19293-62-0

Basic information

• Product Name: 4,4'-DIMETHOXYBENZHYDRYLAMINE
• Synonyms: 1,1-DI(P-ANISYL)METHYLAMINE;1,1-BIS(4-METHOXYPHENYL)METHANAMINE;4,4'-DIMETHOXYBENZHYDRYLAMINE;4,4''-DIMETHOXYBENZHYDRYLAMINE 97+%;4-Methoxy-α-(4-methoxyphenyl)benzenemethanamine;Bis(4-methoxyphenyl)methaneamine;bis(4-Methoxyphenyl)MethanaMine;Benzenemethanamine,4-methoxy-a-(4-methoxyphenyl)-
• CAS NO: 19293-62-0
• Molecular Formula: C₁₅H₁₇NO₂
• Molecular Weight: 243.3
• Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 19293-62-0.mol

Chemical Properties

• Melting Point: 62°C
• Boiling Point: 386 °C at 760 mmHg
• Flash Point: 187.2 °C
• Appearance: /
• Density: 1.099 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 8.85±0.10(Predicted)
• CAS DataBase Reference: 4,4'-DIMETHOXYBENZHYDRYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIMETHOXYBENZHYDRYLAMINE(19293-62-0)
• EPA Substance Registry System: 4,4'-DIMETHOXYBENZHYDRYLAMINE(19293-62-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 26-36/37/39-61
• HazardClass: IRRITANT
• Hazardous Substances Data: 19293-62-0(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
4,4'-Dimethoxybenzhydrylamine is used as a reagent in various scientific experiments for its reactivity, contributing to the advancement of chemical research and understanding of reaction mechanisms.
Used in Industrial Applications:
4,4'-Dimethoxybenzhydrylamine is used as an intermediate in the synthesis of other chemical compounds, playing a vital role in the production of various industrial products.
Used in Chemical Reactions:
4,4'-Dimethoxybenzhydrylamine is used as a reactant in several chemical reactions, facilitating the formation of desired products and contributing to the development of new chemical processes.
Used in Laboratory Settings:
4,4'-Dimethoxybenzhydrylamine is used as a reference compound in laboratory settings, helping researchers to compare and analyze the properties and behaviors of other similar compounds.

Upstream product

• 5291-48-5 bis(4-methoxyphenyl)methanimine 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-66-3 methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 874-90-8 4-methoxybenzonitrile 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 728-87-0 4,4'-Dimethoxybenzhydrol 
• 126748-44-5 N-[bis(4-methoxyphenyl)methyl]-formamide 
• 19293-72-2 bis(4-methoxyphenyl)methanone O-methyl oxime 
• 7525-23-7 4,4'-dimethoxydiphenylmethyl chloride 
• 54150-63-9 4,4'-dimethoxybenzophenone oxime 

Downstream Products

• 70729-06-5 [Bis-(4-methoxy-phenyl)-methyl]-((2E,4E)-hexa-2,4-dienyl)-amine 
• 70729-07-6 [Bis-(4-methoxy-phenyl)-methyl]-bis-((2E,4E)-hexa-2,4-dienyl)-amine 
• 70729-12-3 [Bis-(4-methoxy-phenyl)-methyl]-((E)-oct-2-enyl)-amine 
• 70729-13-4 [Bis-(4-methoxy-phenyl)-methyl]-(1-vinyl-hexyl)-amine 
• 70729-14-5 [Bis-(4-methoxy-phenyl)-methyl]-bis-((E)-oct-2-enyl)-amine 
• 70729-16-7 [Bis-(4-methoxy-phenyl)-methyl]-(1,5-dimethyl-1-vinyl-hex-4-enyl)-amine 
• 70729-15-6 [Bis-(4-methoxy-phenyl)-methyl]-((E)-3,7-dimethyl-octa-2,6-dienyl)-amine 
• 28216-32-2 1,1-di-p-anisylmethylisothiocyanate 
• 115556-85-9 [Bis-(4-methoxy-phenyl)-methyl]-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-amine 
• 91538-17-9 [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid benzyl ester 
• 111865-78-2 [3-Benzyloxy-2-methyl-prop-(E)-ylidene]-[bis-(4-methoxy-phenyl)-methyl]-amine 
• 129397-35-9 [Bis-(4-methoxy-phenyl)-methyl]-[2-cyclohexyl-eth-(E)-ylidene]-amine 
• 86207-14-9 [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid butyl ester 
• 169698-43-5 [Bis-(4-methoxy-phenyl)-methyl]-[2-methyl-prop-(E)-ylidene]-amine 

Relevant articles and documents

Synthesis and biological evaluation of new C-10 substituted dithranol pleiotropic hybrids

