6,9-Dichloro-2-methoxyacridine

Base Information

• Chemical Name: 6,9-Dichloro-2-methoxyacridine
• CAS No.: 86-38-4
• Molecular Formula: C14H9Cl2NO
• Molecular Weight: 278.138
• Hs Code.: 2933990090
• European Community (EC) Number: 201-666-7
• NSC Number: 2951,2095
• UNII: L7V65XW6XU
• DSSTox Substance ID: DTXSID60235331
• Nikkaji Number: J4.940I
• Wikidata: Q72466636
• ChEMBL ID: CHEMBL4443373
• Mol file: 86-38-4.mol

Synonyms:6,9-Dichloro-2-methoxyacridine;86-38-4;3,9-Dichloro-7-methoxyacridine;Halocrin;Halocrine;Acridine, 6,9-dichloro-2-methoxy-;2-Methoxy-6,9-dichloroacridine;L7V65XW6XU;NSC-2095;NSC-2951;EINECS 201-666-7;MFCD00005028;Acridine,9-dichloro-2-methoxy-;6.9-dichloro-2-methoxyacridine;NSC2951;UNII-L7V65XW6XU;BIDD:GT0206;3,9-dichlor-7-methoxyacridin;6,9dichloro-2-methoxyacridine;SCHEMBL2448633;CHEMBL4443373;DTXSID60235331;NSC2095;NSC 2095;NSC 2951;BBL027493;STK793152;AKOS001073195;AM85929;CS-W012297;6,9-Dichloro-2-methoxyacridine, 97%;AS-36170;SY026856;FT-0620879;EN300-17028

Chemical Property of 6,9-Dichloro-2-methoxyacridine

Chemical Property:

• Vapor Pressure: 1.13E-07mmHg at 25°C
• Melting Point: 163-165 °C
• Refractive Index: 1.696
• Boiling Point: 444.3 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 222.5 °C
• PSA: 22.12000
• Density: 1.399 g/cm³
• LogP: 4.70340
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 277.0061193
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

6,9-Dichloro-2-methoxyacridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C3=C(C=C(C=C3)Cl)N=C2C=C1)Cl
• Uses: 6,9-Dichloro-2-methoxyacridine is used to prepare 6-chloro-2-methoxy-acridin-9-ylamine by reacting with phenol and ammonium carbonate. It is used in the preparation of 9-amino-6-chloro-2-methoxyacridine, N'-(6-Chloro-2-methoxy-acridin-9-yl)-heptylamine and N,N'-bis-(6-chloro-2-methoxy-acridin-9-yl)-hexane-1,6-diamine. Further, it is involved in the preparation of 4-aminoquinoline and 9-aminoacridine derivatives by reaction with quinolizidinylalkylamines.

Technology Process of 6,9-Dichloro-2-methoxyacridine

There total 9 articles about 6,9-Dichloro-2-methoxyacridine 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%

4-chloro-2-(4-methoxyphenylamino)benzoic acid (91-38-3) → 6,9-dichloro-2-methoxyacridine (86-38-4)

Guidance literature:

4-chloro-2-(4-methoxyphenylamino)benzoic acid; With trichlorophosphate; at 130 ℃; for 3h;

With ammonia; In chloroform; water; Cooling with ice;

DOI:10.1016/j.bmc.2011.04.053

Reference yield: 93.75%

→ 6,9-dichloro-2-methoxyacridine (86-38-4)

Guidance literature:

With trichlorophosphate; at 100 ℃;

Reference yield:

2,4 dichlorobenzoic acid (50-84-0) → 6,9-dichloro-2-methoxyacridine (86-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / K₂CO₃; Cu; pyridine / pentan-1-ol / 5 h / Heating

2: 77 percent / POCl₃ / 6 h / Heating

With pyridine; copper; potassium carbonate; trichlorophosphate; In pentan-1-ol; 1: Ullmann-Jourdan reactions;

DOI:10.1016/j.tet.2004.05.013

upstream raw materials:

6-chloro-2-methoxyacridone

4-chloro-2-(4-methoxyphenylamino)benzoic acid

methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate

4-methoxy-aniline

Downstream raw materials:

6-chloro-9-(3,4-dihydro-2H-[1]quinolyl)-2-methoxy-acridine

2-methoxyacridine

6-chloro-2-methoxyacridin-9-amine

N-(6-chloro-2-methoxy-acridin-9-yl)-N'-[3-(6-chloro-2-methoxy-acridin-9-ylamino)-propyl]-N'-(3-methoxy-benzyl)-propane-1,3-diamine

Refernces

• 1、 Kimura,Okabayashi,Kato. "Acridine derivatives. III. Preparation and antitumor activity of the novel acridinyl-substituted uracils". . p. 697 - 701. Retrieved 1989.
• 2、 Solomon, V. Raja,Pundir, Sheetal,Le, Hoang-Thanh,Lee, Hoyun. "Design and synthesis of novel quinacrine-[1,3]-thiazinan-4-one hybrids for their anti-breast cancer activity". . p. 1028 - 1038. Retrieved 2018.
• 3、 Zhang, Bin,Dou, Zhende,Xiong, Zheng,Wang, Ning,He, Shan,Yan, Xiaojun,Jin, Haixiao. "Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents". supporting information. . Retrieved 2019/10/28.