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6-DIMETHYLAMINO-2-NAPHTHALDEHYDE, with the chemical formula C14H13NO, is a light yellow solid that exhibits unique fluorescence properties. It is widely recognized for its role as a fluorescent dye and a reagent in organic synthesis. 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is particularly notable for its applications as a pH indicator and an electron acceptor in chemical reactions, making it a versatile tool in various scientific disciplines.

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  • 173471-71-1 Structure
  • Basic information

    1. Product Name: 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE
    2. Synonyms: 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE;6-(Dimethylamino)-2-naphthalenecarboxaldehyde
    3. CAS NO:173471-71-1
    4. Molecular Formula: C13H13NO
    5. Molecular Weight: 199.25
    6. EINECS: N/A
    7. Product Categories: pharmacetical
    8. Mol File: 173471-71-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 370.4°Cat760mmHg
    3. Flash Point: 151.4°C
    4. Appearance: /
    5. Density: 1.15g/cm3
    6. Vapor Pressure: 1.11E-05mmHg at 25°C
    7. Refractive Index: 1.676
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. PKA: 3.55±0.40(Predicted)
    11. CAS DataBase Reference: 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE(173471-71-1)
    13. EPA Substance Registry System: 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE(173471-71-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 173471-71-1(Hazardous Substances Data)

173471-71-1 Usage

Uses

Used in Analytical Chemistry:
6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is used as a fluorescent dye for the detection and quantification of various analytes due to its distinctive fluorescence properties, which allow for sensitive and selective measurements in analytical processes.
Used in Environmental Monitoring:
In environmental monitoring, 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is employed as a pH indicator, helping to assess the acidity or alkalinity of environmental samples, which is crucial for understanding and managing ecological health.
Used in Bioimaging:
6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is utilized as a fluorescent probe in bioimaging applications, enabling researchers to visualize biological processes and structures with high specificity and sensitivity.
Used in Organic Synthesis:
As a reagent in organic synthesis, 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is used to facilitate various chemical reactions, contributing to the synthesis of complex organic compounds for pharmaceutical, material science, and other research applications.
Used in Chemical Reactions as an Electron Acceptor:
6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is employed as an electron acceptor in chemical reactions, playing a key role in processes that involve electron transfer, which is important in areas such as solar energy conversion and electrochemistry.
Overall, 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE is a multifaceted chemical compound with a broad spectrum of applications across different scientific and industrial fields, underscoring its importance in contemporary research and technological development.

Check Digit Verification of cas no

The CAS Registry Mumber 173471-71-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,3,4,7 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 173471-71:
(8*1)+(7*7)+(6*3)+(5*4)+(4*7)+(3*1)+(2*7)+(1*1)=141
141 % 10 = 1
So 173471-71-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H13NO/c1-14(2)13-6-5-11-7-10(9-15)3-4-12(11)8-13/h3-9H,1-2H3

173471-71-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-(Dimethylamino)-2-naphthaldehyde

1.2 Other means of identification

Product number -
Other names 6-(dimethylamino)naphthalene-2-carbaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:173471-71-1 SDS

173471-71-1Relevant articles and documents

Reaction-based two-photon probes for mercury ions: Fluorescence imaging with dual optical windows

Rao, Alla Sreenivasa,Kim, Dokyoung,Wang, Taejun,Kim, Ki Hean,Hwang, Sekyu,Ahn, Kyo Han

, p. 2598 - 2601 (2012)

For fluorescent imaging of mercury ions in living species, two-photon probes with dual optical windows are in high demand but remain unexplored. Several dithioacetals were evaluated, and a probe was found, which, upon reaction with mercury species, yielded a two-photon dye; this conversion accompanies ratiometric emission changes with a 97-nm shift, enabling fluorescent imaging of both the probe and mercury ions in cells by one- and two-photon microscopy for the first time.

Visualization of Lung Inflammation to Pulmonary Fibrosis via Peroxynitrite Fluctuation

Zhan, Zixuan,Liu, Rui,Chai, Li,Dai, Yongcheng,Lv, Yi

, p. 11461 - 11466 (2019)

Idiopathic pulmonary fibrosis (IPF) is a chronic and progressive lung disease with short survival time. However, owing to the unknown etiology and the lack of sensitive and noninvasive methods, the diagnosis of IPF in the early stage is still full of challenges. Since the levels of oxidative stress in mitochondria are relevant to pulmonary fibrosis, we herein present a simultaneous near-infrared (NIR)-Ia window and ratiometic fluorescent probe, rTPONOO-1, with two-photon and mitochondria-targeting abilities to explore the potential biological roles of peroxynitrite (ONOO-) in different states of lung slices from healthy to lung inflammation and pulmonary fibrosis, and there is a good linear relationship between ratiometric fluorescence changes and the rate of pulmonary fibrosis from hematoxylin and eosin (H&E) and Masson staining. In addition, the therapeutic efficacy of aminoguanidine hemisulfate salt (AG) was also investigated. Thus, rTPONOO-1 has great potential in quickly predicting the progression of pulmonary fibrosis in the early stage and improving effective treatment.

