeptide-derived diaryl phosphonates

Dipeptide-derived compounds, bearing various P2 residues and a diaryl pyrrolidin-2-yl phosphonate at the P1 position, were evaluated as dipeptidyl peptidase 8 (DPP8) inhibitors. With these products, irreversible inhibition of DPP8 was observed. To obtain

Investigation into the structure-activity relationship of novel concentration dependent, dual action T-type calcium channel agonists/antagonists

This paper describes the synthesis and biological evaluation of a series of straight chain analogs of a compound (1) that was previously synthesized in our research program. These compounds, which are T-type calcium channel antagonists, exhibits potent anti-proliferative activity against a variety of cancer cells. A structure-activity relationship of these analogs against a variety of cancer cells has provided insight into a logical pharmacophore for this series of compounds. Furthermore, this series of compounds has presented itself as a set of novel, concentration dependent, dual action agonists/antagonists for the T-type calcium channel.

2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives

There are provided according to the invention novel compounds of formula I wherein R1, R2 and R3 are as described in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.