37585-16-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-chloro-benzenemethanol is used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its presence in these compounds is attributed to its anti-inflammatory and anti-cancer activities, which are beneficial in the development of new drugs for treating a range of health conditions.
Used in Drug Discovery and Development:
As a crucial intermediate, 2-Amino-4-chloro-benzenemethanol is utilized in drug discovery and development processes. Its unique chemical structure and properties make it a promising candidate for the creation of novel therapeutic agents, particularly those targeting inflammation and cancer.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Amino-4-chloro-benzenemethanol serves as a key component in the design and synthesis of new chemical entities. Its versatile nature allows for the exploration of various chemical modifications, potentially leading to the discovery of innovative and effective pharmaceuticals.

Upstream product

• 22996-18-5 (4-chloro-2-nitrophenyl)methanol 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 7440-06-4 platinum 
• 60064-34-8 2-Carboethoxy-5-chloroaniline 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 

Downstream Products

• 885609-88-1 N-(5-chloro-2-hydroxymethylphenyl)-2,2-dimethylpropionamide 
• 150097-77-1 N-(Benzylcarbonyl)-5-chloro-2-hydroxymethylaniline 
• 59412-09-8 7-chloro-3-(4-methoxy-phenyl)-1H-quinolin-2-one 
• 124028-67-7 7-chloro-3-(2-methoxyphenyl)-2(1H)-quinolone 
• 150869-44-6 N-[5-chloro-2-(hydroxymethyl)phenyl]acetamide 
• 1051899-82-1 (4-chloro-2-(2-chloropyrimidin-4-ylamino)phenyl)methanol 
• 1046488-99-6 C₂₇H₃₁ClN₂O₂ 
• 553683-61-7 N-[5-chloro-2-(hydroxymethyl)phenyl]formamide 
• 748805-75-6 5-chloro-2-[5-(3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-[1,3,4]oxadiazol-2-ylmethoxymethyl]-phenylamine 
• 1297654-74-0 7-chloro-2-methylquinolin-3-amine 
• 59236-37-2 2-amino-4-chlorobenzaldehyde 
• 1428747-25-4 9-chloro-12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline 
• 1428747-31-2 9-chloro-12-(4-fluorophenyl)-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline 
• 1428747-40-3 9-chloro-12-(4-chlorophenyl)-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline 

Relevant academic research and scientific papers

Synthesis of 3,1-Benzoxazines, 3,1-Benzothiazines and 3,1-Benzoxazepines via N-Arylimino-1,2,3-dithiazoles

o-Aminobenzyl alcohols are converted in two steps into 3,1-benzoxazines 7 and 3,1-benzothiazines 8, and o-aminophenethyl alcohol is converted into 3,1-benzoxazepine 9.

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling

A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Access to 5,6-Spirocycles Bearing Three Contiguous Stereocenters via Pd-Catalyzed Stereoselective [4 + 2] Cycloaddition of Azadienes

We present herein a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones, which represents a rare highly stereoselective cycloaddition of this class of fused azadienes as a two-atom synthon. The use of a phosphoramidite ligand bearing a chiral secondary amine with a simple biphenyl backbone proved to be the key to construct the novel spirocyclic tetrahydroquinoline scaffold containing three contiguous stereocenters as a single diastereomer in high enantioselectivity.

Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines

A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines

We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines

The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.

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.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.