Readily Accessible and Predictable Naphthalene-Based Two-Photon Fluorophore with Full Visible-Color Coverage

Koo, Ja Young,Heo, Cheol Ho,Shin, Young-Hee,Kim, Dahahm,Lim, Chang Su,Cho, Bong Rae,Kim, Hwan Myung,Park, Seung Bum

, p. 14166 - 14170 (2016)

Herein we report 22 acedan-derived, two-photon fluorophores with synthetic feasibility and full coverage of visible wavelength emission. The emission wavelengths were predicted by computational analysis, which enabled us to visualize multicolor images by two-photon excitation with single wavelength, and to design a turn-on, two-photon fluorescence sensor for endogenous H2O2in Raw 264.7 macrophage and rat brain hippocampus ex vivo.

Activatable Fluorescence Probe via Self-Immolative Intramolecular Cyclization for Histone Deacetylase Imaging in Live Cells and Tissues

Liu, Xianjun,Xiang, Meihao,Tong, Zongxuan,Luo, Fengyan,Chen, Wen,Liu, Feng,Wang, Fenglin,Yu, Ru-Qin,Jiang, Jian-Hui

, p. 5534 - 5539 (2018)

Histone deacetylases (HDACs) play essential roles in transcription regulation and are valuable theranostic targets. However, there are no activatable fluorescent probes for imaging of HDAC activity in live cells. Here, we develop for the first time a novel activatable two-photon fluorescence probe that enables in situ imaging of HDAC activity in living cells and tissues. The probe is designed by conjugating an acetyl-lysine mimic substrate to a masked aldehyde-containing fluorophore via a cyanoester linker. Upon deacetylation by HDAC, the probe undergoes a rapid self-immolative intramolecular cyclization reaction, producing a cyanohydrin intermediate that is spontaneously rapidly decomposed into the highly fluorescent aldehyde-containing two-photon fluorophore. The probe is shown to exhibit high sensitivity, high specificity, and fast response for HDAC detection in vitro. Imaging studies reveal that the probe is able to directly visualize and monitor HDAC activity in living cells. Moreover, the probe is demonstrated to have the capability of two-photon imaging of HDAC activity in deep tissue slices up to 130 μm. This activatable fluorescent probe affords a useful tool for evaluating HDAC activity and screening HDAC-targeting drugs in both live cell and tissue assays.

Naphthalene derivatives of a conformationally locked GFP chromophore with large stokes shifts

Baleeva, Nadezhda S.,Khavroshechkina, Anastasia V.,Zaitseva, Elvira R.,Myasnyanko, Ivan N.,Zagudaylova, Marina B.,Baranov, Mikhail S.

, (2019)

The active development of fluorescence microscopy requires an increase in the variety of the dyes and their characteristics. Compounds with a large Stokes shift, i.e., a large difference between the positions of the absorption and emission maxima, have at

Intramolecular charge transfer enhancing strategy based MAO-A specific two-photon fluorescent probes for glioma cell/tissue imaging

Chen, Ding,Fang, Haixiao,Li, Lin,Lim, Kah-Leong,Lu, Xiaomei,Qu, Yunwei,Shi, Riri,Wu, Qiong,Yang, Xuekang,Zhang, Cheng-Wu

, p. 11260 - 11263 (2021/11/09)

MAO-A promotes the proliferation of human glioma cells. Herein, we report a series of MAO-A specific two-photon small molecular fluorescent probes (A1-5) based on an intramolecular charge transfer enhancing strategy. The activity of endogenous MAO-A can be selectively imaged using A3 as a representative probe in different biological samples including human glioma cells/tissues via two-photon fluorescence microscopy. The study provides new tools for the visual detection of glioma. This journal is

ICT-based fluorescent ratiometric probe for monitoring mitochondrial peroxynitrite in living cells

Du, Yuting,Wang, Hongliang,Zhang, Ting,Wei, Wen,Guo, Minmin

supporting information, p. 12915 - 12921 (2021/08/03)

