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9-Aminoacridine is an acridine analog that acts as a DNA intercalating agent. It is a heterocyclic aromatic amine with a basic nitrogen atom at the 9th position, which allows it to intercalate between the base pairs of DNA, leading to the inhibition of DNA replication and transcription. This property makes it a potential candidate for various applications in different industries.

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  • 90-45-9 Structure
  • Basic information

    1. Product Name: 9-AMINOACRIDINE
    2. Synonyms: 9-acridinamine;9-amino-acridin;9-Aminoakridin;Acridin-9-amine;Acridine, 9-amino-;Aminacrin;Aminoacridine;Izoacridina
    3. CAS NO:90-45-9
    4. Molecular Formula: C13H10N2
    5. Molecular Weight: 194.23
    6. EINECS: 201-995-6
    7. Product Categories: Amines;Aromatics;Heterocycles
    8. Mol File: 90-45-9.mol
  • Chemical Properties

    1. Melting Point: 238-240℃
    2. Boiling Point: 320.68°C (rough estimate)
    3. Flash Point: 233.2°C
    4. Appearance: yellow crystals or powder
    5. Density: 1.268
    6. Vapor Pressure: 4.76E-07mmHg at 25°C
    7. Refractive Index: 1.5014 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: ethanol: hazy
    10. PKA: 9.99(at 20℃)
    11. Water Solubility: 11.65mg/L(24 oC)
    12. Stability: Stable. Incompatible with strong oxidizing agents.
    13. Merck: 14,407
    14. CAS DataBase Reference: 9-AMINOACRIDINE(CAS DataBase Reference)
    15. NIST Chemistry Reference: 9-AMINOACRIDINE(90-45-9)
    16. EPA Substance Registry System: 9-AMINOACRIDINE(90-45-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: 2811
    5. WGK Germany: 3
    6. RTECS: AR7300000
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 90-45-9(Hazardous Substances Data)

90-45-9 Usage

Uses

Used in Pharmaceutical Industry:
9-Aminoacridine is used as an antibacterial agent for its ability to inhibit the replication and transcription of bacterial DNA, leading to the disruption of bacterial growth and proliferation.
Used in Analytical Chemistry:
9-Aminoacridine is used as a MALDI (Matrix-Assisted Laser Desorption/Ionization) matrix for the analysis of low molecular weight anions, such as metabolites, in negative mode. It exhibits low background and good sensitivity, making it a valuable tool for the detection and analysis of these compounds.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

9-AMINOACRIDINE is a moderately strong base. Neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for 9-AMINOACRIDINE are not available; however, 9-AMINOACRIDINE is probably combustible.

Purification Methods

It crystallises from EtOH or acetone and sublimes at 170-180o/0.04mm [Albert & Ritchie Org Synth Coll Vol III 53 1955, for hydrochloride, see below]. [Beilstein 22 H 463, 21 II 280, 21 III/IV 4174.]

Check Digit Verification of cas no

The CAS Registry Mumber 90-45-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 90-45:
(4*9)+(3*0)+(2*4)+(1*5)=49
49 % 10 = 9
So 90-45-9 is a valid CAS Registry Number.
InChI:InChI=1/C13H10N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H,(H2,14,15)

90-45-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (92817)  9-Aminoacridine  matrix substance for MALDI-MS, ≥99.5% (HPLC)

  • 90-45-9

  • 92817-1G

  • 555.75CNY

  • Detail

90-45-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-aminoacridine

1.2 Other means of identification

Product number -
Other names 9-Acridinamine

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:90-45-9 SDS

90-45-9Relevant articles and documents

Synthesis and performance research of selenazole fluorescent dye compound

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Paragraph 0007; 0017, (2020/02/27)

The invention discloses synthesis and performance research of a selenazole fluorescent dye compound; benzoselenazole is used as a recognition group for detecting the HOCl level in cells, and a reliable method is provided for detecting the HOCl level in a biological system in real time. A probe disclosed by the invention has the technical effects that the probe can sensitively and selectively respond to HOCl and detect the HOCl level in tumor living cells, so that the HOCl level in the tumor living cells can be rapidly monitored, and a new method can be provided for early detection of tumors. Compared with other fluorescent compounds, the fluorescent reaction system containing the selenide functional group is simple, has the characteristics of high luminous efficiency, small background interference and the like, and is a fluorescent probe with a wide prospect.

