2-Acetyl-6-(dimethylamino)naphthalene

Base Information

• Chemical Name: 2-Acetyl-6-(dimethylamino)naphthalene
• CAS No.: 68520-00-3
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.279
• Hs Code.: 2922399090
• DSSTox Substance ID: DTXSID10571655
• Nikkaji Number: J896.492K
• Wikidata: Q27458293
• Mol file: 68520-00-3.mol

Synonyms:1-[6-(Dimethylamino)naphthalen-2-yl]ethanone;1-[6-(Dimethylamino)-2-naphthyl]ethanone;Acedan;ZINC22047164;

Chemical Property of 2-Acetyl-6-(dimethylamino)naphthalene

Chemical Property:

• Appearance/Colour: Yellow crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 154-156 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• Refractive Index: 1.627
• Boiling Point: 373.832 °C at 760 mmHg
• PKA: 3.80±0.40(Predicted)
• Flash Point: 147.919 °C
• PSA: 20.31000
• Density: 1.105 g/cm³
• LogP: 3.10840
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 213.115364102
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

97% ^*data from raw suppliers

2-Acetyl-6-(dimethylamino)naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C
• Uses: Naphthalene derivative

Technology Process of 2-Acetyl-6-(dimethylamino)naphthalene

There total 20 articles about 2-Acetyl-6-(dimethylamino)naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1-(6-(methylamino)naphthalen-2-yl)ethan-1-one + methyl iodide (74-88-4) → 1-(6-(dimethylamino)naphthalen-2-yl)ethan-1-one (68520-00-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 75 ℃; for 12h;

DOI:10.1021/acs.inorgchem.8b01581

Reference yield: 86.0%

6-methoxy-2-acetylnaphthalene (3900-45-6) + lithium dimethylamide (3585-33-9) → 1-(6-(dimethylamino)naphthalen-2-yl)ethan-1-one (68520-00-3)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In hexane; at 20 ℃; for 16h;

DOI:10.1039/b205224e

Reference yield: 80.0%

ethyleneglycol vinyl ether (764-48-7) + 6?bromo?N,N?dimethylnaphthalen?2?amine (5043-03-8) → 1-(6-(dimethylamino)naphthalen-2-yl)ethan-1-one (68520-00-3)

Guidance literature:

ethyleneglycol vinyl ether; 6?bromo?N,N?dimethylnaphthalen?2?amine; With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; ethylene glycol; triethylamine; at 24 - 145 ℃; Inert atmosphere;

With hydrogenchloride; In dichloromethane; water; at 24 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol3009057

upstream raw materials:

6-methoxy-2-acetylnaphthalene

dimethyl amine

lithium dimethylamide

6-bromo-naphthalen-2-ol

Downstream raw materials:

2-(α-(3,4-diaminophenoxy)acetyl)-6-(dimethylamino)naphthalene

C₂₀H₁₉N₃O₄

6-bromoacetyl-2-dimethylaminonaphthalene

(αS,1S)-α-[N-(1-methyl)benzyl]-β-[6'-(dimethylamino)-2'-naphthoyl]alanine

Refernces

Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells

10.1016/j.cclet.2013.11.024

The research presented in the scholarly article focuses on the development of a highly selective two-photon fluorescent probe, ADNO (2-(α-(3,4-diaminophenoxy)acetyl)-6(dimethylamino)naphthalene), for imaging nitric oxide (NO) in living cells. The probe is designed based on the photoinduced electron transfer (PET) mechanism, utilizing o-phenylenediamine as the NO-sensitive fluorescence modulator and 2-acetyl-6-(dimethylamino)naphthalene (Acedan) as the two-photon fluorophore. The detection of NO is achieved by monitoring the alteration of electron-donating capacity of the o-phenylenediamine moiety, which quenches the fluorescence of Acedan but is reversed in the presence of NO due to the transformation into benzotriazole, thus reviving fluorescence. The probe's rapid response, remarkable fluorescent enhancement, and excellent chemoselectivity for NO over other reactive oxygen/nitrogen species (ROS/RNS) and common metal ions were demonstrated through a series of experiments. These experiments included the synthesis of ADNO, its spectral characterization, and its application in fluorescence imaging of NO in living cells using both one-photon microscopy (OPM) and two-photon microscopy (TPM). The study also assessed the probe's performance at various pH levels and its stability and selectivity in the presence of different ROS/RNS and metal ions. The research utilized various analytical techniques such as NMR, mass spectrometry, UV–vis, and fluorescence spectroscopy to characterize the probe and evaluate its performance.

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