Peroxynitrite (ONOO?) is a reactive oxygen species (ROS) that causes serious damage to living cells and is the cause of a series of human diseases. It is reported that mitochondria are the major site of ONOO?production. Therefore, accurate and rapid detection of intracellular ONOO?is important in pathological processes. Herein, a mitochondria-targeted ratiometric fluorescent probe (DMANI) has been rationally designed based on the coumarin-hemicyanine hybrid framework by regulating the intramolecular charge transfer (ICT) effect. TheDMANIcan capture ONOO?at low concentrationsviadirect addition with the CC bond to give an obvious fluorescent signal change from red to blue based on the ICT process. The possible mechanism for this electrophilic addition process was confirmed using electrospray ionization mass spectrometry (ESI-MS) and1H-NMR spectra.DMANIexhibited a good selectivity, a large Stokes shift (248 nm), a low detection limit (40 nM), and a rapid response (within 20 s) to ONOO?. More importantly,DMANIwas successfully used for ratiometric imaging and monitoring of the fluctuations of mitochondrial ONOO?in living cells.

Multichromatic fluorescence towards aberrant proteinaceous aggregates utilizing benzimidazole-based ICT fluorophores

An, Jusung,Jangili, Paramesh,Lim, Sungsu,Kim, Yun Kyung,Verwilst, Peter,Kim, Jong Seung

, p. 205 - 215 (2021/07/20)

The pathological origin of Alzheimer’s disease (AD) remains uncharted terrain, despite intensive investigation. Discriminating aberrant proteinaceous deposits, such as β-amyloid (Aβ) and (hyperphosphorylated) tau protein by imaging methods, is a vital tool to support investigations towards the network of interacting features that results in AD pathology. In this context, multispectral fluorescence imaging (MSFI) has drawn much attention enabling the distinction of several analytes with merely a single fluorophore emitting a multichromatic fluorescent signal. Herein, we developed three kinds of benzimidazole-derived fluorescent dyes, BZ1–BZ3. The photophysical properties and intramolecular charge transfer (ICT) characteristics of the probes were evaluated in various solvents. Furthermore, a benzimidazole-associated polar-sensitivity displayed multichromatic behavior and enabled the visualization of minute differences in microenvironmental polarity between Aβ and tau aggregates, resulting in different maximal fluorescent emission wavelengths. Indeed, BZ2 demonstrated an approximately 30?nm bathochromic shift in maximal fluorescent emission. All these observations offer a potential for the development of a future generation of benzimidazole-derived ICT-based fluorescent probes.

A Fluorescent Kinase Inhibitor that Exhibits Diagnostic Changes in Emission upon Binding

Fleming, Cassandra L.,Sandoz, Patrick A.,Inghardt, Tord,?nfelt, Bj?rn,Gr?tli, Morten,Andréasson, Joakim

, p. 15000 - 15004 (2019/09/17)

The development of a fluorescent LCK inhibitor that exhibits favourable solvatochromic properties upon binding the kinase is described. Fluorescent properties were realised through the inclusion of a prodan-derived fluorophore into the pharmacophore of an ATP-competitive kinase inhibitor. Fluorescence titration experiments demonstrate the solvatochromic properties of the inhibitor, in which dramatic increase in emission intensity and hypsochromic shift in emission maxima are clearly observed upon binding LCK. Microscopy experiments in cellular contexts together with flow cytometry show that the fluorescence intensity of the inhibitor correlates with the LCK concentration. Furthermore, multiphoton microscopy experiments demonstrate both the rapid cellular uptake of the inhibitor and that the two-photon cross section of the inhibitor is amenable for excitation at 700 nm.

A mitochondria-targeted two-photon fluorogenic probe for the dual-imaging of viscosity and H2O2 levels in Parkinson's disease models

Li, Hao,Xin, Chenqi,Zhang, Gaobin,Han, Xisi,Qin, Wenjing,Zhang, Cheng-Wu,Yu, Changmin,Jing, Su,Li, Lin,Huang, Wei

supporting information, p. 4243 - 4251 (2019/07/16)

Parkinson's disease (PD) is a neurodegenerative disease that seriously affects the quality of life of the patient. Many sources have shown that mitochondrial dysfunction is increasingly appreciated as playing a critical role in the pathogenesis of PD. The mitochondrial microenvironment and H2O2 level are two key parameters that are used to assess the function of mitochondria. Herein, we designed and synthesized a novel two-photon (TP) fluorogenic probe Mito-LX, which could simultaneously monitor changes in the mitochondrial viscosity and H2O2 levels using two different channels. This probe showed a significant response to viscosity changes with red emission at 730 nm and high sensitivity to H2O2 levels with orange emission at 585 nm. Moreover, Mito-LX was successfully applied to living systems (including living cells, zebrafish and Drosophila) for viscosity and H2O2 detection using one- and two-photon fluorescence confocal microscopy.

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