2476-68-8

Usage

Uses

Used in Pharmaceutical Industry:
C-ANTHRACEN-9-YL-METHYLAMINE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Organic Compounds Synthesis:
C-ANTHRACEN-9-YL-METHYLAMINE is used as a building block in the creation of organic compounds, leveraging its chemical properties to form complex molecules.
Used in Research and Development:
C-ANTHRACEN-9-YL-METHYLAMINE is used as a subject of study in research and development to explore its chemical and biological properties, potentially leading to new discoveries and applications.
Used in Dye and Pigment Production:
C-ANTHRACEN-9-YL-METHYLAMINE is used in the production of dyes and pigments due to its aromatic nature, contributing to the coloration and stability of these products.
Used in Other Industrial Applications:
C-ANTHRACEN-9-YL-METHYLAMINE has potential uses in various industrial applications, where its reactivity and aromatic structure can be harnessed for specific technical needs.

Upstream product

• 779-02-2 9-methylanthracene 
• 642-31-9 9-anthracene aldehyde 
• 1468-95-7 9-hydroxymethylanthracene 
• 18004-57-4 9-anthracenealdehyde oxime 
• 2417-77-8 9-bromoethylanthracene 
• 94617-21-7 N-(9-anthranylmethyl)phthalimide 
• 195133-98-3 9-(azidomethyl)anthracene 
• 1210-12-4 9-cyanoanthracene 
• 24463-19-2 anthracenylmethyl chloride 

Downstream Products

• 1239619-83-0 8-[(anthracen-9-ylmethyl)-amino]-spiro[3,5]non-7-en-6-one 
• 1942-19-4 (E)‐anthracene‐9‐carbaldehyde oxime 
• 34810-13-4 9-Anthracene carboxamide 
• 1620777-59-4 C₄₇H₄₁N₃O₂ 

Relevant academic research and scientific papers

One-Pot Synthesis of 9-Aminomethylanthracene

A novel method for the preparation of 9-aminomethylanthracene has been developed by the use of ammonium salts in the reductive amination of the 9-formyl anthracene derivative, a reaction which has been examined with a variety of reducing agents, ammonium ion sources, and solvents. The optimized reaction conditions allowed the isolation of the fluorophore in good yields.

N6-(arylalkyl)adenosines. Identification of N6-(9-fluorenylmethyl)adenosine as a highly potent agonist for the adenosine A2 receptor.

Several N6-(arylalkyl)adenosines related to N6-benzyladenosine were synthesized, and their A1 and A2 adenosine receptor binding affinities were determined. The annulated derivative N6-(1-naphthylmethyl)adenosine resulted in a very potent A2 agonist (A1 Ki = 24 nM, A2 Ki = 9.1 nM), whereas N6-(9-anthracenylmethyl)adenosine was virtually inactive (A1 Ki = 9,000 nM, A2 Ki = 29,000 nM). Interestingly, the structurally similar N6-(9-fluorenylmethyl)adenosine was the most potent A2 agonist reported to date, with a Ki of 4.9 nM in A2 binding and 5.1 nM in A1 binding. The homologues N6-9-fluorenyladenosine and N6-[2-(9-fluorenyl)ethyl]adenosine showed little or no activity at either adenosine receptor. Effects of these agents on heart rate and coronary flow in the isolated rat heart paralleled their A1 and A2 binding affinities, respectively. These data suggest that for high affinity at the A2 receptor a planar hydrophobic function at a certain distance and angle from the N6 nitrogen is required.

Cu2 fluorescent sensor based on mesoporous silica nanosphere

Monodisperse mesoporous silica nanosphere (MSN) modified with anthracene derivative, 2-(3-(triethoxysilyl) propylamino)-N-(9-anthryl methyl) acetamide (SGAAn) has been fabricated as a fluorescent sensor (SGAAn-MSN) for the detection of metal ions, which shows an exclusive selectivity to Cu2. Compared with SGAAn, SGAAn-MSN presents a higher sensitivity to Cu2. The loading amount of SGAAn in MSN has a great influence on the detection sensitivity of SGAAn-MSN, which varies with the local concentration and accessibility of SGAAn in the pore channel of MSN. Interference studies indicate that the addition of other metal ions such as Ag+, Cd2 and Pb2 has a negligible effect on the selectivity of SGAAn-MSN to Cu2. The possible mechanism for the sensing behavior of SGAAn-MSN to Cu2 is proposed based on the relation between fluorescence quench degree and Cu2 concentration.

Fluorescent photoinduced electron transfer (PET) sensing of anions using charge neutral chemosensors

We demonstrate for the first time that the charge neutral anthracene based fluorescent sensors 1a-c, having an aromatic or aliphatic thiourea moiety as an anion receptor, show ideal PET sensor behaviour where the anthracene fluorescence emission is select

A ratiometric fluorescent chemodosimeter with selective recognition for sulfite in aqueous solution

(Chemical Equation Presented) A fluorescent chemodosimeter containing a guanidiniocarbonylpyrrole and a 9-(aminomethyl)anthracene moiety has been synthesized. The sensor exhibits ratiometric fluorescence changes for SO 32- over other anions in 90% water/DMSO. The interesting ratiometric fluorescent changes for SO32- are attributed to the fluorescence resonance energy transfer (FRET) and the SO3 2- complex induced photochemical reaction. 2009 American Chemical Society.