Selective alkylation of the antipsoriatic drug dithranol (DTR) at C-10 with tert-butyl bromoacetate, followed by acid-mediated deprotection, produced the corresponding carboxylic acid 4 which was coupled with selectively protected polyamines (PAs), such as putrescine (PUT), spermidine (SPD) and spermine (SPM), dopamine and aliphatic amines and substituted benzylamines producing a series of DTR-PA hybrids, after acid-mediated deprotection, as well as simple amides. The compounds were tested as antioxidants and inhibitors of lipoxygenase (LOX). The amides 4,4′-dimethoxybenzhydrylamide 13 (86% and 95%), 2,4-dimethoxybenzylamide 12 (87% and 81%) and dodecylamide 9 (98% and 74%), and the hybrid DTR-SPM (7) (93% and 87%), showed the highest antioxidant activity in the DPPH and AAPH assays, whereas the most potent inhibitors of LOX were amide 13 (IC50 = 7 μM), the benzylamide 10 (IC50 = 7.9 μM) and the butylamide 8 (IC50 = 10 μM). Molecular binding studies showed that binding of these derivatives into the hydrophobic domain blocks approach of substrate to the active site, inhibiting soybean LOX. Amide 13 presented the highest anti-inflammatory activity (79.7%). The DTR moiety was absolutely necessary for securing high anti-inflammatory potency. Ethyl ester 3 (IC50 = 0.357 μM) and the amides 9 (IC50 = 0.022 μM) and 13 (IC50 = 0.56 μM) exhibited higher antiproliferative activity than DTR (IC50 = 0.945 μM) on HaCaT keratinocytes whereas amide 13 generally presented better cytocompatibility. Amide 13 is a very promising lead compound for further development as an anti-inflammatory and antiproliferative agent.

Sequential Selective C?H and C(sp3)?+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds

Organophosphonium salts containing C(sp3)?+P bonds are among the most utilized reagents in organic synthesis for constructing C?C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C?H and C(sp3)?+P bond functionalizations. In the present study, C?H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one-pot, four-component cross-coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3)?+PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late-stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.

Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis

An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst

Diarylmethylamido bis(phenols) have been subjected to peptide-catalyzed, enantioselective bromination reactions. Desymmetrization of compounds in this class has been achieved such that enantioenriched products may be isolated with up to 97:3 er. Mechanist

Discovery of N-[Bis(4-methoxyphenyl)methyl]-4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamide (MK-8617), an Orally Active Pan-Inhibitor of Hypoxia-Inducible Factor Prolyl Hydroxylase 1-3 (HIF PHD1-3) for the Treatment of Anemia

The discovery of novel 4-hydroxy-2-(heterocyclic)pyrimidine-5-carboxamide inhibitors of hypoxia-inducible factor (HIF) prolyl hydroxylases (PHD) is described. These are potent, selective, orally bioavailable across several species, and active in stimulati

Organomediated Enantioselective 18F Fluorination for PET Applications

The first organomediated asymmetric 18F fluorination has been accomplished using a chiral imidazolidinone and [18F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched 18F-labeled α-fluoroaldehydes (>90 % ee), which are versatile chiral 18F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[18F]fluoroglutamic acid.

Pd-catalyzed enantioselective C-H iodination: Asymmetric synthesis of chiral diarylmethylamines

An enantioselective C-H iodination reaction using a mono-N-benzoyl- protected amino acid has been developed for the synthesis of chiral diarylmethylamines. The reaction uses iodine as the sole oxidant and proceeds at ambient temperature and under air.

THERAPEUTIC METHODS

The present invention relates to methods of treatment of diseases mediated by ROR?.

Organic Compounds

A compound of formula (I) or stereoisomers or pharmaceutically acceptable salts thereof, and their preparation and use as pharmaceuticals wherein R1, R2 and R3 are as defined herein.

Direct access to N-H-aziridines from asymmetric catalytic aziridination with borate catalysts derived from vaulted binaphthol and vaulted biphenanthrol ligands

The asymmetric catalytic aziridination reaction (AZ reaction) of N-dianisylmethylimines (N-DAM-imines) with ethyl diazoacetate is developed with chiral catalysts prepared from triphenylborate and both the vaulted binaphthol (VANOL) and vaulted biphenanthrol (VAPOL) ligands. Catalysts derived from both ligands were equally effective in terms of asymmetric induction, but the VANOL catalyst was slightly faster. Up to 400 turnovers could be achieved with the VANOL catalyst while still maintaining ≥90% ee in the aziridine product. The ligand could be recovered in 95% yield with no loss in optical purity. Excellent asymmetric inductions were observed with arylimines, and although slightly lower inductions were observed for alkyl-substituted imines, the optical purity of the aziridines from all of the imine substrates could be enhanced to ≥ 99% ee with a single crystallization. Methods were developed for deprotection of the N-DAM-aziridines under acidic conditions without causing an acid-promoted opening of the ring. Excellent yields of the N-H-aziridines could be obtained with both alkyl- and aryl-substituted aziridines. Finally, activation of the N-H-aziridines was achieved with Boc, tosyl, and Fmoc groups. The activated aziridines can be converted to β3-amino esters, and unexpectedly, the N-Boc-protected aziridine-2-carboxylate 16b with a phenyl substituent in the 3-position cis to the ester group was found to undergo ring expansion to a mixture of cis- and trans-oxazolidinones.