9-Substituted acridines as effective corrosion inhibitors for mild steel: Electrochemical, surface morphology, and computational studies

Li, Hui-Jing,Liu, Ying,Wang, Li-Juan,Wu, Yan-Chao,Zhang, Weiwei,Zhang, Yinlin

, p. 6464 - 6474 (2020/05/13)

Three 9-substituted acridines, namely 9-carboxyacridine (CA), 9-methylacridine (MA), and 9-aminoacridine (AA), were designed and synthesized for the development of effective inhibitors for mild steel corrosion in a 15% HCl solution. The corrosion-resistance ability was tested by weight-loss tests, electrochemical techniques, surface-topography analyses (SEM, SECM, and XPS), and contact angle measurements. The results indicated the inhibition performance followed the order of η(AA) > η(MA) > η(CA), and these acridines acted as mixed type inhibitors with a predominant restrained cathode process. The adsorption of the three acridines on a mild steel surface obeyed the Langmuir adsorption isotherm and involved both physisorption and chemisorption modes. Surface analysis and characterization confirmed the existence of an adsorbed film. Quantum chemical calculations were performed to provide mechanistic insights into the roles of the different substituents (-COOH, -CH3, and -NH2) on the corrosion-inhibition behavior of the three acridines. Molecular dynamics (MD) simulations were carried out to explore the configurational adsorption behavior of these 9-substituted acridines on the Fe(110) surface.

Preparation method of 9-aminoacridine and derivatives thereof

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Paragraph 0043-0047; 0057-0060, (2020/05/01)

The invention relates to a preparation method of 9-aminoacridine and derivatives thereof, and belongs to the technical field of organic synthesis. The preparation method of 9-aminoacridine and derivatives thereof comprises the following steps: adding a compound represented by a formula III into a polar aprotic solvent, then introducing a compound represented by a formula II, carrying out a reaction at a temperature of 70-120 DEG C, and after the reaction is finished, separating and purifying an obtained reaction solution to obtain 9-aminoacridine represented by a formula I and the derivativesthereof. The preparation method can be used for preparing the final product by a one-pot method, and is short in synthetic route, simple and convenient to operate, free of intermediates, high in yieldand low in cost. The method has the advantages of mild reaction conditions, low solvent corrosivity, low price, easy availability and recyclability, ensures the long-term operation of reaction equipment, enhances the operation safety factor, further lowers the production cost, and is suitable for large-scale production and application.

Method for preparing and marking bcl-2 (b-cell lymphoma-2) protein of oral squamous cell carcinoma cells through imine acridine fluorescent probe

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Paragraph 0018-0019, (2019/02/27)

The invention discloses a method for preparing and marking bcl-2 protein of oral squamous cell carcinoma cells through an imine acridine fluorescent probe. Imine acridine is applied to performing fluorescence marking on the bcl-2 protein of the oral squamous cell carcinoma cells and compared on photostability with Fluorescein insothiocyanate (FITC) marks. The applied imine acridine fluorescent probe technically has the advantages that the imine acridine fluorescent probe can reach a maximum emission wavelength of 470 nm under a fluorescence microscope, viewed under a fluorescence inversion microscope, the imine acridine fluorescent probe can clearly mark the bcl-2 protein in tongue cancer ca8113 cells; the method for preparing and marking the bcl-2 protein of the oral squamous cell carcinoma cells through the imine acridine fluorescent probe is high in sensitivity, simple rapid and accurate and is superior to traditional FITC marking methods.

