9-Chloroacridine

Base Information

• Chemical Name: 9-Chloroacridine
• CAS No.: 1207-69-8
• Molecular Formula: C13H8ClN
• Molecular Weight: 213.666
• Hs Code.: 29379000
• European Community (EC) Number: 214-895-2
• NSC Number: 51950
• DSSTox Substance ID: DTXSID4061622
• Nikkaji Number: J217.057D
• Wikidata: Q72516924
• ChEMBL ID: CHEMBL2180144
• Mol file: 1207-69-8.mol

Synonyms:9-chloroacridine

Chemical Property of 9-Chloroacridine

Chemical Property:

• Appearance/Colour: green to brown solid
• Vapor Pressure: 1.28E-05mmHg at 25°C
• Melting Point: 116-120 °C(lit.)
• Refractive Index: 1.728
• Boiling Point: 379.4 °C at 760 mmHg
• PKA: 3.96±0.10(Predicted)
• Flash Point: 215.2 °C
• PSA: 12.89000
• Density: 1.312 g/cm³
• LogP: 4.04140
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 213.0345270
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

97.0% min(HPLC) ^*data from raw suppliers

9-Chloroacridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)Cl
• Uses: 9-Chloroacridine was employed as chromogenic reagent in the spectrophotometric method for the quantitative determination of dapsone. It was also used in the synthesis of:series of novel chalcones bearing acridine moiety attached to the amino group in their ring Anew acridine derivatives9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives

Technology Process of 9-Chloroacridine

There total 22 articles about 9-Chloroacridine 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: 99.0%

10H-acridin-9-one (578-95-0,790240-54-9) → 9-Chloroacridine (1207-69-8)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.201915181

Reference yield: 98.0%

2-(phenylamino)benzoic acid (91-40-7) → 9-Chloroacridine (1207-69-8)

Guidance literature:

With trichlorophosphate; at 100 ℃; for 0.025h; Microwave irradiation;

DOI:10.1002/poc.1657

Reference yield: 60.0%

aniline (62-53-3) + ortho-chlorobenzoic acid (118-91-2) → 9-Chloroacridine (1207-69-8)

Guidance literature:

aniline; ortho-chlorobenzoic acid; With copper; potassium carbonate; Reflux;

With trichlorophosphate; Reflux;

DOI:10.2174/09298673113209990187

upstream raw materials:

acridine

acridine-9-thione

2-(phenylamino)benzoic acid

10H-acridin-9-one

Downstream raw materials:

9-(piperidin-4-yl)acridine

4-phenyl-2-(acridin-5-yl)-aminothiazole

9-(N⁴-Methyl-N¹-piperazinyl)acridine

9-(N-pyridinium)acridine chloride

Refernces

• 1、 Kudryavtseva,Bogatyrev,Sysoev,Klimova. "Synthesis and Antibacterial Activity of New N9-Substituted Acridine-9-amines". . p. 157 - 159. Retrieved 2019.
• 2、 Sharhan, Olla,Heidelberg, Thorsten,Hashim, Najiahah Mohd,Salman, Abbas Abdulameer,Ali, Hapipah Mohd,Jayash, Soher Nagi. "Synthesis and biological study of acridine-based imidazolium salts". . p. 38995 - 39004. Retrieved 2018.
• 3、 Kivlehan, Francine,Lefoix, Myriam,Moynihan, Humphrey A.,Thompson, Damien,Ogurtsov, Vladimir I.,Herzog, Grégoire,Arrigan, Damien W.M.. "Interaction of acridine-calix[4]arene with DNA at the electrified liquid|liquid interface". . p. 3348 - 3354. Retrieved 2010.
• 4、 Gribble, Gordon W.,Mosher, Michael D.,Jaycox, Gary D.,Cory, Michael,Fairley, Terri A.. "Potential DNA bis-intercalating agents. Synthesis and antitumor activity of N,N-Methylenedi-4,1-cyclohexanediyl- bis(9-acridinamine) isomers". . p. 535 - 546. Retrieved 2014.
• 5、 Dai, Qiuzi,Chen, Jiwei,Gao, Chunmei,Sun, Qinsheng,Yuan, Zigao,Jiang, Yuyang. "Design, synthesis and biological evaluation of novel phthalazinone acridine derivatives as dual PARP and Topo inhibitors for potential anticancer agents". . p. 404 - 408. Retrieved 2020.
• 6、 Yamada,S.,Kaneko,C.. "-". . p. 1273 - 1278. Retrieved 1979.
• 7、 Benoit, Adam R.,Schiaffo, Charles,Salomon, Christine E.,Goodell, John R.,Hiasa, Hiroshi,Ferguson, David M.. "Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity". . p. 3014 - 3017. Retrieved 2014.
• 8、 Kuang, Guotao,Zhang, Meiling,Kang, Shuangshuang,Hu, Dexuan,Li, Xiaoya,Wei, Zuzhuang,Gong, Xue,An, Lin-Kun,Huang, Zhi-Shu,Shu, Bing,Li, Ding. "Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression". . p. 9136 - 9153. Retrieved 2020.
• 9、 -. "N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as preparation method and application thereof". Paragraph 0024; 0025. . Retrieved 2020/05/05.