Water-soluble amino(ethanesulfonate) and [bis(ethanesulfonate)] anthracenes as fluorescent photoinduced electron transfer (PET) pH indicators and Fe3+ chemosensors

Two novel water-soluble anthracene-based fluorescent indicators appended with amino(ethanesulfonate) groups were designed and synthesised. A monoethanesulfonated or diethanesulfonate ligand is located in the proximity of a tertiary amino moiety separated by a methylene spacer at the 9-position of an anthracene fluorophore. The molecular structure of the monoethanesulfonated species was determined by single crystal X-ray diffraction. The molecules were studied by UV-visible absorption and fluorescence spectroscopy in water as molecular probes for protons and cations. The anthracene probes function according to a photoinduced electron transfer (PET) mechanism based on a 'fluorophore-spacer-receptor' format resulting in blue fluorescence on protonation. The excited state pK?a values were evaluated to be 5.7 and 7.4, respectively, for the di- and monoethanesulfonated anthracenes at a constant ionic strength of 0.1 M NaCl. The monoethanesulfonated indicator exhibits a high fluorescence quantum yield of 0.62 in acidic solution, and an enhancement factor (EF) of 9, while the diethanesulfonated indicator has a more modest fluorescence quantum yield of 0.17 and an EF of 2.4. Under acidic conditions both indicators are susceptible to selective quenching of the fluorescence by Fe3+ with linear responses between 0.6-8.9 mM and 0.3-5.0 mM Fe3+ for the diethanesulfonated and monoethanesulfonated anthracenes, respectively. The lack of a vertex in the Job's plots indicates no metal-ligand complexation suggesting the fluorescence quenching may be due to an inner filter effect from Fe3+ absorbance.

A Phosphoramidite Analogue of Cyclotriphosphate Enables Iterative Polyphosphorylations

An iterative polyphosphorylation approach is described, which is based on a phosphoramidite (P-amidite) derived reagent (c-PyPA) obtained from the cyclization of pyrophosphate with a reactive diisopropylaminodichlorophosphine. This type of reagent is unprecedented as it represents a reactive P-amidite without protecting groups. The reagent proved to be stable in solution over several weeks. Its utility is described in the context of iterative monodirectional and bidirectional polyphosphorylations. The ensuing functionalized cyclotriphosphate can be opened with a variety of nucleophiles providing ready access to diverse functionalized polyphosphate chains of defined length with several tags, including both P-N and P-O labels. Their interaction with exo- and endopolyphosphatases is described.

9-benzyl naphthylamine and synthesis method thereof

The invention discloses 9-benzyl naphthylamine with mild reaction conditions, good atom economy and high yield and a synthesis method of the 9-benzyl naphthylamine. The synthesis method comprises thefollowing steps: dissolving anthracene in dichloromethane, cooling to the temperature of 0 DEG C, adding 1, 1-dichloromethyl ether and titanium tetrachloride, heating to the room temperature, stirring, adding saturated sodium bicarbonate, extracting with dichloromethane to obtain an organic phase, drying, evaporating a solvent under reduced pressure, dissolving tert-butyl carbamate in a mixed solvent of acetonitrile and the dichloromethane, stirring, adding triethylsilane and trifluoroacetic acid, and reacting at room temperature; adding saturated sodium bicarbonate, extracting with dichloromethane to obtain an organic phase, drying, evaporating the solvent under reduced pressure, dissolving in the dichloromethane, adding trifluoroacetic acid, stirring, evaporating the solvent until a solid is obtained, adding the solid in sodium hydroxide, stirring, adding dichloromethane for extraction, drying the obtained organic phase, evaporating the solvent until a solid is obtained so as to obtain the target product.

Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer

The excitation of a RuII photosensitizer in the presence of ascorbic acid leads to the reduction of iminium ions to electron-rich α-aminoalkyl radical intermediates, which are rapidly converted into reductive amination products by thiol-mediated hydrogen atom transfer (HAT). As a result, the reductive amination of carbonyl compounds with amines by photoredox catalysis proceeds in good to excellent yields and with broad substrate scope and good functional group tolerance. The three key features of this work are 1) the rapid interception of electron-rich α-aminoalkyl radical intermediates by polarity-matched HAT in a photoredox reaction, 2) the method of reductive amination by photoredox catalysis itself, and 3) the application of this new method for temporally and spatially controlled reactions on a solid support, as demonstrated by the attachment of a fluorescent dye on an activated cellulose support by photoredox-catalyzed reductive amination.

Photophysics of aromatic thiourea derivatives and their complexes with anions. Fast and ultrafast spectroscopic investigations

In order to collect detailed information on the interaction mechanism between fluorescent thiourea derivatives and anions, 9-[4-(trifluoromethyl) phenylthioureidomethyl]anthracene (1) and the corresponding 10-cyanoanthracene derivative (2) were synthesized and investigated in DMSO and MeCN by using absorption and emission steady state techniques, both in the absence and in the presence of different anions (AcO-, H2PO4 -, HSO4-, and Br-). A wide examination of the mechanism of anion recognition was also performed by time-resolved transient absorption spectroscopy, with nano- and femto-second time resolution. A complete picture of the excited state deactivation pathways of 1 and 2, where the main operative processes were fluorescence, intersystem crossing and internal conversion, was obtained. Even if steady-state measurements suggest that 1 and 2 selectively interact in the ground state with the anions H2PO4- and AcO-, time-resolved investigations demonstrate that the substrates are able to complex all the four anions. The photophysics of such complexes was fully characterized. The anions mainly modify the lifetime of the lowest excited singlet state and, especially in the cases of H2PO4 - and AcO-, the efficiencies of fluorescence emission and triplet formation. In particular, no evidence was found of further deactivation processes such as photoinduced electron transfer, photodissociation, and photoionization. the Owner Societies 2010.