Imine acridine derivative fluorescent probe as well as preparation method and application thereof in detection of MORAb-3-1 antibodies

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Paragraph 0022; 0023; 0024, (2018/11/22)

The invention discloses an imine acridine derivative fluorescent probe as well as a preparation method and application thereof in detection of MORAb-3-1 antibodies. A detection method of the MORAb-3-1antibody is established by combining specificities of antigens and antibodies. The detection method of the MORAb-3-1 antibody has the technical effects that 1, an imine acridine derivative biologicalprobe is combined with HSA (human serum albumin), and then combined with the MORAb-3-1 antibody for the first time, and the MORAb-3-1 antibody is observed under a fluorescent inverted microscope; 2,the combination of the probe and the antigen is judged by utilizing the photophysical and photochemistry natures; 3, the sensitivity is high, the operation is simple, convenient and rapid, and the accuracy is realized; compared with the traditional dye method, the advantages are more excellent. The formula is shown in the description.

Method of preparing imine-type acridine derivative fluorescent probe and detecting thyroglobulin antibody

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Paragraph 0023; 0024, (2019/01/08)

The invention discloses a method of preparing imine-type acridine derivative fluorescent probe and detecting thyroglobulin antibody. A detection method for thyroglobulin antibody is established through specific combination of antigen-antibody. The detection method for thyroglobulin antibody has following technical effects: 1) for the first time, it is put forward that the imine-type acridine probeis combined with the thyroglobulin (Tg) (iodized glycoprotein) and then is combined with the thyroglobulin antibody in order to observe the thyroglobulin antibody under a fluorescent inverted microscope; 2) the combination of antigen-antibody is determined by means of photo-physics and photo-chemistry properties; 3) the method is high in sensitivity, is simple, rapid and accurate, and has advantages than a conventional dye method.

A triazine-phosphite polymeric ligand bearing cage-like P,N-ligation sites: An efficient ligand in the nickel-catalyzed amination of aryl chlorides and phenols

Panahi, Farhad,Roozbin, Fatemeh,Rahimi, Sajjad,Moayyed, Mohammadesmaeil,Valaei, Aria,Iranpoor, Nasser

supporting information, p. 80670 - 80678 (2016/10/12)

A novel P,N-ligand was introduced for efficient Ni-catalyzed amination of aryl chlorides. Reaction of cyanuric acid (1,3,5-triazine-2,4,6-triol) and trichlorophosphine (PCl3) resulted in the production of a new porous material (TPPM) containing triazine rings with phosphite moieties in a sheet morphology. Cavities in the prepared compound create sites on the surface of the material with appropriate ligation character to coordinate with metals for catalytic purposes. The nickel-catalyzed amination of aryl chlorides and of phenols in their 2,4,6-triaryloxy-1,3,5-triazine (TAT) protected form were efficiently accomplished in the presence of this easily prepared and reusable P,N-ligand under mild reaction conditions. More importantly, TPPM was reusable for 5 iterations following this protocol without significantly decreasing in its activity.

9-amino acridine derivative and its synthetic method

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Paragraph 0041, (2017/02/02)

The invention discloses a novel aminoacridine derivative, and particularly relates to a 9-aminoacridine derivative and a synthetic method thereof, belonging to the technical field of organic chemical synthesis. The structure of the 9-aminoacridine derivative is shown in the specification, wherein R1 and R2 are independently selected from H, methoxyl, C1-C10 alkyl and C1-C10 halo-alkyl. The compound has better fluorescence property and can be applied to an organic light-emitting material.

Direct and facile synthesis of 9-aminoacridine and acridin-9-yl-ureas

Borovlev, Ivan V.,Demidov, Oleg P.,Amangasieva, Gulminat A.,Avakyan, Elena K.

supporting information, p. 3608 - 3611 (2016/07/19)

The ability of urea anions to react as nucleophiles with acridine has been investigated. An effective SNH synthesis of 9-aminoacridine was developed using the urea/NaH/DMSO system. However, when mono substituted ureas containing bulky substituents or 1,1-dialkyl substituted ureas were used, products of the SNH reaction of alkyl carbamoyl amination were obtained. Single crystal structure and the tautomerism of selected compound were studied.

NOVEL HDMX INHIBITORS AND THEIR USE FOR CANCER TREATMENT

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Paragraph 0033; 0035; 0036, (2015/11/30)

The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repres

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